From 66051ec7d2ea4d5c2701fca2aa762fcecf82a487 Mon Sep 17 00:00:00 2001
From: filip <44206832+filipkujawa@users.noreply.github.com>
Date: Thu, 6 Aug 2026 20:08:49 -0700
Subject: [PATCH] Cache-safe request assembly: append-only turn context and
 declared cache semantics (#11022)

---
 crates/goose-cli/src/commands/term.rs         |  50 +-
 crates/goose-cli/src/session/mod.rs           |  81 +++-
 .../src/cache_semantics.rs                    | 203 +++++++++
 .../goose-provider-types/src/conversation.rs  |  87 +++-
 .../src/conversation/message.rs               |  13 +
 .../src/formats/anthropic.rs                  | 315 ++-----------
 .../src/formats/databricks.rs                 | 220 +--------
 .../src/formats/openai.rs                     | 245 +---------
 crates/goose-provider-types/src/lib.rs        |   1 +
 .../tests/prefix_invariance.rs                | 428 ++++++++++++++++++
 crates/goose-providers/src/lib.rs             |   4 +-
 crates/goose-providers/src/openai.rs          |   1 -
 crates/goose/src/acp/provider.rs              |  36 +-
 crates/goose/src/agents/agent.rs              |  77 +++-
 crates/goose/src/agents/extension_manager.rs  |   5 +-
 crates/goose/src/agents/moim.rs               | 334 ++++----------
 .../agents/platform_extensions/chatrecall.rs  |   6 +-
 .../platform_extensions/orchestrator.rs       |  19 +-
 crates/goose/src/agents/reply_parts.rs        |   5 +-
 ...nager__tests__all_platform_extensions.snap |   1 +
 ..._agents__prompt_manager__tests__basic.snap |   2 +-
 ..._prompt_manager__tests__one_extension.snap |   2 +-
 ..._prompt_manager__tests__typical_setup.snap |   2 +-
 .../goose/src/agents/state_machine/ops_llm.rs |  33 +-
 .../agents/state_machine/ops_toolcalling.rs   |   2 +
 .../src/agents/state_machine/tests/mod.rs     |  29 ++
 .../agents/state_machine/tests/pipeline.rs    |   1 +
 .../tests/recipe_scheduling_lifecycle.rs      |   7 +-
 crates/goose/src/context_mgmt/mod.rs          | 242 +++++++++-
 crates/goose/src/providers/litellm.rs         |  70 +--
 crates/goose/src/providers/openrouter.rs      |  87 +---
 crates/goose/src/scheduler.rs                 |   8 +-
 .../goose/src/security/adversary_inspector.rs |  39 +-
 crates/goose/src/security/scanner.rs          |  30 ++
 .../goose/src/session/chat_history_search.rs  |  57 ++-
 crates/goose/src/session/session_manager.rs   |  58 ++-
 crates/goose/src/session/session_naming.rs    |   2 +-
 crates/goose/tests/agent.rs                   |  11 +-
 crates/goose/tests/compaction.rs              |   7 +-
 39 files changed, 1589 insertions(+), 1231 deletions(-)
 create mode 100644 crates/goose-provider-types/src/cache_semantics.rs
 create mode 100644 crates/goose-provider-types/tests/prefix_invariance.rs

diff --git a/crates/goose-cli/src/commands/term.rs b/crates/goose-cli/src/commands/term.rs
index 9c80fc1e0e..41a39ee22c 100644
--- a/crates/goose-cli/src/commands/term.rs
+++ b/crates/goose-cli/src/commands/term.rs
@@ -248,6 +248,20 @@ pub async fn handle_term_log(command: String) -> Result<()> {
     Ok(())
 }
 
+fn shell_history_text(newest_first_tail: &[&Message]) -> Option<String> {
+    let history: Vec<String> = newest_first_tail
+        .iter()
+        .filter(|m| !m.is_turn_context())
+        .rev()
+        .map(|m| m.as_concat_text())
+        .collect();
+    if history.is_empty() {
+        None
+    } else {
+        Some(history.join("\n"))
+    }
+}
+
 pub async fn handle_term_run(prompt: Vec<String>) -> Result<()> {
     let prompt = prompt.join(" ");
     let session_id = std::env::var("AGENT_SESSION_ID").map_err(|_| {
@@ -291,20 +305,12 @@ pub async fn handle_term_run(prompt: Vec<String>) -> Result<()> {
         }
     }
 
-    let prompt_with_context = if user_messages_after_last_assistant.is_empty() {
-        prompt
-    } else {
-        let history = user_messages_after_last_assistant
-            .iter()
-            .rev() // back to chronological order
-            .map(|m| m.as_concat_text())
-            .collect::<Vec<_>>()
-            .join("\n");
-
-        format!(
+    let prompt_with_context = match shell_history_text(&user_messages_after_last_assistant) {
+        Some(history) => format!(
             "<shell_history>\n{}\n</shell_history>\n\n{}",
             history, prompt
-        )
+        ),
+        None => prompt,
     };
 
     let config = SessionBuilderConfig {
@@ -407,4 +413,24 @@ mod tests {
 
         assert!(!script.contains("command_not_found"));
     }
+
+    #[test]
+    fn shell_history_skips_turn_context_events() {
+        use goose::conversation::message::MessageMetadata;
+
+        let older = Message::user().with_text("git status");
+        let block = Message::user()
+            .with_text("<turn-context>cwd /repo</turn-context>")
+            .with_metadata(MessageMetadata::agent_only().with_turn_context());
+        let newer = Message::user().with_text("cargo build");
+        let newest_first_tail = vec![&newer, &block, &older];
+
+        assert_eq!(
+            shell_history_text(&newest_first_tail).unwrap(),
+            "git status\ncargo build"
+        );
+
+        let only_block = vec![&block];
+        assert_eq!(shell_history_text(&only_block), None);
+    }
 }
diff --git a/crates/goose-cli/src/session/mod.rs b/crates/goose-cli/src/session/mod.rs
index 6ad4fe4861..87b1cd569c 100644
--- a/crates/goose-cli/src/session/mod.rs
+++ b/crates/goose-cli/src/session/mod.rs
@@ -12,7 +12,7 @@ mod thinking;
 use crate::session::task_execution_display::{
     format_task_execution_notification, TASK_EXECUTION_NOTIFICATION_TYPE,
 };
-use goose::conversation::{fix_conversation, Conversation};
+use goose::conversation::{fix_conversation, merge_consecutive_messages_for_request, Conversation};
 use std::env;
 use std::io::Write;
 use std::str::FromStr;
@@ -69,8 +69,16 @@ const SHELL_STATUS_MAX_LINES: usize = 3;
 const SHELL_STATUS_RESERVED_WIDTH: usize = 2;
 
 fn planner_provider_messages(plan_messages: &Conversation) -> Conversation {
-    let projected_messages = plan_messages.agent_visible_messages();
-    fix_conversation(Conversation::new_unvalidated(projected_messages)).0
+    // The planner prompt has no turn-context instructions; drop the blocks.
+    let projected_messages: Vec<Message> = plan_messages
+        .agent_visible_messages()
+        .into_iter()
+        .filter(|message| !message.is_turn_context())
+        .collect();
+    let fixed = fix_conversation(Conversation::new_unvalidated(projected_messages)).0;
+    Conversation::new_unvalidated(merge_consecutive_messages_for_request(
+        fixed.messages().clone(),
+    ))
 }
 
 #[derive(Serialize, Deserialize, Debug)]
@@ -1645,24 +1653,29 @@ impl CliSession {
                 &Message::assistant().with_text(interrupt_prompt),
                 self.debug,
             );
-        } else if let Some(last_msg) = self.messages.last() {
-            if last_msg.role == rmcp::model::Role::User {
-                match last_msg.content.first() {
-                    Some(MessageContent::ToolResponse(_)) => {
-                        self.push_message(Message::assistant().with_text(interrupt_prompt));
-                        output::render_message(
-                            &Message::assistant().with_text(interrupt_prompt),
-                            self.debug,
-                        );
-                    }
-                    Some(_) => {
-                        self.messages.pop();
-                        let assistant_msg = Message::assistant().with_text(interrupt_prompt);
-                        self.push_message(assistant_msg.clone());
-                        output::render_message(&assistant_msg, self.debug);
-                    }
-                    None => {
-                        // Empty message content — nothing to do, just continue gracefully
+        } else {
+            while self.messages.last().is_some_and(Message::is_turn_context) {
+                self.messages.pop();
+            }
+            if let Some(last_msg) = self.messages.last() {
+                if last_msg.role == rmcp::model::Role::User {
+                    match last_msg.content.first() {
+                        Some(MessageContent::ToolResponse(_)) => {
+                            self.push_message(Message::assistant().with_text(interrupt_prompt));
+                            output::render_message(
+                                &Message::assistant().with_text(interrupt_prompt),
+                                self.debug,
+                            );
+                        }
+                        Some(_) => {
+                            self.messages.pop();
+                            let assistant_msg = Message::assistant().with_text(interrupt_prompt);
+                            self.push_message(assistant_msg.clone());
+                            output::render_message(&assistant_msg, self.debug);
+                        }
+                        None => {
+                            // Empty message content — nothing to do, just continue gracefully
+                        }
                     }
                 }
             }
@@ -2646,6 +2659,32 @@ mod tests {
             .contains("hidden separator"));
     }
 
+    #[test]
+    fn planner_history_excludes_turn_context_events() {
+        use goose::conversation::message::MessageMetadata;
+
+        let history = Conversation::new_unvalidated([
+            Message::user().with_text("plan the refactor"),
+            Message::user()
+                .with_text("<turn-context>cwd /repo, todo: ship v2</turn-context>")
+                .with_metadata(MessageMetadata::agent_only().with_turn_context()),
+            Message::assistant().with_text("on it"),
+        ]);
+
+        let provider_text = planner_provider_messages(&history)
+            .agent_visible_messages()
+            .iter()
+            .map(|message| message.as_concat_text())
+            .collect::<Vec<_>>()
+            .join("\n");
+
+        assert!(provider_text.contains("plan the refactor"));
+        assert!(
+            !provider_text.contains("turn-context"),
+            "the planner prompt has no turn-context instructions, so blocks must not reach it"
+        );
+    }
+
     #[test]
     fn test_format_elapsed_time_under_60_seconds() {
         // Test sub-second duration
diff --git a/crates/goose-provider-types/src/cache_semantics.rs b/crates/goose-provider-types/src/cache_semantics.rs
new file mode 100644
index 0000000000..edbbda2c70
--- /dev/null
+++ b/crates/goose-provider-types/src/cache_semantics.rs
@@ -0,0 +1,203 @@
+//! Prompt-cache semantics declared per (provider, model), instead of implied
+//! by whichever format module a request flows through.
+
+use serde_json::{json, Value};
+
+use crate::formats::openai::is_openai_responses_model;
+
+#[derive(Debug, Clone, Copy, PartialEq, Eq)]
+pub enum CacheSemantics {
+    /// Caller places markers; reuse needs an exact match of the marked bytes.
+    ExplicitBreakpoints { max_breakpoints: usize },
+    /// The longest matching stored prefix is reused implicitly.
+    ImplicitTolerant,
+    /// Only extends a prompt reproduced byte-for-byte from the start.
+    ImplicitStrict,
+    /// No known prompt cache.
+    Uncached,
+}
+
+impl CacheSemantics {
+    /// Unknown pairs default to `ImplicitStrict`, which is safe for every
+    /// cache.
+    pub fn for_model(provider_name: &str, model_name: &str) -> Self {
+        match provider_name {
+            "anthropic" | "minimax" | "zai" | "kimi_code" => {
+                CacheSemantics::ExplicitBreakpoints { max_breakpoints: 4 }
+            }
+            "aws_bedrock" | "databricks" | "gcp_vertex_ai" if model_name.contains("claude") => {
+                CacheSemantics::ExplicitBreakpoints { max_breakpoints: 4 }
+            }
+            "openrouter" | "litellm" if model_name.starts_with("anthropic/") => {
+                CacheSemantics::ExplicitBreakpoints { max_breakpoints: 4 }
+            }
+            "openai" | "azure_openai" | "github_copilot" => {
+                if is_openai_responses_model(model_name) {
+                    CacheSemantics::ImplicitStrict
+                } else {
+                    CacheSemantics::ImplicitTolerant
+                }
+            }
+            "moonshot" | "custom_deepseek" | "groq" | "together" | "fireworks-ai" | "mistral"
+            | "zhipu" | "alibaba" => CacheSemantics::ImplicitTolerant,
+            "snowflake" | "sagemaker_tgi" => CacheSemantics::Uncached,
+            _ => CacheSemantics::ImplicitStrict,
+        }
+    }
+
+    pub fn uses_explicit_breakpoints(self) -> bool {
+        matches!(self, CacheSemantics::ExplicitBreakpoints { .. })
+    }
+}
+
+/// Anthropic-dialect breakpoints for OpenAI-style chat payloads (OpenRouter,
+/// LiteLLM, Databricks).
+pub fn apply_chat_payload_breakpoints(payload: &mut Value) {
+    if let Some(messages) = payload
+        .get_mut("messages")
+        .and_then(|messages| messages.as_array_mut())
+    {
+        let mut user_count = 0;
+        for message in messages.iter_mut().rev() {
+            if message.get("role") != Some(&json!("user")) {
+                continue;
+            }
+            if mark_last_content_block(message) {
+                user_count += 1;
+                if user_count >= 2 {
+                    break;
+                }
+            }
+        }
+
+        if let Some(system_message) = messages
+            .iter_mut()
+            .find(|message| message.get("role") == Some(&json!("system")))
+        {
+            mark_last_content_block(system_message);
+        }
+    }
+
+    if let Some(last_tool) = payload
+        .get_mut("tools")
+        .and_then(|tools| tools.as_array_mut())
+        .and_then(|tools| tools.last_mut())
+    {
+        if let Some(function) = last_tool.get_mut("function").and_then(Value::as_object_mut) {
+            function.insert("cache_control".to_string(), json!({ "type": "ephemeral" }));
+        }
+    }
+}
+
+fn mark_last_content_block(message: &mut Value) -> bool {
+    let Some(content) = message.get_mut("content") else {
+        return false;
+    };
+    if let Some(text) = content.as_str() {
+        *content = json!([{
+            "type": "text",
+            "text": text,
+            "cache_control": { "type": "ephemeral" }
+        }]);
+        return true;
+    }
+    if let Some(block) = content
+        .as_array_mut()
+        .and_then(|blocks| blocks.last_mut())
+        .and_then(Value::as_object_mut)
+    {
+        block.insert("cache_control".to_string(), json!({ "type": "ephemeral" }));
+        return true;
+    }
+    false
+}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+
+    #[test]
+    fn for_model_resolves_registered_identifiers_and_defaults_to_strict() {
+        let explicit = CacheSemantics::ExplicitBreakpoints { max_breakpoints: 4 };
+        for (provider, model, expected) in [
+            ("anthropic", "claude-sonnet-4-5", explicit),
+            ("kimi_code", "kimi-for-coding", explicit),
+            ("aws_bedrock", "anthropic.claude-sonnet-4-5", explicit),
+            ("minimax", "MiniMax-M2.5", explicit),
+            ("openrouter", "anthropic/claude-sonnet-4-5", explicit),
+            (
+                "openrouter",
+                "openai/gpt-5.2",
+                CacheSemantics::ImplicitStrict,
+            ),
+            ("openai", "gpt-5.2", CacheSemantics::ImplicitStrict),
+            ("openai", "gpt-4.1-mini", CacheSemantics::ImplicitTolerant),
+            ("snowflake", "llama-3.3-70b", CacheSemantics::Uncached),
+            (
+                "some_new_vendor",
+                "some-model",
+                CacheSemantics::ImplicitStrict,
+            ),
+        ] {
+            assert_eq!(
+                CacheSemantics::for_model(provider, model),
+                expected,
+                "{provider}/{model}"
+            );
+        }
+    }
+
+    #[test]
+    fn breakpoints_cover_system_tools_and_last_two_user_messages() {
+        let mut payload = json!({
+            "model": "anthropic/claude-sonnet-4-5",
+            "messages": [
+                {"role": "system", "content": "be careful"},
+                {"role": "user", "content": "first"},
+                {"role": "assistant", "content": "ok"},
+                {"role": "user", "content": "second"},
+                {"role": "assistant", "content": "ok"},
+                {"role": "user", "content": "third"}
+            ],
+            "tools": [
+                {"type": "function", "function": {"name": "a"}},
+                {"type": "function", "function": {"name": "b"}}
+            ]
+        });
+        apply_chat_payload_breakpoints(&mut payload);
+
+        let messages = payload["messages"].as_array().unwrap();
+        assert_eq!(
+            messages[0]["content"][0]["cache_control"]["type"],
+            "ephemeral"
+        );
+        assert!(messages[1]["content"].is_string(), "only last two users");
+        assert_eq!(
+            messages[3]["content"][0]["cache_control"]["type"],
+            "ephemeral"
+        );
+        assert_eq!(
+            messages[5]["content"][0]["cache_control"]["type"],
+            "ephemeral"
+        );
+        let tools = payload["tools"].as_array().unwrap();
+        assert!(tools[0]["function"].get("cache_control").is_none());
+        assert_eq!(tools[1]["function"]["cache_control"]["type"], "ephemeral");
+    }
+
+    #[test]
+    fn array_content_user_messages_get_a_breakpoint() {
+        let mut payload = json!({
+            "messages": [
+                {"role": "user", "content": [
+                    {"type": "text", "text": "look at this"},
+                    {"type": "image_url", "image_url": {"url": "data:image/png;base64,xyz"}}
+                ]}
+            ]
+        });
+        apply_chat_payload_breakpoints(&mut payload);
+        let blocks = payload["messages"][0]["content"].as_array().unwrap();
+        assert!(blocks[0].get("cache_control").is_none());
+        assert_eq!(blocks[1]["cache_control"]["type"], "ephemeral");
+    }
+}
diff --git a/crates/goose-provider-types/src/conversation.rs b/crates/goose-provider-types/src/conversation.rs
index 56e3cadbc4..53572b6ee9 100644
--- a/crates/goose-provider-types/src/conversation.rs
+++ b/crates/goose-provider-types/src/conversation.rs
@@ -518,14 +518,33 @@ fn fix_tool_calling(mut messages: Vec<Message>) -> (Vec<Message>, Vec<String>) {
     (messages, issues)
 }
 
+/// Never merges across visibility or turn-context boundaries, so the result
+/// is safe to persist.
 pub fn merge_consecutive_messages(messages: Vec<Message>) -> (Vec<Message>, Vec<String>) {
+    merge_consecutive(messages, false)
+}
+
+/// Merges regardless of visibility, for providers that require strict role
+/// alternation. Never persist the result.
+pub fn merge_consecutive_messages_for_request(messages: Vec<Message>) -> Vec<Message> {
+    merge_consecutive(messages, true).0
+}
+
+fn merge_consecutive(
+    messages: Vec<Message>,
+    across_visibility: bool,
+) -> (Vec<Message>, Vec<String>) {
     let mut issues = Vec::new();
     let mut merged_messages: Vec<Message> = Vec::new();
 
     for message in messages {
         if let Some(last) = merged_messages.last_mut() {
             let effective = effective_role(&message);
-            if effective_role(last) == effective {
+            if effective_role(last) == effective
+                && (across_visibility
+                    || (last.metadata.user_visible == message.metadata.user_visible
+                        && last.metadata.turn_context == message.metadata.turn_context))
+            {
                 last.content.extend(message.content);
                 issues.push(format!("Merged consecutive {} messages", effective));
                 continue;
@@ -613,12 +632,6 @@ pub const TURN_CONTEXT_TAG: &str = "turn-context";
 pub const CURRENT_TIME_TAG: &str = "current-time";
 pub const WORKING_DIRECTORY_TAG: &str = "working-directory";
 
-pub fn is_turn_context_text(text: &str) -> bool {
-    text.starts_with(&format!("<{TURN_CONTEXT_TAG}>\n<{CURRENT_TIME_TAG}>"))
-        && text.contains(&format!("</{CURRENT_TIME_TAG}>\n<{WORKING_DIRECTORY_TAG}>"))
-        && text.trim_end().ends_with(&format!("</{TURN_CONTEXT_TAG}>"))
-}
-
 #[derive(Debug, Clone, Copy, PartialEq, Eq)]
 pub enum EffectiveRole {
     User,
@@ -713,7 +726,9 @@ pub fn debug_conversation_fix(
 
 #[cfg(test)]
 mod tests {
-    use crate::conversation::message::{InferenceMetadata, Message, MessageContentBlock};
+    use crate::conversation::message::{
+        InferenceMetadata, Message, MessageContentBlock, MessageMetadata,
+    };
     use crate::conversation::{debug_conversation_fix, fix_conversation, Conversation};
     use rmcp::model::{CallToolRequestParams, Role};
     use rmcp::object;
@@ -846,6 +861,62 @@ mod tests {
         assert_eq!(fixed[0].content.len(), 2);
     }
 
+    #[test]
+    fn merge_does_not_cross_user_visibility() {
+        let visible = Message::user().with_text("what is in main.rs?");
+        let hidden = Message::user()
+            .with_text("<turn-context>frozen</turn-context>")
+            .with_visibility(false, true);
+
+        let (fixed, _) = fix_conversation(Conversation::new_unvalidated(vec![visible, hidden]));
+        assert_eq!(
+            fixed.messages().len(),
+            2,
+            "the persistable form keeps the agent-only event separate"
+        );
+        assert!(fixed.messages()[0].is_user_visible());
+        assert!(!fixed.messages()[1].is_user_visible());
+
+        let merged =
+            crate::conversation::merge_consecutive_messages_for_request(fixed.messages().clone());
+        assert_eq!(
+            merged.len(),
+            1,
+            "the request form merges to satisfy role alternation"
+        );
+        assert_eq!(merged[0].content.len(), 2);
+    }
+
+    #[test]
+    fn merge_does_not_erase_turn_context_marker() {
+        let preserved_prompt = Message::user()
+            .with_text("the preserved prompt")
+            .with_metadata(MessageMetadata::agent_only());
+        let carried_event = Message::user()
+            .with_text("<turn-context>frozen</turn-context>")
+            .with_metadata(MessageMetadata::agent_only().with_turn_context());
+
+        let (fixed, _) = fix_conversation(Conversation::new_unvalidated(vec![
+            preserved_prompt,
+            carried_event,
+        ]));
+        assert_eq!(
+            fixed.messages().len(),
+            2,
+            "the persistable form must not fold a turn-context event into the prompt"
+        );
+        assert!(!fixed.messages()[0].is_turn_context());
+        assert!(fixed.messages()[1].is_turn_context());
+
+        let merged =
+            crate::conversation::merge_consecutive_messages_for_request(fixed.messages().clone());
+        assert_eq!(
+            merged.len(),
+            1,
+            "the request form still merges to satisfy role alternation"
+        );
+    }
+
     #[test]
     fn test_orphaned_tools_and_empty_messages() {
         use rmcp::model::ContentBlock;
diff --git a/crates/goose-provider-types/src/conversation/message.rs b/crates/goose-provider-types/src/conversation/message.rs
index f158b9c605..65b0628109 100644
--- a/crates/goose-provider-types/src/conversation/message.rs
+++ b/crates/goose-provider-types/src/conversation/message.rs
@@ -742,6 +742,9 @@ pub struct MessageMetadata {
     /// without matching user-visible text. Never sent to providers.
     #[serde(default, skip_serializing_if = "std::ops::Not::not")]
     pub steer: bool,
+    /// Whether this message is a per-turn context event appended by the agent.
+    #[serde(default, skip_serializing_if = "std::ops::Not::not")]
+    pub turn_context: bool,
     #[serde(default, skip_serializing_if = "Option::is_none")]
     pub usage: Option<Box<MessageUsage>>,
     /// What an operation did to this message, keyed by operation name. Read back
@@ -759,6 +762,7 @@ impl Default for MessageMetadata {
             inference: None,
             output_token_limit_reached: false,
             steer: false,
+            turn_context: false,
             usage: None,
             operations: None,
         }
@@ -846,6 +850,11 @@ impl MessageMetadata {
         self.steer = true;
         self
     }
+
+    pub fn with_turn_context(mut self) -> Self {
+        self.turn_context = true;
+        self
+    }
 }
 
 #[derive(Clone, PartialEq, Serialize, Deserialize, Debug)]
@@ -1228,6 +1237,10 @@ impl Message {
     pub fn is_agent_visible(&self) -> bool {
         self.metadata.agent_visible
     }
+
+    pub fn is_turn_context(&self) -> bool {
+        self.metadata.turn_context
+    }
 }
 
 #[derive(Debug, Clone, Default, Serialize, Deserialize)]
diff --git a/crates/goose-provider-types/src/formats/anthropic.rs b/crates/goose-provider-types/src/formats/anthropic.rs
index c14b21db9e..0472dffff0 100644
--- a/crates/goose-provider-types/src/formats/anthropic.rs
+++ b/crates/goose-provider-types/src/formats/anthropic.rs
@@ -404,27 +404,16 @@ fn format_messages_with_options(
         }));
     }
 
-    // The volatile turn-context must sit after every cache breakpoint, or it invalidates the
-    // message-level cached prefix (Anthropic hashes tools -> system -> messages). Move it to the
-    // tail and place cache_control on the last non-turn-context block.
-    relocate_turn_context_to_tail(&mut anthropic_messages);
-
+    // The last two user messages extend the cached prefix each turn.
     let mut user_count = 0;
     for message in anthropic_messages.iter_mut().rev() {
         if message.get(ROLE_FIELD) != Some(&json!(USER_ROLE)) {
             continue;
         }
-        let Some(content_array) = message
+        if let Some(block) = message
             .get_mut(CONTENT_FIELD)
             .and_then(|content| content.as_array_mut())
-        else {
-            continue;
-        };
-        let Some(target) = cache_control_target_index(content_array) else {
-            continue;
-        };
-        if let Some(block) = content_array
-            .get_mut(target)
+            .and_then(|content_array| content_array.last_mut())
             .and_then(|b| b.as_object_mut())
         {
             block.insert(
@@ -441,52 +430,6 @@ fn format_messages_with_options(
     anthropic_messages
 }
 
-fn relocate_turn_context_to_tail(messages: &mut [Value]) {
-    let Some(last) = messages.len().checked_sub(1) else {
-        return;
-    };
-    let source = messages.iter().enumerate().rev().find_map(|(mi, m)| {
-        m.get(CONTENT_FIELD)
-            .and_then(|c| c.as_array())
-            .and_then(|a| a.iter().position(is_turn_context_block))
-            .map(|bi| (mi, bi))
-    });
-    let Some((mi, bi)) = source else {
-        return;
-    };
-    if mi != last
-        && messages[mi]
-            .get(CONTENT_FIELD)
-            .and_then(|c| c.as_array())
-            .map_or(0, |a| a.len())
-            <= 1
-    {
-        return;
-    }
-    let block = messages[mi][CONTENT_FIELD]
-        .as_array_mut()
-        .unwrap()
-        .remove(bi);
-    messages[last][CONTENT_FIELD]
-        .as_array_mut()
-        .unwrap()
-        .push(block);
-}
-
-fn cache_control_target_index(content_array: &[Value]) -> Option<usize> {
-    content_array
-        .iter()
-        .rposition(|block| !is_turn_context_block(block))
-}
-
-fn is_turn_context_block(block: &Value) -> bool {
-    block.get(TYPE_FIELD).and_then(Value::as_str) == Some(TEXT_TYPE)
-        && block
-            .get(TEXT_TYPE)
-            .and_then(Value::as_str)
-            .is_some_and(crate::conversation::is_turn_context_text)
-}
-
 fn anthropic_flavored_input_schema(input_schema: Arc<JsonObject>) -> Arc<JsonObject> {
     if input_schema.is_empty() {
         return Arc::new(json_object!({
@@ -2543,29 +2486,12 @@ mod tests {
         assert!(parts.tool_errors.is_empty());
     }
 
-    /// Anthropic prefix caching only pays off when the bytes up to a cache
-    /// breakpoint are identical turn over turn. The per-turn turn-context block
-    /// (timestamp, turn budget, compaction state) changes on every call, so if
-    /// it ever lands inside a cached prefix every request becomes a cache write
-    /// instead of a read. These tests pin the property that keeps caching alive
-    /// so a future refactor of the formatter or the turn-context format can't
-    /// silently regress it.
-    mod cache_prefix_stability {
+    /// Placement shape only; cross-request prefix stability is covered by
+    /// `tests/prefix_invariance.rs`.
+    mod cache_breakpoint_placement {
         use super::*;
         use rmcp::model::CallToolResult;
 
-        /// A turn-context block whose shape matches what `is_turn_context_text`
-        /// recognizes, varying only the volatile fields.
-        fn turn_context(time: &str, turn_budget: &str) -> String {
-            format!(
-                "<turn-context>\n\
-                 <current-time>{time}</current-time>\n\
-                 <working-directory>/Users/me/code/goose</working-directory>\n\
-                 <turn-budget>{turn_budget}</turn-budget>\n\
-                 </turn-context>"
-            )
-        }
-
         fn sample_tools() -> Vec<Tool> {
             vec![
                 Tool::new(
@@ -2587,11 +2513,21 @@ mod tests {
             ]
         }
 
-        /// A realistic multi-turn conversation. `inject_moim` prepends the
-        /// turn-context block to the latest genuine user message, so it sits as
-        /// the first text block of the final user message here.
-        fn conversation(turn_context_block: &str) -> Vec<Message> {
-            vec![
+        fn breakpoints(messages: &[Value]) -> Vec<(usize, usize)> {
+            let mut found = Vec::new();
+            for (mi, message) in messages.iter().enumerate() {
+                for (bi, block) in message["content"].as_array().unwrap().iter().enumerate() {
+                    if block.get(CACHE_CONTROL_FIELD).is_some() {
+                        found.push((mi, bi));
+                    }
+                }
+            }
+            found
+        }
+
+        #[test]
+        fn breakpoints_cover_tools_system_and_last_two_user_messages() {
+            let messages = vec![
                 Message::user().with_text("What does the main entrypoint do?"),
                 Message::assistant().with_tool_request(
                     "tool_1",
@@ -2605,200 +2541,45 @@ mod tests {
                     ])),
                 ),
                 Message::assistant().with_text("It calls `run()`."),
-                Message::user()
-                    .with_text(turn_context_block)
-                    .with_text("Now add error handling to it."),
-            ]
-        }
-
-        /// The (message index, block index) of the last block carrying a
-        /// `cache_control` marker, scanning in canonical order. This is the far
-        /// edge of the furthest cached prefix.
-        fn last_breakpoint(messages: &[Value]) -> Option<(usize, usize)> {
-            let mut found = None;
-            for (mi, message) in messages.iter().enumerate() {
-                for (bi, block) in message["content"].as_array().unwrap().iter().enumerate() {
-                    if block.get(CACHE_CONTROL_FIELD).is_some() {
-                        found = Some((mi, bi));
-                    }
-                }
-            }
-            found
-        }
-
-        fn find_turn_context(messages: &[Value]) -> Option<(usize, usize)> {
-            messages.iter().enumerate().find_map(|(mi, message)| {
-                message["content"]
-                    .as_array()
-                    .unwrap()
-                    .iter()
-                    .position(is_turn_context_block)
-                    .map(|bi| (mi, bi))
-            })
-        }
-
-        /// The exact bytes Anthropic hashes for its furthest cache breakpoint:
-        /// tools, then system, then messages truncated at the last
-        /// `cache_control` marker. Everything after that point is outside every
-        /// cached prefix and may change freely turn to turn.
-        fn cached_prefix(payload: &Value) -> String {
-            let messages = payload["messages"].as_array().unwrap();
-            let (last_mi, last_bi) = last_breakpoint(messages)
-                .expect("request must carry at least one cache_control breakpoint");
-
-            let prefix_messages: Vec<Value> = messages
-                .iter()
-                .take(last_mi + 1)
-                .enumerate()
-                .map(|(mi, message)| {
-                    let mut message = message.clone();
-                    if mi == last_mi {
-                        message["content"]
-                            .as_array_mut()
-                            .unwrap()
-                            .truncate(last_bi + 1);
-                    }
-                    message
-                })
-                .collect();
-
-            json!({
-                "tools": payload.get("tools"),
-                "system": payload.get("system"),
-                "messages": prefix_messages,
-            })
-            .to_string()
-        }
-
-        /// The production tool-loop case: `inject_moim` prepends turn-context to
-        /// the latest *genuine* user message, but the request then ends with a
-        /// later `tool_result` message. The block must be relocated *across*
-        /// messages to land after the trailing breakpoint, not merely reordered
-        /// within its own message.
-        fn tool_loop_conversation(turn_context_block: &str) -> Vec<Message> {
-            vec![
-                Message::user().with_text("What does the main entrypoint do?"),
-                Message::assistant().with_text("Let me read it."),
-                Message::user()
-                    .with_text(turn_context_block)
-                    .with_text("Now add error handling to it."),
-                Message::assistant().with_tool_request(
-                    "tool_1",
-                    Ok(CallToolRequestParams::new("read_file")
-                        .with_arguments(object!({"path": "src/main.rs"}))),
-                ),
-                Message::user().with_tool_response(
-                    "tool_1",
-                    Ok(CallToolResult::success(vec![
-                        rmcp::model::ContentBlock::text("fn main() { run(); }"),
-                    ])),
-                ),
-            ]
-        }
-
-        fn request_with(messages: &[Message]) -> Value {
-            create_request_with_default_options(
+                Message::user().with_text("Now add error handling to it."),
+            ];
+            let req = create_request_with_default_options(
                 &cfg("claude-sonnet-4-5"),
                 "You are a careful coding assistant.",
-                messages,
+                &messages,
                 &sample_tools(),
             )
-            .unwrap()
-        }
+            .unwrap();
 
-        fn request(turn_context_block: &str) -> Value {
-            request_with(&conversation(turn_context_block))
-        }
-
-        #[test]
-        fn cached_prefix_is_invariant_to_turn_context_changes() {
-            let req_a = request(&turn_context("2026-06-25 12:00:00", "14/40 used"));
-            let req_b = request(&turn_context("2026-06-25 13:47:00", "31/40 used"));
-
-            assert_ne!(
-                req_a.to_string(),
-                req_b.to_string(),
-                "test setup is vacuous: the two requests are byte-identical, so the \
-                 turn-context never reached the request body"
-            );
+            let tools = req["tools"].as_array().unwrap();
+            assert!(tools[0].get(CACHE_CONTROL_FIELD).is_none());
+            assert!(tools[1].get(CACHE_CONTROL_FIELD).is_some());
+            assert!(req["system"][0].get(CACHE_CONTROL_FIELD).is_some());
 
+            let request_messages = req["messages"].as_array().unwrap();
+            let marked = breakpoints(request_messages);
             assert_eq!(
-                cached_prefix(&req_a),
-                cached_prefix(&req_b),
-                "the cached prefix changed when only the volatile turn-context changed; \
-                 prefix caching will collapse into a per-turn cache write"
-            );
-
-            assert!(
-                !cached_prefix(&req_a).contains("12:00:00"),
-                "the volatile turn-context timestamp leaked into the cached prefix"
+                marked,
+                vec![(2, 0), (4, 0)],
+                "message breakpoints should sit on the last block of the last two user messages"
             );
         }
 
         #[test]
-        fn turn_context_sits_after_every_cache_breakpoint() {
-            let req = request(&turn_context("2026-06-25 12:00:00", "14/40 used"));
-            let messages = req["messages"].as_array().unwrap();
+        fn breakpoints_land_on_the_last_content_block() {
+            let messages = vec![Message::user()
+                .with_text("Here is the context.")
+                .with_text("And the question.")];
+            let req = create_request_with_default_options(
+                &cfg("claude-sonnet-4-5"),
+                "You are a careful coding assistant.",
+                &messages,
+                &sample_tools(),
+            )
+            .unwrap();
 
-            for message in messages {
-                for block in message["content"].as_array().unwrap() {
-                    if block.get(CACHE_CONTROL_FIELD).is_some() {
-                        assert!(
-                            !is_turn_context_block(block),
-                            "a cache_control breakpoint landed on the volatile turn-context block"
-                        );
-                    }
-                }
-            }
-
-            let breakpoint = last_breakpoint(messages).expect("a breakpoint should exist");
-            let turn_context = find_turn_context(messages)
-                .expect("the turn-context block should survive into the formatted request");
-            assert!(
-                turn_context > breakpoint,
-                "turn-context at {turn_context:?} is not after the last cache breakpoint at \
-                 {breakpoint:?}, so it sits inside a cached prefix"
-            );
-        }
-
-        /// Guards the tool-loop path: turn-context is injected onto an earlier
-        /// genuine user message while the request ends with a `tool_result`, so
-        /// keeping it out of the cached prefix requires relocating it across
-        /// messages. A regression that only reorders within a message would
-        /// pass the tests above but fail here.
-        #[test]
-        fn cached_prefix_is_invariant_in_tool_loop() {
-            let req_a = request_with(&tool_loop_conversation(&turn_context(
-                "2026-06-25 12:00:00",
-                "14/40",
-            )));
-            let req_b = request_with(&tool_loop_conversation(&turn_context(
-                "2026-06-25 13:47:00",
-                "31/40",
-            )));
-
-            assert_ne!(
-                req_a.to_string(),
-                req_b.to_string(),
-                "test setup is vacuous: turn-context never reached the request body"
-            );
-
-            assert_eq!(
-                cached_prefix(&req_a),
-                cached_prefix(&req_b),
-                "the cached prefix changed when only the volatile turn-context changed during a \
-                 tool loop; the block was not relocated past the trailing tool_result breakpoint"
-            );
-
-            let messages = req_a["messages"].as_array().unwrap();
-            let breakpoint = last_breakpoint(messages).expect("a breakpoint should exist");
-            let turn_context = find_turn_context(messages)
-                .expect("the turn-context block should survive into the formatted request");
-            assert!(
-                turn_context > breakpoint,
-                "turn-context at {turn_context:?} was not relocated across messages to after the \
-                 last breakpoint at {breakpoint:?}"
-            );
+            let request_messages = req["messages"].as_array().unwrap();
+            assert_eq!(breakpoints(request_messages), vec![(0, 1)]);
         }
     }
 }
diff --git a/crates/goose-provider-types/src/formats/databricks.rs b/crates/goose-provider-types/src/formats/databricks.rs
index 3eccc400c9..236ed1d2a8 100644
--- a/crates/goose-provider-types/src/formats/databricks.rs
+++ b/crates/goose-provider-types/src/formats/databricks.rs
@@ -1,3 +1,4 @@
+use crate::cache_semantics::{apply_chat_payload_breakpoints, CacheSemantics};
 use crate::conversation::message::{Message, MessageContentBlock};
 use crate::formats::anthropic::{
     adaptive_output_effort, model_supports_temperature, thinking_budget_tokens,
@@ -475,87 +476,6 @@ fn is_claude_model(model_name: &str) -> bool {
     model_name.contains("claude")
 }
 
-/// Add Anthropic-style cache_control fields to the request payload for Claude models.
-/// This enables prompt caching to reduce costs when using Claude via Databricks.
-///
-/// Cache control is added to:
-/// - The system message
-/// - The last two user messages (for incremental caching across turns)
-/// - The last tool definition (so all tools are cached as a single prefix)
-pub fn apply_cache_control_for_claude(payload: &mut Value) {
-    if let Some(messages_spec) = payload
-        .as_object_mut()
-        .and_then(|obj| obj.get_mut("messages"))
-        .and_then(|messages| messages.as_array_mut())
-    {
-        // Add cache_control to the last two user messages for incremental caching.
-        // The last message gets cached so future turns can read from it.
-        // The second-to-last user message is also cached to read from the previous cache.
-        let mut user_count = 0;
-        for message in messages_spec.iter_mut().rev() {
-            if message.get("role") == Some(&json!("user")) {
-                if let Some(content) = message.get_mut("content") {
-                    if let Some(content_str) = content.as_str() {
-                        *content = json!([{
-                            "type": "text",
-                            "text": content_str,
-                            "cache_control": { "type": "ephemeral" }
-                        }]);
-                    } else if let Some(content_array) = content.as_array_mut() {
-                        // Content is already an array, add cache_control to the last element
-                        if let Some(last_content) = content_array.last_mut() {
-                            if let Some(obj) = last_content.as_object_mut() {
-                                obj.insert(
-                                    "cache_control".to_string(),
-                                    json!({ "type": "ephemeral" }),
-                                );
-                            }
-                        }
-                    }
-                }
-                user_count += 1;
-                if user_count >= 2 {
-                    break;
-                }
-            }
-        }
-
-        // Add cache_control to the system message
-        if let Some(system_message) = messages_spec
-            .iter_mut()
-            .find(|msg| msg.get("role") == Some(&json!("system")))
-        {
-            if let Some(content) = system_message.get_mut("content") {
-                if let Some(content_str) = content.as_str() {
-                    *system_message = json!({
-                        "role": "system",
-                        "content": [{
-                            "type": "text",
-                            "text": content_str,
-                            "cache_control": { "type": "ephemeral" }
-                        }]
-                    });
-                }
-            }
-        }
-    }
-
-    // Add cache_control to the last tool definition
-    if let Some(tools_spec) = payload
-        .as_object_mut()
-        .and_then(|obj| obj.get_mut("tools"))
-        .and_then(|tools| tools.as_array_mut())
-    {
-        if let Some(last_tool) = tools_spec.last_mut() {
-            if let Some(function) = last_tool.get_mut("function") {
-                if let Some(obj) = function.as_object_mut() {
-                    obj.insert("cache_control".to_string(), json!({ "type": "ephemeral" }));
-                }
-            }
-        }
-    }
-}
-
 #[allow(clippy::too_many_lines)]
 pub fn create_request(
     model_config: &ModelConfig,
@@ -658,9 +578,9 @@ pub fn create_request_for_provider(
         );
     }
 
-    // Apply cache control for Claude models to enable prompt caching
-    if is_claude_model(&model_config.model_name) {
-        apply_cache_control_for_claude(&mut payload);
+    if CacheSemantics::for_model("databricks", &model_config.model_name).uses_explicit_breakpoints()
+    {
+        apply_chat_payload_breakpoints(&mut payload);
     }
 
     // Add request_params to the payload (e.g., anthropic_beta for extended context)
@@ -1534,138 +1454,6 @@ mod tests {
         assert!(!is_claude_model("databricks-meta-llama-3-3-70b"));
     }
 
-    #[test]
-    fn test_apply_cache_control_for_claude_system_message() -> anyhow::Result<()> {
-        let mut payload = json!({
-            "model": "databricks-claude-sonnet-4",
-            "messages": [
-                {
-                    "role": "system",
-                    "content": "You are a helpful assistant."
-                },
-                {
-                    "role": "user",
-                    "content": "Hello"
-                }
-            ]
-        });
-
-        apply_cache_control_for_claude(&mut payload);
-
-        let messages = payload["messages"].as_array().unwrap();
-        let system_msg = &messages[0];
-
-        // System message content should be converted to array with cache_control
-        assert!(system_msg["content"].is_array());
-        let content = system_msg["content"].as_array().unwrap();
-        assert_eq!(content.len(), 1);
-        assert_eq!(content[0]["type"], "text");
-        assert_eq!(content[0]["text"], "You are a helpful assistant.");
-        assert_eq!(content[0]["cache_control"]["type"], "ephemeral");
-
-        Ok(())
-    }
-
-    #[test]
-    fn test_apply_cache_control_for_claude_user_messages() -> anyhow::Result<()> {
-        let mut payload = json!({
-            "model": "databricks-claude-sonnet-4",
-            "messages": [
-                {
-                    "role": "system",
-                    "content": "You are helpful"
-                },
-                {
-                    "role": "user",
-                    "content": "First question"
-                },
-                {
-                    "role": "assistant",
-                    "content": "First answer"
-                },
-                {
-                    "role": "user",
-                    "content": "Second question"
-                },
-                {
-                    "role": "assistant",
-                    "content": "Second answer"
-                },
-                {
-                    "role": "user",
-                    "content": "Third question"
-                }
-            ]
-        });
-
-        apply_cache_control_for_claude(&mut payload);
-
-        let messages = payload["messages"].as_array().unwrap();
-
-        // First user message should NOT have cache_control (only last 2)
-        let first_user = &messages[1];
-        assert_eq!(first_user["content"], "First question");
-
-        // Second-to-last user message should have cache_control
-        let second_user = &messages[3];
-        assert!(second_user["content"].is_array());
-        assert_eq!(
-            second_user["content"][0]["cache_control"]["type"],
-            "ephemeral"
-        );
-
-        // Last user message should have cache_control
-        let last_user = &messages[5];
-        assert!(last_user["content"].is_array());
-        assert_eq!(
-            last_user["content"][0]["cache_control"]["type"],
-            "ephemeral"
-        );
-
-        Ok(())
-    }
-
-    #[test]
-    fn test_apply_cache_control_for_claude_tools() -> anyhow::Result<()> {
-        let mut payload = json!({
-            "model": "databricks-claude-sonnet-4",
-            "messages": [
-                {
-                    "role": "system",
-                    "content": "You are helpful"
-                }
-            ],
-            "tools": [
-                {
-                    "type": "function",
-                    "function": {
-                        "name": "tool1",
-                        "description": "First tool"
-                    }
-                },
-                {
-                    "type": "function",
-                    "function": {
-                        "name": "tool2",
-                        "description": "Second tool"
-                    }
-                }
-            ]
-        });
-
-        apply_cache_control_for_claude(&mut payload);
-
-        let tools = payload["tools"].as_array().unwrap();
-
-        // First tool should NOT have cache_control
-        assert!(tools[0]["function"].get("cache_control").is_none());
-
-        // Last tool should have cache_control
-        assert_eq!(tools[1]["function"]["cache_control"]["type"], "ephemeral");
-
-        Ok(())
-    }
-
     #[test]
     fn test_format_messages_with_thought_signature_metadata() -> anyhow::Result<()> {
         let mut metadata = serde_json::Map::new();
diff --git a/crates/goose-provider-types/src/formats/openai.rs b/crates/goose-provider-types/src/formats/openai.rs
index 52760a043b..2f24a0d2a4 100644
--- a/crates/goose-provider-types/src/formats/openai.rs
+++ b/crates/goose-provider-types/src/formats/openai.rs
@@ -67,10 +67,6 @@ pub fn is_reserved_request_param_key(key: &str) -> bool {
 pub struct OpenAiFormatOptions {
     pub preserve_thinking_context: bool,
     pub thinking_preservation_format: Option<ThinkingPreservationFormat>,
-    /// Keep the turn-context block on its source user message. The implicit
-    /// cache behind OpenAI's Responses-stack models only extends append-only
-    /// prompts, so the relocated tail would cap hits at the static prefix.
-    pub turn_context_in_place: bool,
 }
 
 fn merge_reasoning_text(prefix: &str, suffix: &str) -> String {
@@ -213,15 +209,6 @@ pub fn format_messages_with_options(
     image_format: &ImageFormat,
     options: OpenAiFormatOptions,
 ) -> Vec<Value> {
-    let extracted = if options.turn_context_in_place {
-        None
-    } else {
-        extract_turn_context(messages)
-    };
-    let (messages, turn_context) = match &extracted {
-        Some((stripped, text)) => (stripped.as_slice(), Some(text.as_str())),
-        None => (messages, None),
-    };
     let mut messages_spec = Vec::new();
     let mut pending_assistant_reasoning = String::new();
     // Reasoning to propagate across consecutive tool-call messages in the same turn.
@@ -531,60 +518,9 @@ pub fn format_messages_with_options(
         inline_reasoning_content(&mut messages_spec, format);
     }
 
-    if let Some(text) = turn_context {
-        append_turn_context_tail(&mut messages_spec, text);
-    }
-
     messages_spec
 }
 
-/// The volatile turn-context block busts implicit prefix caching from
-/// mid-history; re-emitted at the request tail instead. Mirrors formats/anthropic.rs.
-fn extract_turn_context(messages: &[Message]) -> Option<(Vec<Message>, String)> {
-    let (mi, bi) = messages.iter().enumerate().rev().find_map(|(mi, m)| {
-        if m.role != Role::User {
-            return None;
-        }
-        m.content
-            .iter()
-            .position(|block| {
-                matches!(block, MessageContentBlock::Text(t)
-                    if crate::conversation::is_turn_context_text(&t.text))
-            })
-            .map(|bi| (mi, bi))
-    })?;
-    if mi + 1 != messages.len() && messages[mi].content.len() <= 1 {
-        return None;
-    }
-    let mut messages = messages.to_vec();
-    let MessageContentBlock::Text(text) = messages[mi].content.remove(bi) else {
-        return None;
-    };
-    Some((messages, text.text))
-}
-
-/// Merges into a trailing user message when one exists; strict chat templates
-/// reject consecutive user messages.
-fn append_turn_context_tail(messages_spec: &mut Vec<Value>, text: &str) {
-    if let Some(last) = messages_spec.last_mut() {
-        if last["role"] == json!("user") {
-            match last.get_mut("content") {
-                Some(Value::String(existing)) => {
-                    existing.push('\n');
-                    existing.push_str(text);
-                    return;
-                }
-                Some(Value::Array(blocks)) => {
-                    blocks.push(json!({"type": "text", "text": text}));
-                    return;
-                }
-                _ => {}
-            }
-        }
-    }
-    messages_spec.push(json!({"role": "user", "content": text}));
-}
-
 /// Rewrites `reasoning_content` into the message `content` for models that reject a
 /// separate reasoning field on replay.
 ///
@@ -1628,8 +1564,6 @@ pub fn create_request_for_model_with_options(
         "content": system
     });
 
-    let mut format_options = format_options;
-    format_options.turn_context_in_place |= is_reasoning_model;
     let messages_spec = format_messages_with_options(messages, image_format, format_options);
     let mut tools_spec = format_tools(tools)?;
 
@@ -4849,7 +4783,6 @@ data: [DONE]"#;
             OpenAiFormatOptions {
                 preserve_thinking_context: true,
                 thinking_preservation_format: Some(format),
-                ..Default::default()
             },
         )
     }
@@ -4965,8 +4898,8 @@ data: [DONE]"#;
                 Message::user().with_text("What does the main entrypoint do?"),
                 Message::assistant().with_text("Let me read it."),
                 Message::user()
-                    .with_text(turn_context_block)
-                    .with_text("Now add error handling to it."),
+                    .with_text("Now add error handling to it.")
+                    .with_text(turn_context_block),
                 Message::assistant().with_tool_request(
                     "tool_1",
                     Ok(CallToolRequestParams::new("read_file")
@@ -4981,182 +4914,26 @@ data: [DONE]"#;
             ]
         }
 
-        fn prefix(spec: &[Value]) -> String {
-            json!(spec[..spec.len() - 1]).to_string()
-        }
-
         #[test]
-        fn formatted_prefix_is_invariant_to_turn_context_changes() {
-            let spec_a = format_messages(
-                &tool_loop_conversation(&turn_context("2026-08-03 12:00:00", "14/40 used")),
-                &ImageFormat::OpenAi,
-            );
-            let spec_b = format_messages(
-                &tool_loop_conversation(&turn_context("2026-08-03 13:47:00", "31/40 used")),
-                &ImageFormat::OpenAi,
-            );
-
-            assert_ne!(
-                json!(spec_a).to_string(),
-                json!(spec_b).to_string(),
-                "test setup is vacuous: the turn-context never reached the request body"
-            );
-            assert_eq!(
-                prefix(&spec_a),
-                prefix(&spec_b),
-                "the formatted prefix changed when only the volatile turn-context changed; \
-                 implicit prefix caching will re-prefill the conversation tail every request"
-            );
-        }
-
-        #[test]
-        fn turn_context_is_relocated_to_a_trailing_user_message() {
+        fn turn_context_stays_on_its_source_message() {
             let block = turn_context("2026-08-03 12:00:00", "14/40 used");
             let spec = format_messages(&tool_loop_conversation(&block), &ImageFormat::OpenAi);
 
-            let last = spec.last().unwrap();
-            assert_eq!(last["role"], "user");
-            assert_eq!(last["content"], json!(block));
-
-            let occurrences = spec
+            let occurrences: Vec<usize> = spec
                 .iter()
-                .filter(|m| {
+                .enumerate()
+                .filter_map(|(i, m)| {
                     m["content"]
                         .as_str()
                         .is_some_and(|c| c.contains("<turn-context>"))
+                        .then_some(i)
                 })
-                .count();
-            assert_eq!(occurrences, 1, "turn-context must appear exactly once");
-
+                .collect();
             assert_eq!(
-                spec[2]["content"],
-                json!("Now add error handling to it."),
-                "the source user message must keep its genuine text untouched"
+                occurrences,
+                vec![2],
+                "turn-context must appear exactly once, on its source message"
             );
         }
-
-        #[test]
-        fn first_request_of_a_turn_keeps_turn_context_inside_the_user_message() {
-            let block = turn_context("2026-08-03 12:00:00", "1/40 used");
-            let messages = vec![Message::user()
-                .with_text(&block)
-                .with_text("What does the main entrypoint do?")];
-            let spec = format_messages(&messages, &ImageFormat::OpenAi);
-
-            assert_eq!(spec.len(), 1);
-            assert_eq!(
-                spec[0]["content"],
-                json!(format!("What does the main entrypoint do?\n{block}"))
-            );
-        }
-
-        #[test]
-        fn mid_history_sole_turn_context_is_left_in_place() {
-            let block = turn_context("2026-08-03 12:00:00", "14/40 used");
-            let messages = vec![
-                Message::user().with_text(&block),
-                Message::assistant().with_text("Understood."),
-                Message::user().with_text("Please refactor the argument parser."),
-            ];
-            let spec = format_messages(&messages, &ImageFormat::OpenAi);
-
-            assert_eq!(spec.len(), 3);
-            assert_eq!(spec[0]["content"], json!(block));
-            assert_eq!(
-                spec[2]["content"],
-                json!("Please refactor the argument parser.")
-            );
-        }
-
-        #[test]
-        fn turn_context_merges_into_the_synthetic_image_message() {
-            let block = turn_context("2026-08-03 12:00:00", "14/40 used");
-            let mut messages = tool_loop_conversation(&block);
-            messages.pop();
-            messages.push(Message::user().with_tool_response(
-                "tool_1",
-                Ok(CallToolResult::success(vec![ContentBlock::image(
-                    "aGVsbG8=",
-                    "image/png",
-                )])),
-            ));
-            let spec = format_messages(&messages, &ImageFormat::OpenAi);
-
-            let last = spec.last().unwrap();
-            assert_eq!(last["role"], "user");
-            let blocks = last["content"].as_array().unwrap();
-            assert!(blocks.iter().any(|b| b["type"] == json!("image_url")));
-            assert_eq!(blocks.last().unwrap()["text"], json!(block));
-            for pair in spec.windows(2) {
-                assert!(
-                    !(pair[0]["role"] == json!("user") && pair[1]["role"] == json!("user")),
-                    "consecutive user messages reached the wire: {pair:?}"
-                );
-            }
-        }
-
-        fn responses_stack_request(messages: &[Message]) -> Vec<Value> {
-            let request = create_request(
-                &test_model_config("openai/gpt-5.6-terra"),
-                "system",
-                messages,
-                &[],
-                &ImageFormat::OpenAi,
-                false,
-            )
-            .unwrap();
-            request["messages"].as_array().unwrap().clone()
-        }
-
-        #[test]
-        fn responses_stack_tool_loop_requests_are_append_only() {
-            let block = turn_context("2026-08-03 12:00:00", "14/40 used");
-            let earlier = tool_loop_conversation(&block);
-            let mut later = earlier.clone();
-            later.push(
-                Message::assistant().with_tool_request(
-                    "tool_2",
-                    Ok(CallToolRequestParams::new("read_file")
-                        .with_arguments(object!({"path": "src/lib.rs"}))),
-                ),
-            );
-            later.push(Message::user().with_tool_response(
-                "tool_2",
-                Ok(CallToolResult::success(vec![ContentBlock::text(
-                    "pub fn run() {}",
-                )])),
-            ));
-
-            let spec_earlier = responses_stack_request(&earlier);
-            let spec_later = responses_stack_request(&later);
-
-            assert!(spec_later.len() > spec_earlier.len());
-            for (i, earlier_msg) in spec_earlier.iter().enumerate() {
-                assert_eq!(
-                    json!(earlier_msg).to_string(),
-                    json!(spec_later[i]).to_string(),
-                    "request N must be a byte prefix of request N+1 at index {i}"
-                );
-            }
-        }
-
-        #[test]
-        fn chat_stack_models_still_relocate_turn_context_to_the_tail() {
-            let block = turn_context("2026-08-03 12:00:00", "14/40 used");
-            let request = create_request(
-                &test_model_config("openai/gpt-4.1-mini"),
-                "system",
-                &tool_loop_conversation(&block),
-                &[],
-                &ImageFormat::OpenAi,
-                false,
-            )
-            .unwrap();
-            let spec = request["messages"].as_array().unwrap();
-
-            let last = spec.last().unwrap();
-            assert_eq!(last["role"], "user");
-            assert_eq!(last["content"], json!(block));
-        }
     }
 }
diff --git a/crates/goose-provider-types/src/lib.rs b/crates/goose-provider-types/src/lib.rs
index 3ab49ef87e..dd7a87dda7 100644
--- a/crates/goose-provider-types/src/lib.rs
+++ b/crates/goose-provider-types/src/lib.rs
@@ -1,4 +1,5 @@
 pub mod base;
+pub mod cache_semantics;
 pub mod canonical;
 pub mod conversation;
 pub mod errors;
diff --git a/crates/goose-provider-types/tests/prefix_invariance.rs b/crates/goose-provider-types/tests/prefix_invariance.rs
new file mode 100644
index 0000000000..5ec61e0eb6
--- /dev/null
+++ b/crates/goose-provider-types/tests/prefix_invariance.rs
@@ -0,0 +1,428 @@
+//! Across the consecutive requests of a session, the cache-relevant bytes a
+//! provider has already seen must never change.
+//!
+//! Implicit caches require request N to be a verbatim item-prefix of request
+//! N+1; explicit-breakpoint caches require the bytes up to the last
+//! breakpoint to recur at the same positions, modulo the markers themselves.
+//! Session states are shaped as the agent persists them and run through the
+//! same projection and `fix_conversation` pass as the real request path.
+
+use goose_provider_types::cache_semantics::{apply_chat_payload_breakpoints, CacheSemantics};
+use goose_provider_types::conversation::message::{Message, MessageMetadata};
+use goose_provider_types::conversation::{
+    fix_conversation, merge_consecutive_messages_for_request, Conversation,
+};
+use goose_provider_types::formats::anthropic::{self, AnthropicFormatOptions};
+use goose_provider_types::formats::{databricks, openai, openai_responses};
+use goose_provider_types::images::ImageFormat;
+use goose_provider_types::model::ModelConfig;
+use rmcp::model::{CallToolRequestParams, CallToolResult, ContentBlock, Tool};
+use rmcp::object;
+use serde_json::{json, Value};
+
+const SYSTEM: &str = "You are a careful coding assistant.";
+
+fn tools() -> Vec<Tool> {
+    vec![Tool::new(
+        "read_file",
+        "Read a file from disk",
+        object!({
+            "type": "object",
+            "properties": { "path": { "type": "string" } }
+        }),
+    )]
+}
+
+fn turn_block(turn: usize) -> String {
+    format!(
+        "<turn-context>\n\
+         <current-time>2026-08-06 12:0{turn}:00 +02:00</current-time>\n\
+         <working-directory>/Users/me/code/goose</working-directory>\n\
+         <todo>step {turn} of the plan</todo>\n\
+         </turn-context>"
+    )
+}
+
+fn turn_context_message(turn: usize) -> Message {
+    Message::user()
+        .with_text(turn_block(turn))
+        .with_metadata(MessageMetadata::agent_only().with_turn_context())
+}
+
+fn tool_exchange(id: &str, path: &str) -> [Message; 2] {
+    [
+        Message::assistant().with_tool_request(
+            id,
+            Ok(CallToolRequestParams::new("read_file").with_arguments(object!({ "path": path }))),
+        ),
+        Message::user().with_tool_response(
+            id,
+            Ok(CallToolResult::success(vec![ContentBlock::text(
+                "fn main() { run(); }",
+            )])),
+        ),
+    ]
+}
+
+/// Two turns with one tool-loop iteration each; every state appends to the
+/// previous one.
+fn session_states() -> Vec<Vec<Message>> {
+    let u1 = Message::user().with_text("What does the main entrypoint do?");
+    let u2 = Message::user().with_text("Now add error handling to it.");
+    let (tc1, tc2) = (turn_context_message(1), turn_context_message(2));
+    let [a1, t1] = tool_exchange("call_1", "src/main.rs");
+    let [a2, t2] = tool_exchange("call_2", "src/lib.rs");
+    let a_text = Message::assistant().with_text("It calls `run()`.");
+
+    vec![
+        vec![u1.clone(), tc1.clone()],
+        vec![u1.clone(), tc1.clone(), a1.clone(), t1.clone()],
+        vec![
+            u1.clone(),
+            tc1.clone(),
+            a1.clone(),
+            t1.clone(),
+            a_text.clone(),
+            u2.clone(),
+            tc2.clone(),
+        ],
+        vec![u1, tc1, a1, t1, a_text, u2, tc2, a2, t2],
+    ]
+}
+
+/// The projection every request goes through before any formatter
+/// (`stream_response_from_provider`).
+fn provider_view(messages: &[Message]) -> Vec<Message> {
+    let projected =
+        Conversation::new_unvalidated(messages.iter().cloned()).agent_visible_messages();
+    let (fixed, _) = fix_conversation(Conversation::new_unvalidated(projected));
+    merge_consecutive_messages_for_request(fixed.messages().clone())
+}
+
+fn anthropic_request(messages: &[Message]) -> Value {
+    anthropic::create_request(
+        "anthropic",
+        &ModelConfig::new("claude-sonnet-4-5"),
+        SYSTEM,
+        &provider_view(messages),
+        &tools(),
+        AnthropicFormatOptions::default(),
+    )
+    .unwrap()
+}
+
+fn openai_chat_messages(model: &str, messages: &[Message]) -> Vec<Value> {
+    openai::create_request(
+        &ModelConfig::new(model),
+        SYSTEM,
+        &provider_view(messages),
+        &tools(),
+        &ImageFormat::OpenAi,
+        false,
+    )
+    .unwrap()["messages"]
+        .as_array()
+        .unwrap()
+        .clone()
+}
+
+fn responses_input(messages: &[Message]) -> Vec<Value> {
+    openai_responses::create_responses_request(
+        &ModelConfig::new("gpt-5.2"),
+        SYSTEM,
+        &provider_view(messages),
+        &tools(),
+    )
+    .unwrap()["input"]
+        .as_array()
+        .unwrap()
+        .clone()
+}
+
+fn openrouter_style_request(messages: &[Message]) -> Value {
+    let mut payload = openai::create_request(
+        &ModelConfig::new("anthropic/claude-sonnet-4-5"),
+        SYSTEM,
+        &provider_view(messages),
+        &tools(),
+        &ImageFormat::OpenAi,
+        false,
+    )
+    .unwrap();
+    assert!(
+        CacheSemantics::for_model("openrouter", "anthropic/claude-sonnet-4-5")
+            .uses_explicit_breakpoints()
+    );
+    apply_chat_payload_breakpoints(&mut payload);
+    payload
+}
+
+fn databricks_request(messages: &[Message]) -> Value {
+    databricks::create_request(
+        &ModelConfig::new("databricks-claude-sonnet-4"),
+        SYSTEM,
+        &provider_view(messages),
+        &tools(),
+        &ImageFormat::OpenAi,
+    )
+    .unwrap()
+}
+
+/// Strip breakpoint markers and normalize string content to block form:
+/// upstream caches hash the normalized bytes, not the marker encoding.
+fn canonical(value: &Value) -> Value {
+    match value {
+        Value::Object(map) => Value::Object(
+            map.iter()
+                .filter(|(k, _)| k.as_str() != "cache_control")
+                .map(|(k, v)| {
+                    if k == "content" && v.is_string() {
+                        (
+                            k.clone(),
+                            json!([{ "type": "text", "text": v.as_str().unwrap() }]),
+                        )
+                    } else {
+                        (k.clone(), canonical(v))
+                    }
+                })
+                .collect(),
+        ),
+        Value::Array(items) => Value::Array(items.iter().map(canonical).collect()),
+        other => other.clone(),
+    }
+}
+
+fn strict_violations(prev: &[Value], next: &[Value]) -> Vec<String> {
+    if next.len() < prev.len() {
+        return vec![format!(
+            "request shrank from {} to {} items",
+            prev.len(),
+            next.len()
+        )];
+    }
+    prev.iter()
+        .zip(next)
+        .enumerate()
+        .filter(|(_, (p, n))| p != n)
+        .map(|(i, (p, n))| format!("items diverge at index {i}:\n  sent: {p}\n  next: {n}"))
+        .collect()
+}
+
+fn last_breakpoint(messages: &[Value]) -> Option<(usize, usize)> {
+    let mut found = None;
+    for (mi, message) in messages.iter().enumerate() {
+        let blocks = match message["content"].as_array() {
+            Some(blocks) => blocks.len(),
+            None => 1,
+        };
+        for bi in 0..blocks {
+            let block = match message["content"].as_array() {
+                Some(array) => &array[bi],
+                None => message,
+            };
+            if block.get("cache_control").is_some() {
+                found = Some((mi, bi));
+            }
+        }
+    }
+    found
+}
+
+/// Everything the previous request cached (tools, system, messages up to its
+/// last breakpoint) must recur verbatim in the next request.
+fn explicit_violations(prev_request: &Value, next_request: &Value) -> Vec<String> {
+    let mut violations = Vec::new();
+
+    let prev_messages = prev_request["messages"].as_array().unwrap();
+    let Some((last_mi, last_bi)) = last_breakpoint(prev_messages) else {
+        violations.push("previous request carries no message breakpoint".into());
+        return violations;
+    };
+
+    let prev = canonical(prev_request);
+    let next = canonical(next_request);
+    for section in ["tools", "system"] {
+        if prev[section] != next[section] {
+            violations.push(format!(
+                "cached section `{section}` changed between requests"
+            ));
+        }
+    }
+
+    let prev_messages = prev["messages"].as_array().unwrap();
+    let next_messages = next["messages"].as_array().unwrap();
+    if next_messages.len() <= last_mi {
+        violations.push("messages shrank below the previous breakpoint".into());
+        return violations;
+    }
+    for mi in 0..last_mi {
+        if prev_messages[mi] != next_messages[mi] {
+            violations.push(format!(
+                "cached bytes changed at message {mi}:\n  sent: {}\n  next: {}",
+                prev_messages[mi], next_messages[mi]
+            ));
+        }
+    }
+
+    let prev_blocks = prev_messages[last_mi]["content"].as_array().unwrap();
+    match next_messages[last_mi]["content"].as_array() {
+        Some(next_blocks)
+            if next_blocks.len() > last_bi
+                && prev_messages[last_mi]["role"] == next_messages[last_mi]["role"] =>
+        {
+            for bi in 0..=last_bi {
+                if prev_blocks[bi] != next_blocks[bi] {
+                    violations.push(format!(
+                        "cached bytes changed at message {last_mi} block {bi}:\n  sent: {}\n  next: {}",
+                        prev_blocks[bi], next_blocks[bi]
+                    ));
+                }
+            }
+        }
+        _ => violations.push(format!("cached message {last_mi} changed shape")),
+    }
+    violations
+}
+
+fn consecutive<T>(items: &[T]) -> impl Iterator<Item = (usize, &T, &T)> {
+    items.windows(2).enumerate().map(|(i, w)| (i, &w[0], &w[1]))
+}
+
+fn assert_clean(label: &str, violations: Vec<String>) {
+    assert!(
+        violations.is_empty(),
+        "{label}: cache-relevant bytes changed between consecutive requests:\n{}",
+        violations.join("\n")
+    );
+}
+
+#[test]
+fn anthropic_requests_stay_breakpoint_compatible() {
+    let requests: Vec<Value> = session_states()
+        .iter()
+        .map(|m| anthropic_request(m))
+        .collect();
+    assert_ne!(requests[0], requests[1], "vacuous: requests are identical");
+    for (i, prev, next) in consecutive(&requests) {
+        assert_clean(
+            &format!("anthropic pair {i}"),
+            explicit_violations(prev, next),
+        );
+    }
+}
+
+/// The chat fleet's caches are merely tolerant, but with no relocation left
+/// the strict relation holds anyway.
+#[test]
+fn openai_chat_requests_are_append_only() {
+    let requests: Vec<Vec<Value>> = session_states()
+        .iter()
+        .map(|m| openai_chat_messages("gpt-4.1-mini", m))
+        .collect();
+    for (i, prev, next) in consecutive(&requests) {
+        assert_clean(
+            &format!("openai chat pair {i}"),
+            strict_violations(prev, next),
+        );
+    }
+}
+
+#[test]
+fn responses_requests_are_append_only() {
+    let requests: Vec<Vec<Value>> = session_states()
+        .iter()
+        .map(|m| responses_input(m))
+        .collect();
+    for (i, prev, next) in consecutive(&requests) {
+        assert_clean(
+            &format!("responses pair {i}"),
+            strict_violations(prev, next),
+        );
+    }
+}
+
+#[test]
+fn responses_stack_chat_requests_are_append_only() {
+    let requests: Vec<Vec<Value>> = session_states()
+        .iter()
+        .map(|m| openai_chat_messages("gpt-5.6-terra", m))
+        .collect();
+    for (i, prev, next) in consecutive(&requests) {
+        assert_clean(
+            &format!("responses-stack chat pair {i}"),
+            strict_violations(prev, next),
+        );
+    }
+}
+
+/// The OpenRouter/LiteLLM path: an OpenAI chat payload post-processed with
+/// Anthropic-dialect breakpoints by the shared writer.
+#[test]
+fn openrouter_style_requests_stay_breakpoint_compatible() {
+    let requests: Vec<Value> = session_states()
+        .iter()
+        .map(|m| openrouter_style_request(m))
+        .collect();
+    for (i, prev, next) in consecutive(&requests) {
+        assert_clean(
+            &format!("openrouter pair {i}"),
+            explicit_violations(prev, next),
+        );
+    }
+}
+
+#[test]
+fn databricks_requests_stay_breakpoint_compatible() {
+    let requests: Vec<Value> = session_states()
+        .iter()
+        .map(|m| databricks_request(m))
+        .collect();
+    for (i, prev, next) in consecutive(&requests) {
+        assert_clean(
+            &format!("databricks pair {i}"),
+            explicit_violations(prev, next),
+        );
+    }
+}
+
+#[test]
+fn seeded_regression_volatile_bytes_in_cached_prefix_are_caught() {
+    let request_for = |stamp: &str| {
+        let block =
+            format!("<turn-context>\n<current-time>{stamp}</current-time>\n</turn-context>");
+        let [a1, t1] = tool_exchange("call_1", "src/main.rs");
+        anthropic_request(&[
+            Message::user()
+                .with_text(block)
+                .with_visibility(false, true),
+            Message::user().with_text("Now add error handling to it."),
+            a1,
+            t1,
+        ])
+    };
+    let violations = explicit_violations(
+        &request_for("2026-08-06 12:00:00"),
+        &request_for("2026-08-06 12:01:00"),
+    );
+    assert!(
+        !violations.is_empty(),
+        "expected per-request volatile bytes inside the cached prefix to be caught"
+    );
+}
+
+#[test]
+fn seeded_regression_relocated_tail_is_caught() {
+    let states = session_states();
+    let prev = responses_input(&states[0]);
+
+    let mut relocated_state = states[1].clone();
+    let block = relocated_state.remove(1);
+    relocated_state.push(block);
+    let next = responses_input(&relocated_state);
+
+    let violations = strict_violations(&prev, &next);
+    assert!(
+        !violations.is_empty(),
+        "expected a relocated turn-context block to violate the append-only relation"
+    );
+}
diff --git a/crates/goose-providers/src/lib.rs b/crates/goose-providers/src/lib.rs
index 7454264586..fb75fac7b9 100644
--- a/crates/goose-providers/src/lib.rs
+++ b/crates/goose-providers/src/lib.rs
@@ -6,8 +6,8 @@ pub mod databricks_auth;
 pub mod databricks_v2;
 pub mod google;
 pub use goose_provider_types::{
-    base, canonical, conversation, errors, formats, goose_mode, images, json, model, permission,
-    request_log, retry, thinking, utils,
+    base, cache_semantics, canonical, conversation, errors, formats, goose_mode, images, json,
+    model, permission, request_log, retry, thinking, utils,
 };
 pub mod declarative;
 pub mod http_status;
diff --git a/crates/goose-providers/src/openai.rs b/crates/goose-providers/src/openai.rs
index e8d03ccb83..b256ca989d 100644
--- a/crates/goose-providers/src/openai.rs
+++ b/crates/goose-providers/src/openai.rs
@@ -782,7 +782,6 @@ impl Provider for OpenAiProvider {
                     preserve_thinking_context: self.preserve_thinking_context
                         || thinking_preservation_format.is_some(),
                     thinking_preservation_format,
-                    ..Default::default()
                 },
             )?;
 
diff --git a/crates/goose/src/acp/provider.rs b/crates/goose/src/acp/provider.rs
index ec3d4e193d..f2b0b4e0dd 100644
--- a/crates/goose/src/acp/provider.rs
+++ b/crates/goose/src/acp/provider.rs
@@ -1442,14 +1442,14 @@ fn messages_to_prompt(messages: &[Message], include_handoff_context: bool) -> Ve
 fn last_user_message_index(messages: &[Message]) -> Option<usize> {
     messages
         .iter()
-        .rposition(|m| m.role == Role::User && m.is_agent_visible())
+        .rposition(|m| m.role == Role::User && m.is_agent_visible() && !m.is_turn_context())
 }
 
 fn has_handoff_context(messages: &[Message]) -> bool {
     last_user_message_index(messages).is_some_and(|last_user_index| {
         messages[..last_user_index]
             .iter()
-            .any(Message::is_agent_visible)
+            .any(|m| m.is_agent_visible() && !m.is_turn_context())
     })
 }
 
@@ -1458,6 +1458,7 @@ fn build_handoff_context_memo(prior_messages: &[Message]) -> Option<String> {
         Conversation::new_unvalidated(prior_messages.iter().cloned())
             .agent_visible_messages()
             .iter()
+            .filter(|message| !message.is_turn_context())
             .map(|message| format_message_for_compacting(&message.agent_visible_content()))
             .collect();
 
@@ -1810,6 +1811,37 @@ mod tests {
         assert_eq!(prompt_text(&blocks[1]), "continue from there");
     }
 
+    #[test]
+    fn messages_to_prompt_skips_turn_context_events() {
+        use crate::conversation::message::MessageMetadata;
+
+        let turn_context = |text: &str| {
+            Message::user()
+                .with_text(text)
+                .with_metadata(MessageMetadata::agent_only().with_turn_context())
+        };
+        let messages = vec![
+            Message::user().with_text("inspect src/lib.rs"),
+            turn_context("<turn-context>old cwd /repo</turn-context>"),
+            Message::assistant().with_text("I found the file"),
+            Message::user().with_text("continue from there"),
+            turn_context("<turn-context>new cwd /repo</turn-context>"),
+        ];
+
+        let blocks = messages_to_prompt(&messages, true);
+
+        assert_eq!(blocks.len(), 2);
+        assert!(
+            !prompt_text(&blocks[0]).contains("turn-context"),
+            "handoff memo must not include turn-context events"
+        );
+        assert_eq!(
+            prompt_text(&blocks[1]),
+            "continue from there",
+            "the current prompt must be the user's request, not a trailing turn-context event"
+        );
+    }
+
     #[test]
     fn messages_to_prompt_drops_user_only_acp_rows_from_handoff() {
         let user_only = TextContent::new("SECRET_USER_ONLY")
diff --git a/crates/goose/src/agents/agent.rs b/crates/goose/src/agents/agent.rs
index 0d877809bf..69591818d9 100644
--- a/crates/goose/src/agents/agent.rs
+++ b/crates/goose/src/agents/agent.rs
@@ -46,7 +46,9 @@ use crate::conversation::message::{
     ActionRequiredData, InferenceMetadata, Message, MessageContent, MessageUsage, ProviderMetadata,
     SystemNotificationType, ToolRequest,
 };
-use crate::conversation::{debug_conversation_fix, fix_conversation, Conversation};
+use crate::conversation::{
+    debug_conversation_fix, fix_conversation, merge_consecutive_messages_for_request, Conversation,
+};
 use crate::mcp_utils::ToolResult;
 use crate::permission::permission_inspector::PermissionInspector;
 use crate::permission::permission_judge::PermissionCheckResult;
@@ -150,7 +152,6 @@ pub struct ReplyContext {
     pub system_prompt: String,
     pub goose_mode: GooseMode,
     pub tool_call_cut_off: usize,
-    pub initial_messages: Vec<Message>,
     pub model_config: goose_providers::model::ModelConfig,
 }
 
@@ -787,8 +788,6 @@ impl Agent {
                 )
             );
         }
-        let initial_messages = conversation.messages().clone();
-
         let (tools, toolshim_tools, system_prompt, model_config) = self
             .prepare_tools_and_prompt(session_id, working_dir)
             .await?;
@@ -820,7 +819,6 @@ impl Agent {
             system_prompt,
             goose_mode,
             tool_call_cut_off,
-            initial_messages,
             model_config,
         })
     }
@@ -2154,7 +2152,6 @@ impl Agent {
             mut system_prompt,
             tool_call_cut_off,
             goose_mode,
-            initial_messages,
             model_config,
         } = context;
 
@@ -2264,7 +2261,27 @@ impl Agent {
             let turn_start_compaction_info =
                 super::moim::compute_compaction_info(&session_config.id, &self.extension_manager)
                     .await;
-            let turn_start_turns_taken = turns_taken;
+
+            if let Some(turn_context) = super::moim::turn_context_message(
+                &session_config.id,
+                &self.extension_manager,
+                turns_taken,
+                max_turns,
+                turn_start,
+                turn_start_compaction_info,
+            )
+            .await
+            {
+                persist_and_push_message_with_id(
+                    &session_manager,
+                    &session_config.id,
+                    &mut conversation,
+                    turn_context,
+                )
+                .await?;
+            }
+            // Snapshot after the turn-context append so a retry keeps the sent prefix.
+            let initial_messages = conversation.messages().clone();
 
             loop {
                 if is_token_cancelled(&cancel_token) {
@@ -2359,23 +2376,12 @@ impl Agent {
                     break;
                 }
 
-                let conversation_with_moim = super::moim::inject_moim(
-                    &session_config.id,
-                    conversation.clone(),
-                    &self.extension_manager,
-                    turn_start_turns_taken,
-                    max_turns,
-                    turn_start,
-                    turn_start_compaction_info.clone(),
-                )
-                .await;
-
                 let mut stream = crate::agents::reply_parts::stream_response_from_provider(
                     self.provider().await?,
                     model_config.clone(),
                     &session_config.id,
                     &system_prompt,
-                    conversation_with_moim.messages(),
+                    conversation.messages(),
                     &tools,
                     &toolshim_tools,
                 ).await?;
@@ -3734,7 +3740,7 @@ impl Agent {
             .filter(super::reply_parts::is_tool_visible_to_model)
             .collect();
 
-        messages = Conversation::new_unvalidated(messages.agent_visible_messages());
+        messages = Conversation::new_unvalidated(recipe_conversation_history(&messages));
         messages.push(Message::user().with_text(recipe_prompt));
 
         let (messages, issues) = fix_conversation(messages);
@@ -3743,6 +3749,9 @@ impl Agent {
                 .iter()
                 .for_each(|issue| tracing::warn!(recipe.conversation.issue = issue));
         }
+        let messages = Conversation::new_unvalidated(merge_consecutive_messages_for_request(
+            messages.messages().clone(),
+        ));
 
         tracing::debug!(
             "Added recipe prompt to messages, total messages: {}",
@@ -3908,6 +3917,15 @@ impl Agent {
     }
 }
 
+fn recipe_conversation_history(messages: &Conversation) -> Vec<Message> {
+    // The recipe prompt has no turn-context instructions; drop the blocks.
+    messages
+        .agent_visible_messages()
+        .into_iter()
+        .filter(|message| !message.is_turn_context())
+        .collect()
+}
+
 #[cfg(test)]
 mod tests {
     use super::*;
@@ -3923,6 +3941,25 @@ mod tests {
     use std::sync::atomic::{AtomicUsize, Ordering};
     use tempfile::TempDir;
 
+    #[test]
+    fn recipe_history_excludes_turn_context_events() {
+        use crate::conversation::message::MessageMetadata;
+
+        let history = Conversation::new_unvalidated([
+            Message::user().with_text("build me a recipe"),
+            Message::user()
+                .with_text("<turn-context>cwd /repo</turn-context>")
+                .with_metadata(MessageMetadata::agent_only().with_turn_context()),
+            Message::assistant().with_text("on it"),
+        ]);
+
+        let texts: Vec<String> = recipe_conversation_history(&history)
+            .iter()
+            .map(|message| message.as_concat_text())
+            .collect();
+        assert_eq!(texts, ["build me a recipe", "on it"]);
+    }
+
     async fn tracing_test_agent_and_session() -> (Agent, Session, TempDir) {
         let data_dir = TempDir::new().unwrap();
         let data_path = data_dir.path().to_path_buf();
diff --git a/crates/goose/src/agents/extension_manager.rs b/crates/goose/src/agents/extension_manager.rs
index 0d431a57ec..16a76c2c2e 100644
--- a/crates/goose/src/agents/extension_manager.rs
+++ b/crates/goose/src/agents/extension_manager.rs
@@ -2158,7 +2158,7 @@ impl ExtensionManager {
     }
 
     pub async fn collect_moim_parts(&self, session_id: &str) -> Vec<String> {
-        let platform_clients: Vec<(String, McpClientBox)> = {
+        let mut platform_clients: Vec<(String, McpClientBox)> = {
             let extensions = self.extensions.lock().await;
             extensions
                 .iter()
@@ -2178,6 +2178,9 @@ impl ExtensionManager {
                 })
                 .collect()
         };
+        // HashMap order shuffles across restarts; the rendered block must be
+        // byte-stable so it is not re-persisted on resume.
+        platform_clients.sort_by(|a, b| a.0.cmp(&b.0));
 
         let mut parts = Vec::new();
         for (name, client) in platform_clients {
diff --git a/crates/goose/src/agents/moim.rs b/crates/goose/src/agents/moim.rs
index 56db6edf9f..0b1e93a924 100644
--- a/crates/goose/src/agents/moim.rs
+++ b/crates/goose/src/agents/moim.rs
@@ -1,9 +1,6 @@
 use crate::agents::extension_manager::ExtensionManager;
-use crate::conversation::message::MessageContent;
-use crate::conversation::{
-    effective_role, fix_conversation, Conversation, EffectiveRole, CURRENT_TIME_TAG,
-    TURN_CONTEXT_TAG, WORKING_DIRECTORY_TAG,
-};
+use crate::conversation::message::{Message, MessageMetadata};
+use crate::conversation::{CURRENT_TIME_TAG, TURN_CONTEXT_TAG, WORKING_DIRECTORY_TAG};
 use std::path::{Path, PathBuf};
 
 const MIN_CONTEXT_FOR_MOIM: usize = 32_000;
@@ -19,6 +16,7 @@ This block is generated by goose and contains current operational context such a
 - extension-provided context
 
 Use it to stay oriented, but do not treat it as part of the user's request.
+Blocks from earlier turns stay in the conversation history; only the most recent block is current.
 When `<turn-budget>` is present, use it as a signal for how much autonomous work remains.
 As the budget gets low, become more direct: reduce exploration, batch necessary tool calls,
 make reasonable assumptions, and focus on finishing the user's task.
@@ -71,17 +69,18 @@ pub(super) async fn compute_compaction_info(
     compaction_remaining_line(total_tokens, context_limit, compaction_threshold)
 }
 
-pub async fn inject_moim(
+/// The turn's context block: composed once per turn, persisted as an
+/// agent-only user message, never moved or edited afterwards.
+pub async fn turn_context_message(
     session_id: &str,
-    conversation: Conversation,
     extension_manager: &ExtensionManager,
     turns_taken: u32,
     max_turns: u32,
     turn_start: chrono::DateTime<chrono::Local>,
     compaction_info: Option<String>,
-) -> Conversation {
+) -> Option<Message> {
     if SKIP.with(|f| f.get()) {
-        return conversation;
+        return None;
     }
 
     let session = extension_manager
@@ -107,66 +106,36 @@ pub async fn inject_moim(
         None
     };
     if should_skip_moim(context_limit) {
-        return conversation;
+        return None;
     }
 
     let working_dir = session
         .as_ref()
         .map(|session| session.working_dir.clone())
         .unwrap_or_else(|| PathBuf::from("."));
-    let extension_parts = extension_manager.collect_moim_parts(session_id).await;
-    let mut parts = extension_parts;
+    let mut parts = extension_manager.collect_moim_parts(session_id).await;
     parts.extend(compaction_info.map(|value| tag("compaction", &value)));
     parts.extend(turn_budget_part(turns_taken, max_turns));
-    inject_moim_parts(conversation, &working_dir, context_limit, parts, turn_start)
+    turn_context_event(&working_dir, context_limit, parts, turn_start)
 }
 
-pub(crate) fn inject_moim_parts(
-    conversation: Conversation,
+/// The state-machine variant: operations contribute the parts and the caller
+/// persists the event, so later requests in the turn reuse the same bytes.
+pub(crate) fn turn_context_event(
     working_dir: &Path,
     context_limit: Option<usize>,
     parts: Vec<String>,
     turn_start: chrono::DateTime<chrono::Local>,
-) -> Conversation {
+) -> Option<Message> {
     if SKIP.with(|f| f.get()) || should_skip_moim(context_limit) {
-        return conversation;
+        return None;
     }
 
-    let moim = compose_moim(working_dir, parts, turn_start);
-
-    let mut messages = conversation.messages().clone();
-    let Some(idx) = messages
-        .iter()
-        .rposition(|m| m.is_agent_visible() && effective_role(m) == EffectiveRole::User)
-    else {
-        return conversation;
-    };
-    let insert_idx = messages[idx]
-        .content
-        .iter()
-        .take_while(|content| matches!(content, MessageContent::ToolResponse(_)))
-        .count();
-    messages[idx]
-        .content
-        .insert(insert_idx, MessageContent::text(moim));
-
-    let (fixed, issues) = fix_conversation(Conversation::new_unvalidated(messages));
-
-    let has_unexpected_issues = issues.iter().any(|issue| {
-        !issue.contains("Merged consecutive user messages")
-            && !issue.contains("Merged consecutive assistant messages")
-            && !issue.contains("Added placeholder to empty tool result")
-            && !issue.contains("Trimmed trailing whitespace from assistant message")
-            && !issue.contains("Removed trailing assistant message")
-            && !issue.contains("Merged text content")
-    });
-
-    if has_unexpected_issues {
-        tracing::warn!("MOIM injection caused unexpected issues: {:?}", issues);
-        return conversation;
-    }
-
-    fixed
+    Some(
+        Message::user()
+            .with_text(compose_moim(working_dir, parts, turn_start))
+            .with_metadata(MessageMetadata::agent_only().with_turn_context()),
+    )
 }
 
 fn should_skip_moim(context_limit: Option<usize>) -> bool {
@@ -252,21 +221,8 @@ fn turn_budget_part(turns_taken: u32, max_turns: u32) -> Option<String> {
 #[cfg(test)]
 mod tests {
     use super::*;
-    use crate::conversation::message::Message;
-    use rmcp::model::CallToolRequestParams;
 
-    fn text_at(message: &crate::conversation::message::Message, index: usize) -> &str {
-        message.content[index].as_text().unwrap()
-    }
-
-    fn is_moim(content: &MessageContent) -> bool {
-        content
-            .as_text()
-            .is_some_and(|text| text.starts_with(&format!("<{}>\n", TURN_CONTEXT_TAG)))
-    }
-
-    #[tokio::test]
-    async fn test_moim_prepended_to_latest_user_message() {
+    async fn session_and_manager() -> (String, ExtensionManager, tempfile::TempDir) {
         let temp_dir = tempfile::tempdir().unwrap();
         let em = ExtensionManager::new_without_provider(temp_dir.path().to_path_buf());
         let session = em
@@ -280,209 +236,83 @@ mod tests {
             )
             .await
             .unwrap();
-
-        let conv = Conversation::new_unvalidated(vec![
-            Message::user().with_text("Hello"),
-            Message::assistant().with_text("Hi"),
-            Message::user().with_text("Bye"),
-        ]);
-        let result = inject_moim(&session.id, conv, &em, 0, 100, chrono::Local::now(), None).await;
-        let msgs = result.messages();
-
-        assert_eq!(msgs.len(), 3);
-        assert_eq!(text_at(&msgs[0], 0), "Hello");
-        assert_eq!(text_at(&msgs[1], 0), "Hi");
-        assert!(is_moim(&msgs[2].content[0]));
-        assert_eq!(text_at(&msgs[2], 1), "Bye");
+        (session.id, em, temp_dir)
     }
 
     #[tokio::test]
-    async fn test_moim_injection_no_assistant() {
-        let temp_dir = tempfile::tempdir().unwrap();
-        let em = ExtensionManager::new_without_provider(temp_dir.path().to_path_buf());
-        let session = em
-            .get_context()
-            .session_manager
-            .create_session(
-                PathBuf::from("/test/dir"),
-                "test".to_string(),
-                crate::session::SessionType::User,
-                crate::config::GooseMode::Auto,
-            )
+    async fn turn_context_message_is_an_agent_only_user_message() {
+        let (session_id, em, _tmp) = session_and_manager().await;
+
+        let message = turn_context_message(&session_id, &em, 0, 100, chrono::Local::now(), None)
             .await
-            .unwrap();
+            .expect("turn context should be produced");
 
-        let conv = Conversation::new_unvalidated(vec![Message::user().with_text("Hello")]);
-        let result = inject_moim(&session.id, conv, &em, 0, 100, chrono::Local::now(), None).await;
-
-        assert_eq!(result.messages().len(), 1);
-        assert!(is_moim(&result.messages()[0].content[0]));
-        assert_eq!(text_at(&result.messages()[0], 1), "Hello");
+        assert_eq!(message.role, rmcp::model::Role::User);
+        assert!(message.is_agent_visible());
+        assert!(!message.is_user_visible());
+        assert!(message.is_turn_context());
+        let text = message.content[0].as_text().unwrap();
+        assert!(text.starts_with(&format!("<{TURN_CONTEXT_TAG}>\n")));
+        assert!(text.trim_end().ends_with(&format!("</{TURN_CONTEXT_TAG}>")));
     }
 
     #[tokio::test]
-    async fn test_moim_skips_user_messages_not_visible_to_agent() {
-        let temp_dir = tempfile::tempdir().unwrap();
-        let em = ExtensionManager::new_without_provider(temp_dir.path().to_path_buf());
-        let session = em
-            .get_context()
-            .session_manager
-            .create_session(
-                PathBuf::from("/test/dir"),
-                "test".to_string(),
-                crate::session::SessionType::User,
-                crate::config::GooseMode::Auto,
-            )
+    async fn turn_context_bytes_are_stable_for_a_turn() {
+        let (session_id, em, _tmp) = session_and_manager().await;
+        let turn_start = chrono::Local::now();
+
+        let first = turn_context_message(&session_id, &em, 0, 100, turn_start, None)
+            .await
+            .unwrap();
+        let second = turn_context_message(&session_id, &em, 0, 100, turn_start, None)
             .await
             .unwrap();
 
-        let conv = Conversation::new_unvalidated(vec![
-            Message::user().with_text("agent visible"),
-            Message::assistant().with_text("reply"),
-            Message::user().with_text("user only").user_only(),
-        ]);
-        let result = inject_moim(&session.id, conv, &em, 0, 100, chrono::Local::now(), None).await;
-        let msgs = result.messages();
-
-        assert_eq!(msgs.len(), 2);
-        assert!(is_moim(&msgs[0].content[0]));
-        assert_eq!(text_at(&msgs[0], 1), "agent visible");
-        assert_eq!(text_at(&msgs[1], 0), "user only");
-        assert!(!msgs[1].is_agent_visible());
+        assert_eq!(
+            first.content[0].as_text(),
+            second.content[0].as_text(),
+            "the same turn inputs must render byte-identical blocks"
+        );
     }
 
-    #[tokio::test]
-    async fn test_moim_with_tool_calls() {
-        let temp_dir = tempfile::tempdir().unwrap();
-        let em = ExtensionManager::new_without_provider(temp_dir.path().to_path_buf());
-        let session = em
-            .get_context()
-            .session_manager
-            .create_session(
-                PathBuf::from("/test/dir"),
-                "test".to_string(),
-                crate::session::SessionType::User,
-                crate::config::GooseMode::Auto,
-            )
-            .await
-            .unwrap();
+    #[test]
+    fn turn_context_event_is_marked_and_skips_small_contexts() {
+        let event = turn_context_event(
+            Path::new("/test/dir"),
+            Some(200_000),
+            vec![],
+            chrono::Local::now(),
+        )
+        .expect("large-context models should get a turn-context event");
+        assert!(event.is_turn_context());
+        assert!(!event.is_user_visible());
 
-        let conv = Conversation::new_unvalidated(vec![
-            Message::user().with_text("Search for something"),
-            Message::assistant()
-                .with_text("I'll search for you")
-                .with_tool_request("search_1", Ok(CallToolRequestParams::new("search"))),
-            Message::user()
-                .with_tool_response("search_1", Ok(rmcp::model::CallToolResult::success(vec![]))),
-        ]);
-
-        let result = inject_moim(&session.id, conv, &em, 0, 100, chrono::Local::now(), None).await;
-        let msgs = result.messages();
-
-        assert_eq!(msgs.len(), 3);
-        assert!(is_moim(&msgs[0].content[0]));
-        assert_eq!(text_at(&msgs[0], 1), "Search for something");
-        assert!(matches!(
-            &msgs[2].content[0],
-            MessageContent::ToolResponse(_)
-        ));
-        assert_eq!(msgs[2].content.len(), 1);
+        assert!(turn_context_event(
+            Path::new("/test/dir"),
+            Some(16_000),
+            vec![],
+            chrono::Local::now(),
+        )
+        .is_none());
     }
 
-    /// The turn-context block is produced here (`compose_moim`, in goose) but
-    /// recognized in a different crate (`is_turn_context_text`, in
-    /// goose-providers) by matching its textual shape. That recognition is the
-    /// only thing that keeps the volatile block out of the Anthropic cache
-    /// prefix. The two are coupled by string layout alone, with no shared type
-    /// or compiler check, so a reorder or rename on either side would silently
-    /// collapse prompt caching. These tests fail loudly if they drift apart.
-    mod turn_context_detector_coupling {
-        use super::*;
-        use crate::conversation::is_turn_context_text;
-        use std::path::Path;
+    #[test]
+    fn current_time_is_timezone_aware() {
+        let block = compose_moim(
+            Path::new("/Users/me/code/goose"),
+            vec![],
+            chrono::Local::now(),
+        );
+        let time_line = block
+            .lines()
+            .find(|line| line.starts_with(&format!("<{CURRENT_TIME_TAG}>")))
+            .expect("turn-context block should contain a current-time line");
 
-        fn moim(
-            total_tokens: Option<i32>,
-            context_limit: Option<usize>,
-            turns_taken: u32,
-            max_turns: u32,
-            mut parts: Vec<String>,
-        ) -> String {
-            parts.extend(
-                compaction_remaining_line(total_tokens, context_limit, 0.8)
-                    .map(|value| tag("compaction", &value)),
-            );
-            parts.extend(turn_budget_part(turns_taken, max_turns));
-            compose_moim(
-                Path::new("/Users/me/code/goose"),
-                parts,
-                chrono::Local::now(),
-            )
-        }
+        let value = time_line
+            .trim_start_matches(&format!("<{CURRENT_TIME_TAG}>"))
+            .trim_end_matches(&format!("</{CURRENT_TIME_TAG}>"));
 
-        #[test]
-        fn compose_moim_output_is_recognized_by_the_anthropic_detector() {
-            let guardrail = || vec!["<guardrail>stay on task</guardrail>".to_string()];
-            let cases = [
-                ("minimal", moim(None, None, 0, 0, vec![])),
-                (
-                    "with compaction line",
-                    moim(Some(100_000), Some(200_000), 0, 0, vec![]),
-                ),
-                ("with turn-budget line", moim(None, None, 20, 40, vec![])),
-                (
-                    "with extension context",
-                    moim(None, None, 0, 0, guardrail()),
-                ),
-                (
-                    "fully populated",
-                    moim(Some(100_000), Some(200_000), 20, 40, guardrail()),
-                ),
-            ];
-
-            for (label, block) in &cases {
-                assert!(
-                    is_turn_context_text(block),
-                    "is_turn_context_text rejected real compose_moim output ({label}); the \
-                     producer in goose and the detector in goose-providers have drifted, so the \
-                     volatile block will no longer be kept out of the Anthropic cache prefix:\n\
-                     {block}"
-                );
-            }
-        }
-
-        #[test]
-        fn detector_rejects_text_that_is_not_a_turn_context_block() {
-            assert!(
-                !is_turn_context_text("Please refactor the argument parser."),
-                "ordinary user text must not be treated as a turn-context block"
-            );
-            assert!(
-                !is_turn_context_text(
-                    "<turn-context>\n\
-                     <current-time>2026-06-25 12:00:00</current-time>\n\
-                     <session-id>abc</session-id>\n\
-                     </turn-context>"
-                ),
-                "a block whose first field after current-time is not working-directory must not \
-                 match: the detector's shape checks are what discriminate the injected block"
-            );
-        }
-
-        #[test]
-        fn current_time_is_timezone_aware() {
-            let block = moim(None, None, 0, 0, vec![]);
-            let time_line = block
-                .lines()
-                .find(|line| line.starts_with(&format!("<{CURRENT_TIME_TAG}>")))
-                .expect("turn-context block should contain a current-time line");
-
-            let value = time_line
-                .trim_start_matches(&format!("<{CURRENT_TIME_TAG}>"))
-                .trim_end_matches(&format!("</{CURRENT_TIME_TAG}>"));
-
-            chrono::DateTime::parse_from_str(value, "%Y-%m-%d %H:%M:%S %:z")
-                .expect("current-time should include a numeric UTC offset");
-        }
+        chrono::DateTime::parse_from_str(value, "%Y-%m-%d %H:%M:%S %:z")
+            .expect("current-time should include a numeric UTC offset");
     }
 }
diff --git a/crates/goose/src/agents/platform_extensions/chatrecall.rs b/crates/goose/src/agents/platform_extensions/chatrecall.rs
index 7f76f0868e..0e437bfdbf 100644
--- a/crates/goose/src/agents/platform_extensions/chatrecall.rs
+++ b/crates/goose/src/agents/platform_extensions/chatrecall.rs
@@ -41,7 +41,11 @@ pub struct ChatRecallClient {
 }
 
 fn format_agent_visible_excerpt(conversation: &Conversation) -> Option<(usize, String)> {
-    let messages = conversation.agent_visible_messages();
+    let messages: Vec<_> = conversation
+        .agent_visible_messages()
+        .into_iter()
+        .filter(|message| !message.is_turn_context())
+        .collect();
     let total = messages.len();
     if total == 0 {
         return None;
diff --git a/crates/goose/src/agents/platform_extensions/orchestrator.rs b/crates/goose/src/agents/platform_extensions/orchestrator.rs
index 1da47dda79..b8e0852d00 100644
--- a/crates/goose/src/agents/platform_extensions/orchestrator.rs
+++ b/crates/goose/src/agents/platform_extensions/orchestrator.rs
@@ -336,12 +336,13 @@ impl OrchestratorClient {
     ) -> Result<String, String> {
         let provider = self.get_provider().await?;
 
-        let conversation_text = Conversation::new_unvalidated(messages.iter().cloned())
-            .agent_visible_messages()
-            .iter()
-            .map(format_message_for_compacting)
-            .collect::<Vec<_>>()
-            .join("\n");
+        let conversation_text = agent_visible_session_messages(&Conversation::new_unvalidated(
+            messages.iter().cloned(),
+        ))
+        .iter()
+        .map(format_message_for_compacting)
+        .collect::<Vec<_>>()
+        .join("\n");
 
         let system =
             "You are a helpful assistant. Summarize the following conversation concisely, \
@@ -578,7 +579,11 @@ impl OrchestratorClient {
 }
 
 fn agent_visible_session_messages(conversation: &Conversation) -> Vec<Message> {
-    conversation.agent_visible_messages()
+    conversation
+        .agent_visible_messages()
+        .into_iter()
+        .filter(|message| !message.is_turn_context())
+        .collect()
 }
 
 #[async_trait]
diff --git a/crates/goose/src/agents/reply_parts.rs b/crates/goose/src/agents/reply_parts.rs
index ebb4f55aa4..52670dd2eb 100644
--- a/crates/goose/src/agents/reply_parts.rs
+++ b/crates/goose/src/agents/reply_parts.rs
@@ -14,7 +14,7 @@ use super::gen_ai_telemetry;
 use crate::agents::platform_extensions::code_execution;
 use crate::config::{Config, GooseMode};
 use crate::conversation::message::{Message, MessageContent, MessageUsage, ToolRequest};
-use crate::conversation::{fix_conversation, Conversation};
+use crate::conversation::{fix_conversation, merge_consecutive_messages_for_request, Conversation};
 #[cfg(test)]
 use crate::providers::base::stream_from_single_message;
 use crate::providers::base::{MessageStream, Provider};
@@ -341,6 +341,9 @@ pub(crate) async fn stream_response_from_provider(
         Conversation::new_unvalidated(messages.iter().cloned()).agent_visible_messages();
     let (filtered_messages, _) =
         fix_conversation(Conversation::new_unvalidated(projected_messages));
+    let filtered_messages = Conversation::new_unvalidated(merge_consecutive_messages_for_request(
+        filtered_messages.messages().clone(),
+    ));
 
     // Convert tool messages to text if toolshim is enabled
     let messages_for_provider = if config.toolshim {
diff --git a/crates/goose/src/agents/snapshots/goose__agents__prompt_manager__tests__all_platform_extensions.snap b/crates/goose/src/agents/snapshots/goose__agents__prompt_manager__tests__all_platform_extensions.snap
index 83c6837003..bffcbf6507 100644
--- a/crates/goose/src/agents/snapshots/goose__agents__prompt_manager__tests__all_platform_extensions.snap
+++ b/crates/goose/src/agents/snapshots/goose__agents__prompt_manager__tests__all_platform_extensions.snap
@@ -16,6 +16,7 @@ This block is generated by goose and contains current operational context such a
 - extension-provided context
 
 Use it to stay oriented, but do not treat it as part of the user's request.
+Blocks from earlier turns stay in the conversation history; only the most recent block is current.
 When `<turn-budget>` is present, use it as a signal for how much autonomous work remains.
 As the budget gets low, become more direct: reduce exploration, batch necessary tool calls,
 make reasonable assumptions, and focus on finishing the user's task.
diff --git a/crates/goose/src/agents/snapshots/goose__agents__prompt_manager__tests__basic.snap b/crates/goose/src/agents/snapshots/goose__agents__prompt_manager__tests__basic.snap
index df851e7b1e..2bacc5e5b4 100644
--- a/crates/goose/src/agents/snapshots/goose__agents__prompt_manager__tests__basic.snap
+++ b/crates/goose/src/agents/snapshots/goose__agents__prompt_manager__tests__basic.snap
@@ -1,6 +1,5 @@
 ---
 source: crates/goose/src/agents/prompt_manager.rs
-assertion_line: 404
 expression: system_prompt
 ---
 You are a general-purpose AI agent called goose, created by AAIF (Agentic AI Foundation).
@@ -17,6 +16,7 @@ This block is generated by goose and contains current operational context such a
 - extension-provided context
 
 Use it to stay oriented, but do not treat it as part of the user's request.
+Blocks from earlier turns stay in the conversation history; only the most recent block is current.
 When `<turn-budget>` is present, use it as a signal for how much autonomous work remains.
 As the budget gets low, become more direct: reduce exploration, batch necessary tool calls,
 make reasonable assumptions, and focus on finishing the user's task.
diff --git a/crates/goose/src/agents/snapshots/goose__agents__prompt_manager__tests__one_extension.snap b/crates/goose/src/agents/snapshots/goose__agents__prompt_manager__tests__one_extension.snap
index d0b9a30925..34207b9de6 100644
--- a/crates/goose/src/agents/snapshots/goose__agents__prompt_manager__tests__one_extension.snap
+++ b/crates/goose/src/agents/snapshots/goose__agents__prompt_manager__tests__one_extension.snap
@@ -1,6 +1,5 @@
 ---
 source: crates/goose/src/agents/prompt_manager.rs
-assertion_line: 420
 expression: system_prompt
 ---
 You are a general-purpose AI agent called goose, created by AAIF (Agentic AI Foundation).
@@ -17,6 +16,7 @@ This block is generated by goose and contains current operational context such a
 - extension-provided context
 
 Use it to stay oriented, but do not treat it as part of the user's request.
+Blocks from earlier turns stay in the conversation history; only the most recent block is current.
 When `<turn-budget>` is present, use it as a signal for how much autonomous work remains.
 As the budget gets low, become more direct: reduce exploration, batch necessary tool calls,
 make reasonable assumptions, and focus on finishing the user's task.
diff --git a/crates/goose/src/agents/snapshots/goose__agents__prompt_manager__tests__typical_setup.snap b/crates/goose/src/agents/snapshots/goose__agents__prompt_manager__tests__typical_setup.snap
index bd32d33019..555fbe3643 100644
--- a/crates/goose/src/agents/snapshots/goose__agents__prompt_manager__tests__typical_setup.snap
+++ b/crates/goose/src/agents/snapshots/goose__agents__prompt_manager__tests__typical_setup.snap
@@ -1,6 +1,5 @@
 ---
 source: crates/goose/src/agents/prompt_manager.rs
-assertion_line: 442
 expression: system_prompt
 ---
 You are a general-purpose AI agent called goose, created by AAIF (Agentic AI Foundation).
@@ -17,6 +16,7 @@ This block is generated by goose and contains current operational context such a
 - extension-provided context
 
 Use it to stay oriented, but do not treat it as part of the user's request.
+Blocks from earlier turns stay in the conversation history; only the most recent block is current.
 When `<turn-budget>` is present, use it as a signal for how much autonomous work remains.
 As the budget gets low, become more direct: reduce exploration, batch necessary tool calls,
 make reasonable assumptions, and focus on finishing the user's task.
diff --git a/crates/goose/src/agents/state_machine/ops_llm.rs b/crates/goose/src/agents/state_machine/ops_llm.rs
index c693838b70..b1e2d29049 100644
--- a/crates/goose/src/agents/state_machine/ops_llm.rs
+++ b/crates/goose/src/agents/state_machine/ops_llm.rs
@@ -434,18 +434,32 @@ impl Inference for InferenceRunner<'_> {
                 .get_context_limit(&self.model_config)
                 .await
                 .unwrap_or_else(|_| self.model_config.context_limit());
-            let turn_start = messages_since_kickoff(conversation)?
+            let turn = messages_since_kickoff(conversation)?;
+            let turn_start = turn
                 .first()
                 .and_then(|message| chrono::DateTime::from_timestamp(message.created, 0))
                 .map(|timestamp| timestamp.with_timezone(&chrono::Local))
                 .unwrap_or_else(chrono::Local::now);
-            let conversation_for_provider = crate::agents::moim::inject_moim_parts(
-                Conversation::new_unvalidated(messages_for_provider),
+            // Persist a fresh turn-context event only when its bytes changed
+            // (e.g. the turn budget ticked); earlier events stay in place.
+            let last_turn_context = turn
+                .iter()
+                .rev()
+                .find(|message| message.is_turn_context())
+                .map(Message::as_concat_text);
+            let turn_context = crate::agents::moim::turn_context_event(
                 &session.working_dir,
                 Some(context_limit),
                 input.moim_parts,
                 turn_start,
-            );
+            )
+            .filter(|event| Some(event.as_concat_text()) != last_turn_context);
+            if let Some(event) = &turn_context {
+                messages_for_provider.push(event.clone());
+            }
+            let conversation_for_provider = Conversation::new_unvalidated(messages_for_provider);
+            let mut usage_effects: Vec<StateEffect> =
+                turn_context.into_iter().map(StateEffect::from).collect();
 
             let stream = crate::agents::reply_parts::stream_response_from_provider(
                 self.provider.clone(),
@@ -460,7 +474,10 @@ impl Inference for InferenceRunner<'_> {
 
             let mut stream = match stream {
                 Ok(stream) => stream,
-                Err(err) => return applied(self.error_outcome(&err, emit).await),
+                Err(err) => {
+                    usage_effects.extend(self.error_outcome(&err, emit).await);
+                    return applied(usage_effects);
+                }
             };
 
             let requested_model = self.model_config.model_name.clone();
@@ -477,7 +494,6 @@ impl Inference for InferenceRunner<'_> {
                 });
 
             let mut accumulator = Conversation::empty();
-            let mut usage_effects = Vec::new();
             let mut tool_request_ids = std::collections::HashSet::new();
             loop {
                 tokio::select! {
@@ -540,7 +556,10 @@ impl Inference for InferenceRunner<'_> {
                 return yielded_with(usage_effects);
             }
 
-            if usage_effects.is_empty() {
+            let has_recorded_usage = usage_effects
+                .iter()
+                .any(|effect| matches!(effect, StateEffect::RecordUsage(_)));
+            if !has_recorded_usage {
                 let mut usage = ProviderUsage::new(
                     self.model_config.model_name.clone(),
                     goose_providers::conversation::token_usage::Usage::default(),
diff --git a/crates/goose/src/agents/state_machine/ops_toolcalling.rs b/crates/goose/src/agents/state_machine/ops_toolcalling.rs
index 175c94d071..519faf1861 100644
--- a/crates/goose/src/agents/state_machine/ops_toolcalling.rs
+++ b/crates/goose/src/agents/state_machine/ops_toolcalling.rs
@@ -648,6 +648,8 @@ impl Operation for ToolExecutionOperation<'_> {
         if extensions.is_empty() {
             return Ok(prompt_parts);
         }
+        // HashMap order shuffles across restarts and would bust the prompt cache.
+        extensions.sort_by(|a, b| a.name.cmp(&b.name));
 
         let mut lines = vec![
             "# Extensions".to_string(),
diff --git a/crates/goose/src/agents/state_machine/tests/mod.rs b/crates/goose/src/agents/state_machine/tests/mod.rs
index 753a939f98..f5f2ad7ee6 100644
--- a/crates/goose/src/agents/state_machine/tests/mod.rs
+++ b/crates/goose/src/agents/state_machine/tests/mod.rs
@@ -49,6 +49,35 @@ async fn max_turns_counts_inference_calls_and_injects_budget() -> Result<()> {
     Ok(())
 }
 
+#[tokio::test]
+async fn turn_context_is_persisted_once_per_turn_and_reused_across_inferences() -> Result<()> {
+    let (pipeline, api) = test_pipeline().await?;
+    api.on("add one").call(ADD, value(1));
+    api.on("result: 1").reply("The total is 1");
+    api.on("hello").reply("hi there!");
+
+    let result = pipeline.run(["add one", "hello"]).await?;
+
+    let conversation = result.conversation();
+    let events: Vec<_> = conversation
+        .messages()
+        .iter()
+        .filter(|message| message.is_turn_context())
+        .collect();
+    assert_eq!(
+        events.len(),
+        2,
+        "one turn-context event per turn; the turn's second inference reuses it"
+    );
+    assert!(events.iter().all(|event| !event.is_user_visible()));
+    assert!(api
+        .calls()
+        .iter()
+        .all(|call| call.input_contains("<turn-context>")));
+
+    Ok(())
+}
+
 #[tokio::test]
 async fn goal_starts_nudges_and_clears_when_met() -> Result<()> {
     let (pipeline, api) = test_pipeline().await?;
diff --git a/crates/goose/src/agents/state_machine/tests/pipeline.rs b/crates/goose/src/agents/state_machine/tests/pipeline.rs
index f661ca788e..34d8bb3f90 100644
--- a/crates/goose/src/agents/state_machine/tests/pipeline.rs
+++ b/crates/goose/src/agents/state_machine/tests/pipeline.rs
@@ -970,6 +970,7 @@ impl TestRun {
             .conversation()
             .messages()
             .iter()
+            .filter(|message| !message.is_turn_context())
             .flat_map(|message| {
                 message
                     .content
diff --git a/crates/goose/src/agents/state_machine/tests/recipe_scheduling_lifecycle.rs b/crates/goose/src/agents/state_machine/tests/recipe_scheduling_lifecycle.rs
index ed10eef866..50747d8fd3 100644
--- a/crates/goose/src/agents/state_machine/tests/recipe_scheduling_lifecycle.rs
+++ b/crates/goose/src/agents/state_machine/tests/recipe_scheduling_lifecycle.rs
@@ -266,7 +266,12 @@ async fn scheduler_is_advertised_only_when_configured_and_manages_jobs() -> Resu
     assert_eq!(scheduled_sessions.len(), 1);
     assert_eq!(
         scheduled_sessions[0].1.message_count,
-        listed.conversation().messages().len()
+        listed
+            .conversation()
+            .messages()
+            .iter()
+            .filter(|message| message.is_user_visible())
+            .count()
     );
     api.on("list scheduled runs").call(
         MANAGE_SCHEDULE_TOOL_NAME_COMPLETE,
diff --git a/crates/goose/src/context_mgmt/mod.rs b/crates/goose/src/context_mgmt/mod.rs
index aa66359939..a451dcec27 100644
--- a/crates/goose/src/context_mgmt/mod.rs
+++ b/crates/goose/src/context_mgmt/mod.rs
@@ -100,9 +100,13 @@ pub async fn compact_messages(
         has_text && !has_tool_content
     };
 
-    let (preserved_user_message, is_most_recent) = if !manual_compact {
+    // Turn-context events are agent-appended, never the message to preserve.
+    let (preserved_user_message, preserved_idx, is_most_recent) = if !manual_compact {
         let found_msg = messages.iter().enumerate().rev().find_map(|(idx, msg)| {
-            if !msg.is_agent_visible() || !matches!(msg.role, rmcp::model::Role::User) {
+            if !msg.is_agent_visible()
+                || msg.is_turn_context()
+                || !matches!(msg.role, rmcp::model::Role::User)
+            {
                 return None;
             }
 
@@ -123,13 +127,13 @@ pub async fn compact_messages(
         });
 
         if let Some((idx, msg)) = found_msg {
-            let is_last = idx == messages.len() - 1;
-            (Some(msg), is_last)
+            let is_last = messages[idx + 1..].iter().all(Message::is_turn_context);
+            (Some(msg), Some(idx), is_last)
         } else {
-            (None, false)
+            (None, None, false)
         }
     } else {
-        (None, false)
+        (None, None, false)
     };
 
     let messages_to_compact = messages.as_slice();
@@ -175,6 +179,25 @@ pub async fn compact_messages(
         final_messages.push(user_msg);
     }
 
+    // Carry the turn's own context event (it follows the preserved prompt) so
+    // a mid-turn retry keeps it; anything earlier belongs to a previous turn.
+    if let Some(carry_from) = preserved_idx.map(|idx| idx + 1) {
+        if let Some(turn_context) = messages_to_compact[carry_from..]
+            .iter()
+            .rev()
+            .find(|msg| msg.is_turn_context() && msg.is_agent_visible())
+        {
+            let mut carried = turn_context.clone();
+            carried.id = None;
+            // Storage reloads order by created_timestamp; the copy must keep
+            // its appended position, not resurface at the original event's time.
+            if let Some(latest) = final_messages.iter().map(|msg| msg.created).max() {
+                carried.created = carried.created.max(latest);
+            }
+            final_messages.push(carried);
+        }
+    }
+
     let conversation = Conversation::new_unvalidated(final_messages);
     let retained_context_tokens = match count_context_tokens(&conversation).await {
         Ok(tokens) => tokens,
@@ -317,8 +340,14 @@ async fn do_compact(
     session_id: &str,
     messages: &[Message],
 ) -> Result<(Message, ProviderUsage), anyhow::Error> {
-    let agent_visible_messages =
-        Conversation::new_unvalidated(messages.iter().cloned()).agent_visible_messages();
+    // Keep stale per-turn state out of the summary.
+    let agent_visible_messages = Conversation::new_unvalidated(
+        messages
+            .iter()
+            .filter(|msg| !msg.is_turn_context())
+            .cloned(),
+    )
+    .agent_visible_messages();
 
     // Try progressively removing more tool response messages from the middle to reduce context length
     let removal_percentages = [0, 10, 20, 50, 100];
@@ -697,6 +726,7 @@ mod tests {
         message: Message,
         config: ModelConfig,
         max_tool_responses: Option<usize>,
+        captured_system: std::sync::Mutex<Option<String>>,
     }
 
     impl MockProvider {
@@ -715,6 +745,7 @@ mod tests {
                     request_headers: None,
                 },
                 max_tool_responses: None,
+                captured_system: std::sync::Mutex::new(None),
             }
         }
 
@@ -733,10 +764,11 @@ mod tests {
         async fn stream(
             &self,
             _model_config: &ModelConfig,
-            _system: &str,
+            system: &str,
             messages: &[Message],
             _tools: &[Tool],
         ) -> Result<MessageStream, ProviderError> {
+            *self.captured_system.lock().unwrap() = Some(system.to_string());
             // If max_tool_responses is set, fail if we have too many
             if let Some(max) = self.max_tool_responses {
                 let tool_response_count = messages
@@ -956,6 +988,198 @@ mod tests {
         assert!(!user_text.contains("assistant-only preprompt"));
     }
 
+    #[tokio::test]
+    async fn preserved_user_message_skips_turn_context_events() {
+        let conversation = Conversation::new_unvalidated([
+            Message::user().with_text("earlier request"),
+            Message::assistant().with_text("earlier response"),
+            Message::user().with_text("the real current request"),
+            Message::user()
+                .with_text("<turn-context>frozen block</turn-context>")
+                .with_metadata(MessageMetadata::agent_only().with_turn_context()),
+        ]);
+        let provider = MockProvider::new(Message::assistant().with_text("summary"), 1000);
+
+        let compacted = compact_messages(
+            &provider,
+            &provider.config,
+            "test-session-id",
+            &conversation,
+            false,
+        )
+        .await
+        .unwrap()
+        .conversation;
+
+        let preserved: Vec<_> = compacted
+            .messages()
+            .iter()
+            .filter(|message| message.is_agent_visible() && message.role == Role::User)
+            .collect();
+        let turn_context_events: Vec<_> = preserved
+            .iter()
+            .filter(|message| message.is_turn_context())
+            .collect();
+        let [carried_block] = turn_context_events.as_slice() else {
+            panic!("expected exactly one carried turn-context event");
+        };
+        assert!(
+            carried_block.as_concat_text().contains("frozen block"),
+            "the turn's context event must be carried forward for the mid-turn retry"
+        );
+        let last = compacted.messages().last().unwrap();
+        assert!(
+            last.is_turn_context() && last.is_agent_visible(),
+            "the carried event must trail the preserved user message"
+        );
+        let user_prompt = preserved[preserved.len() - 2];
+        assert!(
+            user_prompt
+                .as_concat_text()
+                .contains("the real current request"),
+            "the user's prompt must survive compaction verbatim"
+        );
+        assert!(!user_prompt.is_turn_context());
+
+        let continuation = compacted
+            .messages()
+            .iter()
+            .find(|message| message.role == Role::Assistant && message.is_agent_visible())
+            .unwrap()
+            .as_concat_text();
+        assert!(
+            continuation.contains(CONVERSATION_CONTINUATION_TEXT),
+            "a trailing turn-context event must not demote the compaction to a tool-loop continuation"
+        );
+    }
+
+    #[tokio::test]
+    async fn stale_turn_context_from_an_earlier_turn_is_not_carried() {
+        let conversation = Conversation::new_unvalidated([
+            Message::user().with_text("earlier request"),
+            Message::user()
+                .with_text("<turn-context>stale block</turn-context>")
+                .with_metadata(MessageMetadata::agent_only().with_turn_context()),
+            Message::assistant().with_text("earlier response"),
+            Message::user().with_text("the new prompt"),
+        ]);
+        let provider = MockProvider::new(Message::assistant().with_text("summary"), 1000);
+
+        let compacted = compact_messages(
+            &provider,
+            &provider.config,
+            "test-session-id",
+            &conversation,
+            false,
+        )
+        .await
+        .unwrap()
+        .conversation;
+
+        assert!(
+            !compacted
+                .messages()
+                .iter()
+                .any(|message| message.is_agent_visible() && message.is_turn_context()),
+            "pre-turn compaction must not resurrect a previous turn's context event"
+        );
+        let last = compacted.messages().last().unwrap();
+        assert_eq!(last.as_concat_text(), "the new prompt");
+    }
+
+    #[tokio::test]
+    async fn carried_turn_context_stays_last_after_persist_and_reload() {
+        let provider = MockProvider::new(Message::assistant().with_text("summary"), 1000);
+        let mut prompt = Message::user().with_text("the real current request");
+        prompt.created -= 3600;
+        let mut block = Message::user()
+            .with_text("<turn-context>frozen block</turn-context>")
+            .with_metadata(MessageMetadata::agent_only().with_turn_context());
+        block.created -= 3600;
+        let conversation = Conversation::new_unvalidated([prompt, block]);
+
+        let compacted = compact_messages(
+            &provider,
+            &provider.config,
+            "test-session-id",
+            &conversation,
+            false,
+        )
+        .await
+        .unwrap()
+        .conversation;
+        assert!(compacted.messages().last().unwrap().is_turn_context());
+
+        let temp_dir = tempfile::tempdir().unwrap();
+        let manager = crate::session::SessionManager::new(temp_dir.path().to_path_buf());
+        let session = manager
+            .create_session(
+                std::path::PathBuf::from("/tmp/test"),
+                "carry order".to_string(),
+                crate::session::session_manager::SessionType::User,
+                crate::config::GooseMode::default(),
+            )
+            .await
+            .unwrap();
+        manager
+            .replace_conversation(&session.id, &compacted)
+            .await
+            .unwrap();
+
+        let reloaded = manager
+            .get_session(&session.id, true)
+            .await
+            .unwrap()
+            .conversation
+            .unwrap();
+        assert_eq!(reloaded.messages().len(), compacted.messages().len());
+        let last = reloaded.messages().last().unwrap();
+        assert!(
+            last.is_turn_context(),
+            "the carried event must not resurface at its original timestamp on reload"
+        );
+    }
+
+    #[tokio::test]
+    async fn summarizer_input_excludes_turn_context_events() {
+        let provider = MockProvider::new(Message::assistant().with_text("summary"), 1000);
+        let turn_context = |text: &str| {
+            Message::user()
+                .with_text(text)
+                .with_metadata(MessageMetadata::agent_only().with_turn_context())
+        };
+        let conversation = Conversation::new_unvalidated([
+            Message::user().with_text("please refactor the parser"),
+            turn_context("<turn-context>cwd /old/dir</turn-context>"),
+            Message::assistant().with_text("working on it"),
+            turn_context("<turn-context>cwd /new/dir</turn-context>"),
+        ]);
+
+        let compacted = compact_messages(
+            &provider,
+            &provider.config,
+            "test-session-id",
+            &conversation,
+            false,
+        )
+        .await
+        .unwrap()
+        .conversation;
+
+        let system = provider.captured_system.lock().unwrap().clone().unwrap();
+        assert!(system.contains("please refactor the parser"));
+        assert!(
+            !system.contains("/old/dir") && !system.contains("/new/dir"),
+            "turn-context events must not reach the summarizer as dialogue"
+        );
+
+        let carried = compacted.messages().last().unwrap();
+        assert!(
+            carried.is_turn_context() && carried.as_concat_text().contains("/new/dir"),
+            "the newest turn-context event must still be carried forward"
+        );
+    }
+
     #[tokio::test]
     async fn tool_pair_summary_projects_nested_audiences_before_provider_input() {
         let provider = MockProvider::new(Message::assistant().with_text("summary"), 1000);
diff --git a/crates/goose/src/providers/litellm.rs b/crates/goose/src/providers/litellm.rs
index e9caf70f57..73ed45005b 100644
--- a/crates/goose/src/providers/litellm.rs
+++ b/crates/goose/src/providers/litellm.rs
@@ -1,10 +1,11 @@
 use anyhow::Result;
 use async_trait::async_trait;
 use futures::future::BoxFuture;
+use goose_providers::cache_semantics::apply_chat_payload_breakpoints;
 use goose_providers::conversation::token_usage::ProviderUsage;
 use goose_providers::errors::ProviderError;
 use goose_providers::images::ImageFormat;
-use serde_json::{json, Value};
+use serde_json::Value;
 use std::collections::HashMap;
 
 use super::api_client::{ApiClient, AuthMethod};
@@ -248,7 +249,7 @@ impl Provider for LiteLLMProvider {
         )?;
 
         if self.supports_cache_control(model_config).await {
-            payload = update_request_for_cache_control(&payload);
+            apply_chat_payload_breakpoints(&mut payload);
         }
 
         let response = self
@@ -280,71 +281,6 @@ impl Provider for LiteLLMProvider {
     }
 }
 
-/// Updates the request payload to include cache control headers for automatic prompt caching
-/// Adds ephemeral cache control to the last 2 user messages, system message, and last tool
-pub fn update_request_for_cache_control(original_payload: &Value) -> Value {
-    let mut payload = original_payload.clone();
-
-    if let Some(messages_spec) = payload
-        .as_object_mut()
-        .and_then(|obj| obj.get_mut("messages"))
-        .and_then(|messages| messages.as_array_mut())
-    {
-        let mut user_count = 0;
-        for message in messages_spec.iter_mut().rev() {
-            if message.get("role") == Some(&json!("user")) {
-                if let Some(content) = message.get_mut("content") {
-                    if let Some(content_str) = content.as_str() {
-                        *content = json!([{
-                            "type": "text",
-                            "text": content_str,
-                            "cache_control": { "type": "ephemeral" }
-                        }]);
-                    }
-                }
-                user_count += 1;
-                if user_count >= 2 {
-                    break;
-                }
-            }
-        }
-
-        if let Some(system_message) = messages_spec
-            .iter_mut()
-            .find(|msg| msg.get("role") == Some(&json!("system")))
-        {
-            if let Some(content) = system_message.get_mut("content") {
-                if let Some(content_str) = content.as_str() {
-                    *system_message = json!({
-                        "role": "system",
-                        "content": [{
-                            "type": "text",
-                            "text": content_str,
-                            "cache_control": { "type": "ephemeral" }
-                        }]
-                    });
-                }
-            }
-        }
-    }
-
-    if let Some(tools_spec) = payload
-        .as_object_mut()
-        .and_then(|obj| obj.get_mut("tools"))
-        .and_then(|tools| tools.as_array_mut())
-    {
-        if let Some(last_tool) = tools_spec.last_mut() {
-            if let Some(function) = last_tool.get_mut("function") {
-                function
-                    .as_object_mut()
-                    .unwrap()
-                    .insert("cache_control".to_string(), json!({ "type": "ephemeral" }));
-            }
-        }
-    }
-    payload
-}
-
 fn parse_custom_headers(headers_str: String) -> HashMap<String, String> {
     let mut headers = HashMap::new();
     for line in headers_str.lines() {
diff --git a/crates/goose/src/providers/openrouter.rs b/crates/goose/src/providers/openrouter.rs
index b3a679f423..01e1c9bc96 100644
--- a/crates/goose/src/providers/openrouter.rs
+++ b/crates/goose/src/providers/openrouter.rs
@@ -11,6 +11,7 @@ use super::openai_compatible::{handle_status, stream_openai_compat};
 use super::retry::ProviderRetry;
 use crate::conversation::message::Message;
 use crate::providers::formats::openrouter as openrouter_format;
+use goose_providers::cache_semantics::{apply_chat_payload_breakpoints, CacheSemantics};
 use goose_providers::errors::ProviderError;
 use goose_providers::formats::openai::create_request;
 use goose_providers::model::ModelConfig;
@@ -21,7 +22,6 @@ pub const OPENROUTER_PROVIDER_NAME: &str = "openrouter";
 const OPENROUTER_PARAMETERS_CONFIG_KEY: &str = "OPENROUTER_PARAMETERS";
 pub const OPENROUTER_DEFAULT_MODEL: &str = "anthropic/claude-sonnet-4";
 pub const OPENROUTER_DEFAULT_FAST_MODEL: &str = "google/gemini-2.5-flash";
-pub const OPENROUTER_MODEL_PREFIX_ANTHROPIC: &str = "anthropic";
 
 // OpenRouter can run many models, we suggest the default
 pub const OPENROUTER_KNOWN_MODELS: &[&str] = &[
@@ -98,79 +98,6 @@ fn is_mandatory_reasoning_error(error: &ProviderError) -> bool {
     matches!(error, ProviderError::RequestFailed(message) if message.contains("Reasoning is mandatory"))
 }
 
-/// Update the request when using anthropic model.
-/// For anthropic model, we can enable prompt caching to save cost. Since openrouter is the OpenAI compatible
-/// endpoint, we need to modify the open ai request to have anthropic cache control field.
-fn update_request_for_anthropic(original_payload: &Value) -> Value {
-    let mut payload = original_payload.clone();
-
-    if let Some(messages_spec) = payload
-        .as_object_mut()
-        .and_then(|obj| obj.get_mut("messages"))
-        .and_then(|messages| messages.as_array_mut())
-    {
-        // Add "cache_control" to the last and second-to-last "user" messages.
-        // During each turn, we mark the final message with cache_control so the conversation can be
-        // incrementally cached. The second-to-last user message is also marked for caching with the
-        // cache_control parameter, so that this checkpoint can read from the previous cache.
-        let mut user_count = 0;
-        for message in messages_spec.iter_mut().rev() {
-            if message.get("role") == Some(&json!("user")) {
-                if let Some(content) = message.get_mut("content") {
-                    if let Some(content_str) = content.as_str() {
-                        *content = json!([{
-                            "type": "text",
-                            "text": content_str,
-                            "cache_control": { "type": "ephemeral" }
-                        }]);
-                    }
-                }
-                user_count += 1;
-                if user_count >= 2 {
-                    break;
-                }
-            }
-        }
-
-        // Update the system message to have cache_control field.
-        if let Some(system_message) = messages_spec
-            .iter_mut()
-            .find(|msg| msg.get("role") == Some(&json!("system")))
-        {
-            if let Some(content) = system_message.get_mut("content") {
-                if let Some(content_str) = content.as_str() {
-                    *system_message = json!({
-                        "role": "system",
-                        "content": [{
-                            "type": "text",
-                            "text": content_str,
-                            "cache_control": { "type": "ephemeral" }
-                        }]
-                    });
-                }
-            }
-        }
-    }
-
-    if let Some(tools_spec) = payload
-        .as_object_mut()
-        .and_then(|obj| obj.get_mut("tools"))
-        .and_then(|tools| tools.as_array_mut())
-    {
-        // Add "cache_control" to the last tool spec, if any. This means that all tool definitions,
-        // will be cached as a single prefix.
-        if let Some(last_tool) = tools_spec.last_mut() {
-            if let Some(function) = last_tool.get_mut("function") {
-                function
-                    .as_object_mut()
-                    .unwrap()
-                    .insert("cache_control".to_string(), json!({ "type": "ephemeral" }));
-            }
-        }
-    }
-    payload
-}
-
 fn is_gemini_model(model_name: &str) -> bool {
     model_name.starts_with("google/")
 }
@@ -350,8 +277,10 @@ impl Provider for OpenRouterProvider {
             }
         }
 
-        if supports_cache_control(model_config) {
-            payload = update_request_for_anthropic(&payload);
+        if CacheSemantics::for_model(OPENROUTER_PROVIDER_NAME, &model_config.model_name)
+            .uses_explicit_breakpoints()
+        {
+            apply_chat_payload_breakpoints(&mut payload);
         }
 
         if is_gemini_model(&model_config.model_name) {
@@ -386,12 +315,6 @@ impl Provider for OpenRouterProvider {
     }
 }
 
-fn supports_cache_control(model: &ModelConfig) -> bool {
-    model
-        .model_name
-        .starts_with(OPENROUTER_MODEL_PREFIX_ANTHROPIC)
-}
-
 #[cfg(test)]
 mod tests {
     use super::*;
diff --git a/crates/goose/src/scheduler.rs b/crates/goose/src/scheduler.rs
index 23914b98c7..ed9dad2f3c 100644
--- a/crates/goose/src/scheduler.rs
+++ b/crates/goose/src/scheduler.rs
@@ -1493,7 +1493,13 @@ mod tests {
             .unwrap();
         assert_eq!(
             sessions[0].message_count,
-            session.conversation.unwrap().messages().len()
+            session
+                .conversation
+                .unwrap()
+                .messages()
+                .iter()
+                .filter(|m| m.is_user_visible())
+                .count()
         );
     }
 
diff --git a/crates/goose/src/security/adversary_inspector.rs b/crates/goose/src/security/adversary_inspector.rs
index 23881d9e27..49bf010823 100644
--- a/crates/goose/src/security/adversary_inspector.rs
+++ b/crates/goose/src/security/adversary_inspector.rs
@@ -224,7 +224,7 @@ impl AdversaryInspector {
         messages
             .iter()
             .rev()
-            .filter(|m| m.role == rmcp::model::Role::User)
+            .filter(|m| m.role == rmcp::model::Role::User && !m.is_turn_context())
             .filter_map(|m| {
                 let text: String = m
                     .content
@@ -250,7 +250,7 @@ impl AdversaryInspector {
 
     fn extract_original_task(messages: &[Message]) -> String {
         for msg in messages {
-            if msg.role == rmcp::model::Role::User {
+            if msg.role == rmcp::model::Role::User && !msg.is_turn_context() {
                 let text: String = msg
                     .content
                     .iter()
@@ -720,4 +720,39 @@ mod tests {
             .unwrap();
         assert!(results.is_empty());
     }
+
+    #[test]
+    fn user_context_extraction_skips_turn_context_events() {
+        use crate::conversation::message::MessageMetadata;
+
+        let turn_context = |text: &str| {
+            Message::user()
+                .with_text(text)
+                .with_metadata(MessageMetadata::agent_only().with_turn_context())
+        };
+        let messages = vec![
+            turn_context("turn context before any prompt"),
+            Message::user().with_text("never delete files outside the repo"),
+            turn_context("turn context for turn one"),
+            Message::assistant().with_text("understood"),
+            Message::user().with_text("first task"),
+            turn_context("turn context for turn two"),
+            Message::assistant().with_text("done"),
+            Message::user().with_text("second task"),
+            turn_context("turn context for turn three"),
+        ];
+
+        let recent = AdversaryInspector::extract_recent_user_messages(&messages, 4);
+        assert_eq!(
+            recent,
+            vec![
+                "never delete files outside the repo",
+                "first task",
+                "second task"
+            ]
+        );
+
+        let original = AdversaryInspector::extract_original_task(&messages);
+        assert_eq!(original, "never delete files outside the repo");
+    }
 }
diff --git a/crates/goose/src/security/scanner.rs b/crates/goose/src/security/scanner.rs
index 5483e76c2a..ef24e3cc42 100644
--- a/crates/goose/src/security/scanner.rs
+++ b/crates/goose/src/security/scanner.rs
@@ -354,6 +354,7 @@ impl PromptInjectionScanner {
             .rev()
             .filter(|m| {
                 crate::conversation::effective_role(m) == crate::conversation::EffectiveRole::User
+                    && !m.is_turn_context()
             })
             .take(limit)
             .map(|m| {
@@ -460,4 +461,33 @@ mod tests {
 
         assert!(result.is_malicious);
     }
+
+    #[test]
+    fn extract_user_messages_skips_turn_context_events() {
+        use crate::conversation::message::MessageMetadata;
+
+        let scanner = PromptInjectionScanner::new();
+        let turn_context = |text: &str| {
+            Message::user()
+                .with_text(text)
+                .with_metadata(MessageMetadata::agent_only().with_turn_context())
+        };
+        let messages = vec![
+            Message::user().with_text("oldest prompt"),
+            turn_context("turn context one"),
+            Message::assistant().with_text("ok"),
+            Message::user().with_text("middle prompt"),
+            turn_context("turn context two"),
+            Message::assistant().with_text("done"),
+            Message::user().with_text("newest prompt"),
+            turn_context("turn context three"),
+        ];
+
+        let extracted = scanner.extract_user_messages(&messages, 3);
+
+        assert_eq!(
+            extracted,
+            vec!["newest prompt", "middle prompt", "oldest prompt"]
+        );
+    }
 }
diff --git a/crates/goose/src/session/chat_history_search.rs b/crates/goose/src/session/chat_history_search.rs
index 3de7c628a0..a92768a334 100644
--- a/crates/goose/src/session/chat_history_search.rs
+++ b/crates/goose/src/session/chat_history_search.rs
@@ -150,6 +150,13 @@ impl<'a> ChatHistorySearch<'a> {
                 END,
                 1
             ) = 1
+            AND COALESCE(
+                CASE
+                    WHEN json_valid(m.metadata_json)
+                    THEN json_extract(m.metadata_json, '$.turnContext')
+                END,
+                0
+            ) = 0
             AND EXISTS (
                 SELECT 1 FROM json_each(m.content_json) AS content
                 WHERE json_extract(content.value, '$.type') = 'text'
@@ -263,12 +270,29 @@ impl<'a> ChatHistorySearch<'a> {
     ) -> Result<HashMap<String, usize>> {
         let mut session_totals: HashMap<String, usize> = HashMap::new();
         for session_id in session_messages.keys() {
-            let count: i64 =
-                sqlx::query_scalar("SELECT COUNT(*) FROM messages WHERE session_id = ?")
-                    .bind(session_id)
-                    .fetch_one(self.pool)
-                    .await
-                    .unwrap_or(0);
+            let count: i64 = sqlx::query_scalar(
+                r#"
+                SELECT COUNT(*) FROM messages m WHERE m.session_id = ?
+                AND COALESCE(
+                    CASE
+                        WHEN json_valid(m.metadata_json)
+                        THEN json_extract(m.metadata_json, '$.agentVisible')
+                    END,
+                    1
+                ) = 1
+                AND COALESCE(
+                    CASE
+                        WHEN json_valid(m.metadata_json)
+                        THEN json_extract(m.metadata_json, '$.turnContext')
+                    END,
+                    0
+                ) = 0
+                "#,
+            )
+            .bind(session_id)
+            .fetch_one(self.pool)
+            .await
+            .unwrap_or(0);
             session_totals.insert(session_id.clone(), count as usize);
         }
         Ok(session_totals)
@@ -443,5 +467,26 @@ mod tests {
                 .await
                 .unwrap();
         assert_eq!(hidden_only.total_matches, 0);
+
+        insert_message(
+            &pool,
+            &Message::user()
+                .with_text("<turn-context>needle in operational context</turn-context>")
+                .with_metadata(MessageMetadata::agent_only().with_turn_context()),
+            now,
+        )
+        .await;
+        let needle = ChatHistorySearch::new(&pool, "needle", Some(10), None, None, None, vec![])
+            .execute()
+            .await
+            .unwrap();
+        assert_eq!(
+            needle.total_matches, 1,
+            "turn-context events are operational context, not searchable conversation"
+        );
+        assert_eq!(
+            needle.results[0].total_messages_in_session, 2,
+            "session totals must not count turn-context or user-only rows"
+        );
     }
 }
diff --git a/crates/goose/src/session/session_manager.rs b/crates/goose/src/session/session_manager.rs
index 6cf6f285eb..77cf36e3cc 100644
--- a/crates/goose/src/session/session_manager.rs
+++ b/crates/goose/src/session/session_manager.rs
@@ -365,12 +365,14 @@ fn message_keyword_clause(keyword_count: usize) -> String {
         .collect::<Vec<_>>()
         .join(" OR ");
 
+    let visible = user_visible_message_sql("mq.metadata_json");
     format!(
         r#"
         EXISTS (
             SELECT 1
             FROM messages mq
             WHERE mq.session_id = s.id
+              AND {visible}
               AND EXISTS (
                   SELECT 1
                   FROM json_each(mq.content_json)
@@ -619,7 +621,7 @@ impl SessionManager {
         let user_message_count = conversation
             .messages()
             .iter()
-            .filter(|m| matches!(m.role, Role::User))
+            .filter(|m| matches!(m.role, Role::User) && m.is_user_visible())
             .count();
 
         let should_generate_name = if provider.manages_own_context() {
@@ -714,6 +716,10 @@ fn normalized_message_timestamp_sql(column: &str) -> String {
     )
 }
 
+fn user_visible_message_sql(column: &str) -> String {
+    format!("COALESCE(json_extract({column}, '$.userVisible'), 1) != 0")
+}
+
 fn session_sort_at(session: &Session) -> DateTime<Utc> {
     session.last_message_at.unwrap_or(session.updated_at)
 }
@@ -1629,7 +1635,11 @@ impl SessionStorage {
 
         if include_messages {
             let conv = self.get_conversation(&session.id).await?;
-            session.message_count = conv.messages().len();
+            session.message_count = conv
+                .messages()
+                .iter()
+                .filter(|m| m.is_user_visible())
+                .count();
             session.last_message_at = conv
                 .messages()
                 .iter()
@@ -1638,7 +1648,8 @@ impl SessionStorage {
             session.conversation = Some(conv);
         } else {
             let sql = format!(
-                "SELECT COUNT(*), MAX({}) FROM messages WHERE session_id = ?",
+                "SELECT COUNT(*) FILTER (WHERE {}), MAX({}) FROM messages WHERE session_id = ?",
+                user_visible_message_sql("metadata_json"),
                 normalized_message_timestamp_sql("created_timestamp")
             );
             let (count, last_message_timestamp): (i64, Option<i64>) = sqlx::query_as(&sql)
@@ -1979,7 +1990,7 @@ impl SessionStorage {
                    s.schedule_id, s.recipe_json, s.user_recipe_values_json,
                    s.provider_name, s.model_config_json, s.goose_mode,
                    s.archived_at, s.project_id, s.parent_session_id,
-                   COUNT(m.id) as message_count,
+                   COUNT(m.id) FILTER (WHERE {}) as message_count,
                    MAX({}) as last_message_timestamp,
                    {} as sort_timestamp
             FROM sessions s
@@ -1990,6 +2001,7 @@ impl SessionStorage {
             {}
             {}
             "#,
+            user_visible_message_sql("m.metadata_json"),
             normalized_message_timestamp,
             sort_timestamp_sql,
             message_join,
@@ -2985,6 +2997,44 @@ mod tests {
         assert_eq!(with_messages.last_message_at, Some(expected));
     }
 
+    #[tokio::test]
+    async fn test_message_count_excludes_agent_only_messages() {
+        let temp_dir = TempDir::new().unwrap();
+        let sm = SessionManager::new(temp_dir.path().to_path_buf());
+        let session = sm
+            .create_session(
+                PathBuf::from("/tmp/test"),
+                "Hidden events".to_string(),
+                SessionType::User,
+                GooseMode::default(),
+            )
+            .await
+            .unwrap();
+
+        add_user_message(&sm, &session.id).await;
+        sm.add_message(
+            &session.id,
+            &Message::user()
+                .with_text("<turn-context>frozen</turn-context>")
+                .with_visibility(false, true),
+        )
+        .await
+        .unwrap();
+        sm.add_message(&session.id, &Message::assistant().with_text("hi"))
+            .await
+            .unwrap();
+
+        let counted = sm.get_session(&session.id, false).await.unwrap();
+        assert_eq!(counted.message_count, 2);
+
+        let with_messages = sm.get_session(&session.id, true).await.unwrap();
+        assert_eq!(with_messages.message_count, 2);
+
+        let listed = sm.list_sessions().await.unwrap();
+        let listed_session = listed.iter().find(|s| s.id == session.id).unwrap();
+        assert_eq!(listed_session.message_count, 2);
+    }
+
     #[tokio::test]
     async fn test_truncate_conversation_from_message_keeps_same_second_previous_rows() {
         let temp_dir = TempDir::new().unwrap();
diff --git a/crates/goose/src/session/session_naming.rs b/crates/goose/src/session/session_naming.rs
index f5130bb5de..4e0f34d3e1 100644
--- a/crates/goose/src/session/session_naming.rs
+++ b/crates/goose/src/session/session_naming.rs
@@ -75,7 +75,7 @@ fn extract_short_title(text: &str) -> String {
 fn get_initial_user_messages(messages: &Conversation) -> Vec<String> {
     messages
         .iter()
-        .filter(|m| m.role == rmcp::model::Role::User)
+        .filter(|m| m.role == rmcp::model::Role::User && m.is_user_visible())
         .take(MSG_COUNT_FOR_SESSION_NAME_GENERATION)
         .map(|m| {
             m.content
diff --git a/crates/goose/tests/agent.rs b/crates/goose/tests/agent.rs
index 0ab078db8f..5f52e9e3aa 100644
--- a/crates/goose/tests/agent.rs
+++ b/crates/goose/tests/agent.rs
@@ -1404,7 +1404,11 @@ mod tests {
                 .messages()
                 .to_vec();
 
-            let user_count = messages.iter().filter(|m| m.role == Role::User).count();
+            // Turn-context events are excluded; this test is about streaming deltas.
+            let user_count = messages
+                .iter()
+                .filter(|m| m.role == Role::User && m.is_user_visible())
+                .count();
             let asst_count = messages
                 .iter()
                 .filter(|m| m.role == Role::Assistant)
@@ -1453,7 +1457,10 @@ mod tests {
                 .messages()
                 .to_vec();
 
-            let user_count2 = messages2.iter().filter(|m| m.role == Role::User).count();
+            let user_count2 = messages2
+                .iter()
+                .filter(|m| m.role == Role::User && m.is_user_visible())
+                .count();
             let asst_count2 = messages2
                 .iter()
                 .filter(|m| m.role == Role::Assistant)
diff --git a/crates/goose/tests/compaction.rs b/crates/goose/tests/compaction.rs
index 5f92de7dcc..4d1b9132dc 100644
--- a/crates/goose/tests/compaction.rs
+++ b/crates/goose/tests/compaction.rs
@@ -320,7 +320,12 @@ fn assert_conversation_compacted(conversation: &Conversation) {
                 "Message after compaction at index {} should be agent visible",
                 idx
             );
-            if idx == continuation_end && matches!(msg.role, rmcp::model::Role::User) {
+            if msg.is_turn_context() {
+                assert!(
+                    !msg.is_user_visible(),
+                    "Carried turn-context event should be user-invisible"
+                );
+            } else if idx == continuation_end && matches!(msg.role, rmcp::model::Role::User) {
                 assert!(
                     !msg.is_user_visible(),
                     "Projected preserved user message should be user-invisible"