diff --git a/crates/goose/src/agents/agent.rs b/crates/goose/src/agents/agent.rs
index e4134dd79d..ff398f95d0 100644
--- a/crates/goose/src/agents/agent.rs
+++ b/crates/goose/src/agents/agent.rs
@@ -1550,6 +1550,16 @@ impl Agent {
                             );
                             break;
                         }
+                        Err(ref provider_err @ ProviderError::NetworkError(_)) => {
+                            crate::posthog::emit_error(provider_err.telemetry_type(), &provider_err.to_string());
+                            error!("Error: {}", provider_err);
+                            yield AgentEvent::Message(
+                                Message::assistant().with_text(
+                                    format!("{provider_err}\n\nPlease resend your message to try again.")
+                                )
+                            );
+                            break;
+                        }
                         Err(ref provider_err) => {
                             crate::posthog::emit_error(provider_err.telemetry_type(), &provider_err.to_string());
                             error!("Error: {}", provider_err);
diff --git a/crates/goose/src/providers/anthropic.rs b/crates/goose/src/providers/anthropic.rs
index 5e6613a57e..2748011178 100644
--- a/crates/goose/src/providers/anthropic.rs
+++ b/crates/goose/src/providers/anthropic.rs
@@ -16,6 +16,7 @@ use super::formats::anthropic::{
 };
 use super::openai_compatible::handle_status_openai_compat;
 use super::openai_compatible::map_http_error_to_provider_error;
+use super::retry::ProviderRetry;
 use crate::config::declarative_providers::DeclarativeProviderConfig;
 use crate::conversation::message::Message;
 use crate::model::ModelConfig;
@@ -226,19 +227,22 @@ impl Provider for AnthropicProvider {
             .unwrap()
             .insert("stream".to_string(), Value::Bool(true));
 
-        let mut request = self.api_client.request(Some(session_id), "v1/messages");
+        let conditional_headers = self.get_conditional_headers();
         let mut log = RequestLog::start(model_config, &payload)?;
 
-        for (key, value) in self.get_conditional_headers() {
-            request = request.header(key, value)?;
-        }
-
-        let resp = request.response_post(&payload).await.inspect_err(|e| {
-            let _ = log.error(e);
-        })?;
-        let response = handle_status_openai_compat(resp).await.inspect_err(|e| {
-            let _ = log.error(e);
-        })?;
+        let response = self
+            .with_retry(|| async {
+                let mut request = self.api_client.request(Some(session_id), "v1/messages");
+                for (key, value) in &conditional_headers {
+                    request = request.header(key, value)?;
+                }
+                let resp = request.response_post(&payload).await?;
+                handle_status_openai_compat(resp).await
+            })
+            .await
+            .inspect_err(|e| {
+                let _ = log.error(e);
+            })?;
 
         let stream = response.bytes_stream().map_err(io::Error::other);
 
diff --git a/crates/goose/src/providers/errors.rs b/crates/goose/src/providers/errors.rs
index 71a99bbefa..214a14837d 100644
--- a/crates/goose/src/providers/errors.rs
+++ b/crates/goose/src/providers/errors.rs
@@ -19,6 +19,9 @@ pub enum ProviderError {
     #[error("Server error: {0}")]
     ServerError(String),
 
+    #[error("Network error: {0}")]
+    NetworkError(String),
+
     #[error("Request failed: {0}")]
     RequestFailed(String),
 
@@ -45,6 +48,7 @@ impl ProviderError {
             ProviderError::ContextLengthExceeded(_) => "context_length",
             ProviderError::RateLimitExceeded { .. } => "rate_limit",
             ProviderError::ServerError(_) => "server",
+            ProviderError::NetworkError(_) => "network",
             ProviderError::RequestFailed(_) => "request",
             ProviderError::ExecutionError(_) => "execution",
             ProviderError::UsageError(_) => "usage",
@@ -54,38 +58,51 @@ impl ProviderError {
     }
 }
 
+fn is_network_error(err: &reqwest::Error) -> bool {
+    err.is_connect() || err.is_timeout() || (err.status().is_none() && err.is_request())
+}
+
+fn provider_error_from_reqwest(error: &reqwest::Error) -> ProviderError {
+    if is_network_error(error) {
+        let msg = if error.is_timeout() {
+            "Request timed out — check your network connection and try again.".to_string()
+        } else if error.is_connect() {
+            if let Some(url) = error.url() {
+                if let Some(host) = url.host_str() {
+                    let port_info = url.port().map(|p| format!(":{}", p)).unwrap_or_default();
+                    format!(
+                        "Could not connect to {}{} — check your network connection and try again.",
+                        host, port_info
+                    )
+                } else {
+                    "Could not connect to the provider — check your network connection and try again.".to_string()
+                }
+            } else {
+                "Could not connect to the provider — check your network connection and try again."
+                    .to_string()
+            }
+        } else {
+            "Network error — check your network connection and try again.".to_string()
+        };
+        return ProviderError::NetworkError(msg);
+    }
+
+    let mut details = vec![];
+    if let Some(status) = error.status() {
+        details.push(format!("status: {}", status));
+    }
+    let msg = if details.is_empty() {
+        error.to_string()
+    } else {
+        format!("{} ({})", error, details.join(", "))
+    };
+    ProviderError::RequestFailed(msg)
+}
+
 impl From<anyhow::Error> for ProviderError {
     fn from(error: anyhow::Error) -> Self {
         if let Some(reqwest_err) = error.downcast_ref::<reqwest::Error>() {
-            let mut details = vec![];
-
-            if let Some(status) = reqwest_err.status() {
-                details.push(format!("status: {}", status));
-            }
-            if reqwest_err.is_timeout() {
-                details.push("timeout".to_string());
-            }
-            if reqwest_err.is_connect() {
-                if let Some(url) = reqwest_err.url() {
-                    if let Some(host) = url.host_str() {
-                        let port_info = url.port().map(|p| format!(":{}", p)).unwrap_or_default();
-
-                        details.push(format!("failed to connect to {}{}", host, port_info));
-
-                        if url.port().is_some() {
-                            details.push("check that the port is correct".to_string());
-                        }
-                    }
-                } else {
-                    details.push("connection failed".to_string());
-                }
-            }
-            let msg = if details.is_empty() {
-                reqwest_err.to_string()
-            } else {
-                format!("{} ({})", reqwest_err, details.join(", "))
-            };
-            return ProviderError::RequestFailed(msg);
+            return provider_error_from_reqwest(reqwest_err);
         }
         ProviderError::ExecutionError(error.to_string())
     }
@@ -93,7 +110,7 @@ impl From<anyhow::Error> for ProviderError {
 
 impl From<reqwest::Error> for ProviderError {
     fn from(error: reqwest::Error) -> Self {
-        ProviderError::RequestFailed(error.to_string())
+        provider_error_from_reqwest(&error)
     }
 }
 
diff --git a/crates/goose/src/providers/retry.rs b/crates/goose/src/providers/retry.rs
index ca1a6f7261..4a8a17a92f 100644
--- a/crates/goose/src/providers/retry.rs
+++ b/crates/goose/src/providers/retry.rs
@@ -76,6 +76,7 @@ pub fn should_retry(error: &ProviderError) -> bool {
         error,
         ProviderError::RateLimitExceeded { .. }
             | ProviderError::ServerError(_)
+            | ProviderError::NetworkError(_)
             | ProviderError::RequestFailed(_)
     )
 }