diff --git a/surfsense_backend/app/agents/chat/multi_agent_chat/main_agent/middleware/checkpointed_subagent_middleware/resume_routing.py b/surfsense_backend/app/agents/chat/multi_agent_chat/main_agent/middleware/checkpointed_subagent_middleware/resume_routing.py
index 37f45e42f..d3a85c1dc 100644
--- a/surfsense_backend/app/agents/chat/multi_agent_chat/main_agent/middleware/checkpointed_subagent_middleware/resume_routing.py
+++ b/surfsense_backend/app/agents/chat/multi_agent_chat/main_agent/middleware/checkpointed_subagent_middleware/resume_routing.py
@@ -34,23 +34,13 @@ def slice_decisions_by_tool_call(
 ) -> dict[str, dict[str, Any]]:
     """Slice ``decisions`` into ``{tool_call_id: {"decisions": <slice>}}``.
 
-    Args:
-        decisions: Flat list of decisions in the order the SSE stream rendered
-            them.
-        pending: Ordered ``(tool_call_id, action_count)`` pairs in the same
-            order. The slicer consumes ``decisions`` left-to-right.
-
-    Returns:
-        Per-``tool_call_id`` payload dict ready to be written to
-        ``configurable["surfsense_resume_value"]``.
-
-    Raises:
-        ValueError: When the total expected action count differs from the
-            number of decisions provided. We fail loud rather than silently
-            dropping or padding so a frontend/backend contract drift surfaces
-            immediately.
+    Routes by identity when every decision carries a ``tool_call_id``, else by
+    position in ``pending`` order. Raises on any count or id mismatch.
     """
     pending_list = list(pending)
+    if decisions and all(d.get("tool_call_id") for d in decisions):
+        return _route_by_id(decisions, pending_list)
+
     expected = sum(count for _, count in pending_list)
     if expected != len(decisions):
         raise ValueError(
@@ -66,6 +56,34 @@ def slice_decisions_by_tool_call(
     return routed
 
 
+def _route_by_id(
+    decisions: list[dict[str, Any]],
+    pending_list: list[tuple[str, int]],
+) -> dict[str, dict[str, Any]]:
+    """Route id-stamped decisions to their pending tool call, validating identity."""
+    grouped: dict[str, list[dict[str, Any]]] = {}
+    for decision in decisions:
+        grouped.setdefault(str(decision["tool_call_id"]), []).append(decision)
+
+    pending_ids = {tool_call_id for tool_call_id, _ in pending_list}
+    if set(grouped) != pending_ids:
+        raise ValueError(
+            "Decision routing mismatch: decisions target "
+            f"{sorted(grouped)} but pending tool calls are {sorted(pending_ids)}."
+        )
+
+    routed: dict[str, dict[str, Any]] = {}
+    for tool_call_id, action_count in pending_list:
+        slice_ = grouped[tool_call_id]
+        if len(slice_) != action_count:
+            raise ValueError(
+                f"Decision count mismatch for tool_call_id={tool_call_id!r}: "
+                f"expected {action_count} action(s) but received {len(slice_)}."
+            )
+        routed[tool_call_id] = {"decisions": slice_}
+    return routed
+
+
 def collect_pending_tool_calls(state: Any) -> list[tuple[str, int]]:
     """Extract ``[(tool_call_id, action_count), ...]`` from a paused parent state.
 
@@ -138,6 +156,61 @@ def collect_pending_tool_calls(state: Any) -> list[tuple[str, int]]:
     return pending
 
 
+def collect_pending_parent_interrupts(state: Any) -> list[tuple[str, int]]:
+    """Ordered ``(interrupt_id, action_count)`` for unstamped parent-graph interrupts.
+
+    Complements :func:`collect_pending_tool_calls`: main-agent
+    ``PermissionMiddleware`` asks and ``DoomLoopMiddleware`` pauses carry no
+    ``tool_call_id`` (they never cross a ``task`` call), so they must be routed
+    by ``Interrupt.id`` instead. ``action_count`` defaults to 1 for scalar
+    payloads (e.g. doom-loop) with no ``action_requests``.
+    """
+    pending: list[tuple[str, int]] = []
+    for interrupt_obj in getattr(state, "interrupts", ()) or ():
+        value = getattr(interrupt_obj, "value", None)
+        if not isinstance(value, dict):
+            continue
+        if isinstance(value.get("tool_call_id"), str):
+            continue  # subagent-routed; owned by collect_pending_tool_calls
+        interrupt_id = getattr(interrupt_obj, "id", None)
+        if not isinstance(interrupt_id, str):
+            continue
+        action_requests = value.get("action_requests")
+        count = (
+            len(action_requests)
+            if isinstance(action_requests, list) and action_requests
+            else 1
+        )
+        pending.append((interrupt_id, count))
+    return pending
+
+
+def build_parent_resume_map(
+    decisions: list[dict[str, Any]],
+    parent_pending: list[tuple[str, int]],
+) -> dict[str, Any]:
+    """Map ``Interrupt.id → resume_value`` for parent-side interrupts.
+
+    Single-action asks deliver the raw decision dict (the site's
+    ``interrupt()`` return); parent sites read it directly and never unwrap a
+    ``{"decisions": [...]}`` bundle. Raises on a decision-count mismatch.
+    """
+    expected = sum(count for _, count in parent_pending)
+    if expected != len(decisions):
+        raise ValueError(
+            f"Decision count mismatch: parent-side interrupts expect "
+            f"{expected} actions but received {len(decisions)} decisions."
+        )
+
+    out: dict[str, Any] = {}
+    cursor = 0
+    for interrupt_id, count in parent_pending:
+        chunk = decisions[cursor : cursor + count]
+        cursor += count
+        out[interrupt_id] = chunk[0] if count == 1 else {"decisions": chunk}
+    return out
+
+
 def build_lg_resume_map(
     state: Any, by_tool_call_id: dict[str, dict[str, Any]]
 ) -> dict[str, dict[str, Any]]:
diff --git a/surfsense_backend/app/agents/chat/multi_agent_chat/main_agent/middleware/checkpointed_subagent_middleware/task_tool.py b/surfsense_backend/app/agents/chat/multi_agent_chat/main_agent/middleware/checkpointed_subagent_middleware/task_tool.py
index cc5ebaa98..f0e0e25c1 100644
--- a/surfsense_backend/app/agents/chat/multi_agent_chat/main_agent/middleware/checkpointed_subagent_middleware/task_tool.py
+++ b/surfsense_backend/app/agents/chat/multi_agent_chat/main_agent/middleware/checkpointed_subagent_middleware/task_tool.py
@@ -13,15 +13,15 @@ import json
 import logging
 import time
 from collections.abc import Awaitable, Callable
-from typing import Annotated, Any, NoReturn, TypeVar
+from typing import Annotated, Any, Literal, NoReturn, TypeVar
 
-from deepagents.middleware.subagents import TASK_TOOL_DESCRIPTION
 from langchain.tools import BaseTool, ToolRuntime
 from langchain_core.messages import HumanMessage, ToolMessage
 from langchain_core.runnables import Runnable
 from langchain_core.tools import StructuredTool
 from langgraph.errors import GraphInterrupt
 from langgraph.types import Command, Interrupt
+from pydantic import ConfigDict, Field, create_model, field_validator
 
 from app.agents.chat.multi_agent_chat.constants import LEGACY_SUBAGENT_ALIASES
 from app.agents.chat.multi_agent_chat.subagents.shared.invocation import (
@@ -58,6 +58,24 @@ from .spawn_paused import is_spawn_paused
 logger = logging.getLogger(__name__)
 _perf_log = get_perf_logger()
 
+_DEFAULT_TASK_DESCRIPTION = (
+    "Invoke a specialist subagent: pass its `subagent_type` and a full "
+    "`description` of the task. See the `<specialists>` roster for who exists."
+)
+
+_MISSING_RUNTIME_ERROR = (
+    "task: could not read the tool runtime for this call (likely a truncated or "
+    "malformed tool call). Re-issue the task with a complete `description` and "
+    "`subagent_type`."
+)
+
+
+def _runtime_error(runtime: ToolRuntime | None) -> str | None:
+    """Model-readable error string if no usable runtime was injected, else ``None``."""
+    if runtime is None or not getattr(runtime, "tool_call_id", None):
+        return _MISSING_RUNTIME_ERROR
+    return None
+
 
 class SubagentInvokeTimeoutError(Exception):
     """Raised when ``subagent.ainvoke`` exceeds the configured wall-clock budget.
@@ -194,18 +212,7 @@ def build_task_tool_with_parent_config(
         for spec in subagents
         if (provider := spec.get(SURF_CONTEXT_HINT_PROVIDER_KEY)) is not None
     }
-    subagent_description_str = "\n".join(
-        f"- {s['name']}: {s['description']}" for s in subagents
-    )
-
-    if task_description is None:
-        description = TASK_TOOL_DESCRIPTION.format(
-            available_agents=subagent_description_str
-        )
-    elif "{available_agents}" in task_description:
-        description = task_description.format(available_agents=subagent_description_str)
-    else:
-        description = task_description
+    description = task_description or _DEFAULT_TASK_DESCRIPTION
 
     def _billable_call_update(
         subagent_type: str, runtime: ToolRuntime
@@ -669,6 +676,8 @@ def build_task_tool_with_parent_config(
             ),
         ] = None,
     ) -> str | Command:
+        if (err := _runtime_error(runtime)) is not None:
+            return err
         if tasks is not None:
             return (
                 "task: batch mode (`tasks=[...]`) is only supported on the async "
@@ -687,8 +696,6 @@ def build_task_tool_with_parent_config(
                 f"We cannot invoke subagent {subagent_type} because it does not exist, "
                 f"the only allowed types are {allowed_types}"
             )
-        if not runtime.tool_call_id:
-            raise ValueError("Tool call ID is required for subagent invocation")
         subagent, subagent_state = _validate_and_prepare_state(
             subagent_type, description, runtime
         )
@@ -850,6 +857,8 @@ def build_task_tool_with_parent_config(
         ] = None,
     ) -> str | Command:
         atask_start = time.perf_counter()
+        if (err := _runtime_error(runtime)) is not None:
+            return err
         # Ops kill switch: short-circuit every task() call for this workspace
         # so the orchestrator stops hammering downstream APIs.
         if await is_spawn_paused(workspace_id):
@@ -869,8 +878,6 @@ def build_task_tool_with_parent_config(
                     "task: cannot combine `tasks` with `description`/`subagent_type`. "
                     "Use either single-mode (description+subagent_type) or batch-mode (tasks)."
                 )
-            if not runtime.tool_call_id:
-                raise ValueError("Tool call ID is required for subagent invocation")
             coerced = _coerce_batch_arg(tasks)
             if isinstance(coerced, str):
                 return coerced
@@ -897,8 +904,6 @@ def build_task_tool_with_parent_config(
                 f"We cannot invoke subagent {subagent_type} because it does not exist, "
                 f"the only allowed types are {allowed_types}"
             )
-        if not runtime.tool_call_id:
-            raise ValueError("Tool call ID is required for subagent invocation")
         subagent, subagent_state = _validate_and_prepare_state(
             subagent_type, description, runtime
         )
@@ -1130,4 +1135,72 @@ def build_task_tool_with_parent_config(
         func=task,
         coroutine=atask,
         description=description,
+        args_schema=_build_task_args_schema(subagent_names),
+        handle_validation_error=_on_invalid_task_args(subagent_names),
     )
+
+
+def _build_task_args_schema(subagent_names: set[str]) -> type:
+    """Args schema constraining single-mode ``subagent_type`` to the live roster.
+
+    The ``Literal`` surfaces the roster as a provider-side enum. A before-validator
+    rewrites legacy connector aliases onto their consolidated route so paused
+    pre-consolidation checkpoints still resolve; the aliases stay out of the enum.
+    """
+    roster = sorted(subagent_names)
+
+    def _canonicalize_legacy(cls, value):
+        if isinstance(value, str) and value not in subagent_names:
+            return LEGACY_SUBAGENT_ALIASES.get(value, value)
+        return value
+
+    return create_model(
+        "TaskToolArgs",
+        __config__=ConfigDict(arbitrary_types_allowed=True),
+        __validators__={
+            "_canonicalize_legacy_subagent_type": field_validator(
+                "subagent_type", mode="before"
+            )(_canonicalize_legacy)
+        },
+        # ``runtime`` is injected by ToolNode; it must be a declared field or
+        # validation drops it (ToolRuntime is directly-injected, so it is not in
+        # ``_injected_args_keys``). Bare ``ToolRuntime`` (not a Union) so
+        # ``_is_directly_injected_arg_type`` keeps it out of the model-facing schema.
+        runtime=(ToolRuntime, Field(default=None)),
+        description=(
+            str | None,
+            Field(
+                default=None,
+                description="Single-mode: full task prompt. Required unless `tasks` is provided.",
+            ),
+        ),
+        subagent_type=(
+            Literal[tuple(roster)] | None if roster else str | None,
+            Field(
+                default=None,
+                description="Single-mode: which specialist to invoke. Required unless `tasks` is provided.",
+            ),
+        ),
+        tasks=(
+            list[dict] | None,
+            Field(
+                default=None,
+                description=(
+                    "Batch-mode: array of `{description, subagent_type}` objects to "
+                    "fan out concurrently. Mutually exclusive with single-mode args."
+                ),
+            ),
+        ),
+    )
+
+
+def _on_invalid_task_args(subagent_names: set[str]) -> Callable[[Exception], str]:
+    allowed = ", ".join(f"`{n}`" for n in sorted(subagent_names))
+
+    def _handle(_exc: Exception) -> str:
+        return (
+            f"Invalid `task` arguments. `subagent_type` must be one of: {allowed}. "
+            "For batch mode send `tasks=[{description, subagent_type}, ...]`."
+        )
+
+    return _handle
diff --git a/surfsense_backend/app/agents/chat/multi_agent_chat/main_agent/middleware/continue_on_max_length.py b/surfsense_backend/app/agents/chat/multi_agent_chat/main_agent/middleware/continue_on_max_length.py
new file mode 100644
index 000000000..daf67aad2
--- /dev/null
+++ b/surfsense_backend/app/agents/chat/multi_agent_chat/main_agent/middleware/continue_on_max_length.py
@@ -0,0 +1,190 @@
+"""Auto-continue a final text answer cut off by ``max_tokens``.
+
+``langchain_litellm`` drops ``finish_reason`` from streamed chunks, so a
+token-limit cut would otherwise reach the user as a silent stub. When the last
+message is a tool-call-free text answer that hit its output cap, re-invoke with
+the partial prefilled and stitch the pieces until it finishes. Tool-call
+truncation (invalid partial JSON) and non-string content fall back to the
+usage-based truncation marker.
+"""
+
+from __future__ import annotations
+
+import dataclasses
+from typing import TYPE_CHECKING, Any
+
+from langchain.agents.middleware import AgentMiddleware
+from langchain_core.messages import AIMessage, BaseMessage, HumanMessage
+
+from app.services.token_tracking_service import (
+    get_current_accumulator,
+    is_output_truncated,
+)
+
+if TYPE_CHECKING:
+    from collections.abc import Awaitable, Callable
+
+_CONTINUE_NUDGE = HumanMessage(
+    content=(
+        "Your previous response was cut off before it finished. Continue exactly "
+        "where you left off. Do not repeat any text you already wrote and do not "
+        "add any preamble."
+    )
+)
+
+
+def _final_text_ai(response: Any) -> AIMessage | None:
+    result = getattr(response, "result", None) or []
+    msg = result[-1] if result else None
+    return msg if isinstance(msg, AIMessage) else None
+
+
+def _plain_text(ai: AIMessage) -> str | None:
+    return ai.content if isinstance(ai.content, str) else None
+
+
+def _output_tokens(ai: AIMessage) -> int:
+    return (ai.usage_metadata or {}).get("output_tokens", 0) or 0
+
+
+def _finish_reason(ai: AIMessage) -> str | None:
+    return (ai.response_metadata or {}).get("finish_reason")
+
+
+def _model_max_tokens(request: Any) -> int | None:
+    return getattr(getattr(request, "model", None), "max_tokens", None)
+
+
+def _continuation_messages(base: list[BaseMessage], accumulated: str) -> list[BaseMessage]:
+    return [*base, AIMessage(content=accumulated), _CONTINUE_NUDGE]
+
+
+def _merge(first_ai: AIMessage, text: str, total_out: int) -> AIMessage:
+    usage = dict(first_ai.usage_metadata or {})
+    if usage:
+        usage["output_tokens"] = total_out
+        usage["total_tokens"] = usage.get("input_tokens", 0) + total_out
+    metadata = dict(first_ai.response_metadata or {})
+    metadata["finish_reason"] = "stop"
+    return AIMessage(
+        content=text,
+        id=first_ai.id,
+        usage_metadata=usage or None,
+        response_metadata=metadata,
+        additional_kwargs=first_ai.additional_kwargs,
+    )
+
+
+class ContinueOnMaxLengthMiddleware(AgentMiddleware):  # type: ignore[type-arg]
+    """Stitch continuations onto a truncated, tool-call-free text answer."""
+
+    def __init__(self, max_continuations: int = 2) -> None:
+        super().__init__()
+        self.max_continuations = max_continuations
+
+    def _should_continue(self, ai: AIMessage, max_tokens: int | None) -> bool:
+        return not ai.tool_calls and is_output_truncated(
+            _finish_reason(ai), _output_tokens(ai), max_tokens
+        )
+
+    def _finalize(
+        self,
+        *,
+        response: Any,
+        last_response: Any,
+        first_ai: AIMessage,
+        ai: AIMessage | None,
+        accumulated: str,
+        total_out: int,
+        done: int,
+        max_tokens: int | None,
+    ) -> Any:
+        if done == 0:
+            return response
+        # Recovered a complete answer: the per-call ``length`` the token callback
+        # flagged is no longer user-visible, so clear the marker.
+        if ai is not None and not self._should_continue(ai, max_tokens):
+            acc = get_current_accumulator()
+            if acc is not None:
+                acc.truncated = False
+        return dataclasses.replace(
+            last_response, result=[_merge(first_ai, accumulated, total_out)]
+        )
+
+    def wrap_model_call(  # type: ignore[override]
+        self,
+        request: Any,
+        handler: Callable[[Any], Any],
+    ) -> Any:
+        response = handler(request)
+        ai = _final_text_ai(response)
+        max_tokens = _model_max_tokens(request)
+        if ai is None or (accumulated := _plain_text(ai)) is None:
+            return response
+
+        total_out = _output_tokens(ai)
+        first_ai, last_response, done = ai, response, 0
+        while done < self.max_continuations and self._should_continue(ai, max_tokens):
+            done += 1
+            last_response = handler(
+                request.override(messages=_continuation_messages(request.messages, accumulated))
+            )
+            ai = _final_text_ai(last_response)
+            if ai is None or (piece := _plain_text(ai)) is None:
+                break
+            accumulated += piece
+            total_out += _output_tokens(ai)
+
+        return self._finalize(
+            response=response,
+            last_response=last_response,
+            first_ai=first_ai,
+            ai=ai,
+            accumulated=accumulated,
+            total_out=total_out,
+            done=done,
+            max_tokens=max_tokens,
+        )
+
+    async def awrap_model_call(  # type: ignore[override]
+        self,
+        request: Any,
+        handler: Callable[[Any], Awaitable[Any]],
+    ) -> Any:
+        response = await handler(request)
+        ai = _final_text_ai(response)
+        max_tokens = _model_max_tokens(request)
+        if ai is None or (accumulated := _plain_text(ai)) is None:
+            return response
+
+        total_out = _output_tokens(ai)
+        first_ai, last_response, done = ai, response, 0
+        while done < self.max_continuations and self._should_continue(ai, max_tokens):
+            done += 1
+            last_response = await handler(
+                request.override(messages=_continuation_messages(request.messages, accumulated))
+            )
+            ai = _final_text_ai(last_response)
+            if ai is None or (piece := _plain_text(ai)) is None:
+                break
+            accumulated += piece
+            total_out += _output_tokens(ai)
+
+        return self._finalize(
+            response=response,
+            last_response=last_response,
+            first_ai=first_ai,
+            ai=ai,
+            accumulated=accumulated,
+            total_out=total_out,
+            done=done,
+            max_tokens=max_tokens,
+        )
+
+
+def build_continue_on_max_length_mw(flags: Any) -> ContinueOnMaxLengthMiddleware | None:
+    from ...shared.middleware.flags import enabled
+
+    if not enabled(flags, "enable_continue_on_max_length"):
+        return None
+    return ContinueOnMaxLengthMiddleware(max_continuations=2)
diff --git a/surfsense_backend/app/agents/chat/multi_agent_chat/main_agent/middleware/doom_loop/middleware.py b/surfsense_backend/app/agents/chat/multi_agent_chat/main_agent/middleware/doom_loop/middleware.py
index 4f9b4af1c..2f3b1d17f 100644
--- a/surfsense_backend/app/agents/chat/multi_agent_chat/main_agent/middleware/doom_loop/middleware.py
+++ b/surfsense_backend/app/agents/chat/multi_agent_chat/main_agent/middleware/doom_loop/middleware.py
@@ -12,8 +12,9 @@ the agent has likely entered an infinite loop. We surface this to the
 user as an interrupt with ``permission="doom_loop"`` so the UI can
 render an "Are you stuck? Continue / cancel?" affordance.
 
-This ships **OFF by default** until the frontend explicitly handles
-``context.permission == "doom_loop"`` interrupts.
+Ships ON by default (``enable_doom_loop``): the frontend renders a dedicated
+continue/stop card for ``context.permission == "doom_loop"`` and the resume
+router routes the reply back by ``Interrupt.id``.
 
 Wire format: uses SurfSense's existing ``interrupt()`` payload shape
 (see ``app/agents/shared/tools/hitl.py``):
diff --git a/surfsense_backend/app/agents/chat/multi_agent_chat/main_agent/middleware/stack.py b/surfsense_backend/app/agents/chat/multi_agent_chat/main_agent/middleware/stack.py
index 0b6291804..a46f03477 100644
--- a/surfsense_backend/app/agents/chat/multi_agent_chat/main_agent/middleware/stack.py
+++ b/surfsense_backend/app/agents/chat/multi_agent_chat/main_agent/middleware/stack.py
@@ -85,6 +85,7 @@ from .checkpointed_subagent_middleware.task_description import (
     TASK_TOOL_DESCRIPTION,
 )
 from .context_editing import build_context_editing_mw
+from .continue_on_max_length import build_continue_on_max_length_mw
 from .dedup_hitl import build_dedup_hitl_mw
 from .doom_loop import build_doom_loop_mw
 from .kb_persistence import build_kb_persistence_mw
@@ -273,6 +274,7 @@ def build_main_agent_deepagent_middleware(
             task_description=TASK_TOOL_DESCRIPTION,
             workspace_id=workspace_id,
         ),
+        build_continue_on_max_length_mw(flags),
         resilience.model_call_limit,
         resilience.tool_call_limit,
         build_context_editing_mw(
diff --git a/surfsense_backend/app/agents/chat/multi_agent_chat/main_agent/middleware/tool_call_repair/builder.py b/surfsense_backend/app/agents/chat/multi_agent_chat/main_agent/middleware/tool_call_repair/builder.py
index a1cc558b2..09fd72e56 100644
--- a/surfsense_backend/app/agents/chat/multi_agent_chat/main_agent/middleware/tool_call_repair/builder.py
+++ b/surfsense_backend/app/agents/chat/multi_agent_chat/main_agent/middleware/tool_call_repair/builder.py
@@ -11,28 +11,7 @@ from app.agents.chat.multi_agent_chat.shared.middleware.flags import enabled
 
 from .middleware import ToolCallNameRepairMiddleware
 
-# deepagents-built-in tool names the repair pass treats as known.
-_DEEPAGENT_BUILTIN_TOOL_NAMES: frozenset[str] = frozenset(
-    {
-        "write_todos",
-        "ls",
-        "read_file",
-        "write_file",
-        "edit_file",
-        "glob",
-        "grep",
-        "execute",
-        "task",
-        "mkdir",
-        "cd",
-        "pwd",
-        "move_file",
-        "rm",
-        "rmdir",
-        "list_tree",
-        "execute_code",
-    }
-)
+_MIDDLEWARE_BOUND_TOOL_NAMES: frozenset[str] = frozenset({"task", "write_todos"})
 
 
 def build_repair_mw(
@@ -43,7 +22,7 @@ def build_repair_mw(
     if not enabled(flags, "enable_tool_call_repair"):
         return None
     registered_names: set[str] = {t.name for t in tools}
-    registered_names |= _DEEPAGENT_BUILTIN_TOOL_NAMES
+    registered_names |= _MIDDLEWARE_BOUND_TOOL_NAMES
     return ToolCallNameRepairMiddleware(
         registered_tool_names=registered_names,
         fuzzy_match_threshold=None,
diff --git a/surfsense_backend/app/agents/chat/multi_agent_chat/shared/feature_flags.py b/surfsense_backend/app/agents/chat/multi_agent_chat/shared/feature_flags.py
index 91ee2a4c6..f362fe38e 100644
--- a/surfsense_backend/app/agents/chat/multi_agent_chat/shared/feature_flags.py
+++ b/surfsense_backend/app/agents/chat/multi_agent_chat/shared/feature_flags.py
@@ -44,6 +44,8 @@ class AgentFeatureFlags:
     enable_tool_call_limit: bool = True
     enable_tool_call_repair: bool = True
     enable_doom_loop: bool = True
+    # Stitch continuations onto a final answer cut off by max_tokens.
+    enable_continue_on_max_length: bool = True
 
     # Safety — permissions, concurrency, tool-set narrowing
     enable_permission: bool = True
@@ -105,6 +107,7 @@ class AgentFeatureFlags:
                 enable_tool_call_limit=False,
                 enable_tool_call_repair=False,
                 enable_doom_loop=False,
+                enable_continue_on_max_length=False,
                 enable_permission=False,
                 enable_busy_mutex=False,
                 enable_llm_tool_selector=False,
@@ -134,6 +137,9 @@ class AgentFeatureFlags:
                 "SURFSENSE_ENABLE_TOOL_CALL_REPAIR", True
             ),
             enable_doom_loop=_env_bool("SURFSENSE_ENABLE_DOOM_LOOP", True),
+            enable_continue_on_max_length=_env_bool(
+                "SURFSENSE_ENABLE_CONTINUE_ON_MAX_LENGTH", True
+            ),
             # Safety
             enable_permission=_env_bool("SURFSENSE_ENABLE_PERMISSION", True),
             enable_busy_mutex=_env_bool("SURFSENSE_ENABLE_BUSY_MUTEX", True),
@@ -176,6 +182,7 @@ class AgentFeatureFlags:
                 self.enable_tool_call_limit,
                 self.enable_tool_call_repair,
                 self.enable_doom_loop,
+                self.enable_continue_on_max_length,
                 self.enable_permission,
                 self.enable_busy_mutex,
                 self.enable_llm_tool_selector,
diff --git a/surfsense_backend/app/agents/chat/multi_agent_chat/shared/permissions/deny.py b/surfsense_backend/app/agents/chat/multi_agent_chat/shared/permissions/deny.py
index 83677b4ca..1ece81f70 100644
--- a/surfsense_backend/app/agents/chat/multi_agent_chat/shared/permissions/deny.py
+++ b/surfsense_backend/app/agents/chat/multi_agent_chat/shared/permissions/deny.py
@@ -36,4 +36,46 @@ def build_deny_message(tool_call: dict[str, Any], rule: Rule) -> ToolMessage:
     )
 
 
-__all__ = ["build_deny_message"]
+def build_reject_message(tool_call: dict[str, Any]) -> ToolMessage:
+    """Reject without feedback: model must stop retrying this call and ask the user."""
+    err = StreamingError(
+        code="permission_denied",
+        retryable=False,
+        suggestion="Do not retry this call; ask the user how to proceed.",
+    )
+    return ToolMessage(
+        content=(
+            f"The user rejected tool {tool_call.get('name')!r}. Do not retry the "
+            "same call; ask the user how they would like to proceed."
+        ),
+        tool_call_id=tool_call.get("id") or "",
+        name=tool_call.get("name"),
+        status="error",
+        additional_kwargs={"error": err.model_dump()},
+    )
+
+
+def build_correction_message(tool_call: dict[str, Any], feedback: str) -> ToolMessage:
+    """Reject with feedback: surface the correction so the model can retry differently."""
+    err = StreamingError(
+        code="permission_denied",
+        retryable=True,
+        suggestion="Adjust the call per the user's feedback and try again.",
+    )
+    return ToolMessage(
+        content=(
+            f"The user rejected tool {tool_call.get('name')!r} with feedback: "
+            f"{feedback}"
+        ),
+        tool_call_id=tool_call.get("id") or "",
+        name=tool_call.get("name"),
+        status="error",
+        additional_kwargs={"error": err.model_dump()},
+    )
+
+
+__all__ = [
+    "build_correction_message",
+    "build_deny_message",
+    "build_reject_message",
+]
diff --git a/surfsense_backend/app/agents/chat/multi_agent_chat/shared/permissions/middleware/core.py b/surfsense_backend/app/agents/chat/multi_agent_chat/shared/permissions/middleware/core.py
index a97e32379..d40943530 100644
--- a/surfsense_backend/app/agents/chat/multi_agent_chat/shared/permissions/middleware/core.py
+++ b/surfsense_backend/app/agents/chat/multi_agent_chat/shared/permissions/middleware/core.py
@@ -27,12 +27,11 @@ from langchain_core.tools import BaseTool
 from langgraph.runtime import Runtime
 
 from app.agents.chat.multi_agent_chat.shared.permissions.model import Ruleset
-from app.agents.chat.runtime.errors import CorrectedError, RejectedError
 from app.services.user_tool_allowlist import TrustedToolSaver
 
 from ..ask.edit import merge_edited_args
 from ..ask.request import request_permission_decision
-from ..deny import build_deny_message
+from ..deny import build_correction_message, build_deny_message, build_reject_message
 from .evaluation import evaluate_tool_call
 from .pattern_resolver import PatternResolver
 from .ruleset_view import all_rulesets
@@ -173,15 +172,16 @@ class PermissionMiddleware(AgentMiddleware):  # type: ignore[type-arg]
                 elif kind == "reject":
                     feedback = decision.get("feedback")
                     if isinstance(feedback, str) and feedback.strip():
-                        raise CorrectedError(feedback, tool=name)
-                    raise RejectedError(
-                        tool=name, pattern=patterns[0] if patterns else None
-                    )
+                        deny_messages.append(build_correction_message(call, feedback))
+                    else:
+                        deny_messages.append(build_reject_message(call))
+                    any_change = True
                 else:
                     logger.warning(
                         "Unknown permission decision %r; treating as reject", kind
                     )
-                    raise RejectedError(tool=name)
+                    deny_messages.append(build_reject_message(call))
+                    any_change = True
                 continue
 
             kept_calls.append(call)
diff --git a/surfsense_backend/app/agents/chat/multi_agent_chat/subagents/builtins/knowledge_base/ask_knowledge_base_tool.py b/surfsense_backend/app/agents/chat/multi_agent_chat/subagents/builtins/knowledge_base/ask_knowledge_base_tool.py
index 8b728674f..d2327471e 100644
--- a/surfsense_backend/app/agents/chat/multi_agent_chat/subagents/builtins/knowledge_base/ask_knowledge_base_tool.py
+++ b/surfsense_backend/app/agents/chat/multi_agent_chat/subagents/builtins/knowledge_base/ask_knowledge_base_tool.py
@@ -20,6 +20,11 @@ from .prompts import load_readonly_description
 
 TOOL_NAME = "ask_knowledge_base"
 
+_MISSING_TOOL_CALL_ID_ERROR = (
+    "Error: ask_knowledge_base was invoked without a tool call id and cannot "
+    "run. Retry the call as a normal tool call."
+)
+
 
 def _forward_state(runtime: ToolRuntime, query: str) -> dict:
     forwarded = {k: v for k, v in runtime.state.items() if k not in EXCLUDED_STATE_KEYS}
@@ -84,7 +89,7 @@ def build_ask_knowledge_base_tool(
         runtime: ToolRuntime,
     ) -> str | Command:
         if not runtime.tool_call_id:
-            raise ValueError("Tool call ID is required for ask_knowledge_base")
+            return _MISSING_TOOL_CALL_ID_ERROR
         sub_state = _forward_state(runtime, query)
         sub_config = subagent_invoke_config(runtime)
         result = _resolve().invoke(sub_state, config=sub_config)
@@ -99,7 +104,7 @@ def build_ask_knowledge_base_tool(
         runtime: ToolRuntime,
     ) -> str | Command:
         if not runtime.tool_call_id:
-            raise ValueError("Tool call ID is required for ask_knowledge_base")
+            return _MISSING_TOOL_CALL_ID_ERROR
         sub_state = _forward_state(runtime, query)
         sub_config = subagent_invoke_config(runtime)
         result = await _resolve().ainvoke(sub_state, config=sub_config)
diff --git a/surfsense_backend/app/agents/chat/runtime/errors.py b/surfsense_backend/app/agents/chat/runtime/errors.py
index a17333acc..7d7664f66 100644
--- a/surfsense_backend/app/agents/chat/runtime/errors.py
+++ b/surfsense_backend/app/agents/chat/runtime/errors.py
@@ -51,33 +51,6 @@ class StreamingError(BaseModel):
         frozen = True
 
 
-class RejectedError(Exception):
-    """Raised when the user rejects a permission ask without feedback.
-
-    Caught by :class:`PermissionMiddleware`; the agent stops the current
-    tool fan-out and surfaces a user-facing rejection.
-    """
-
-    def __init__(self, *, tool: str | None = None, pattern: str | None = None) -> None:
-        super().__init__(f"Permission rejected for tool {tool!r}, pattern {pattern!r}")
-        self.tool = tool
-        self.pattern = pattern
-
-
-class CorrectedError(Exception):
-    """Raised when the user rejects a permission ask *with* feedback.
-
-    The :class:`PermissionMiddleware` translates the feedback into a
-    synthetic ``ToolMessage`` so the model sees the user's correction
-    and can retry the request differently.
-    """
-
-    def __init__(self, feedback: str, *, tool: str | None = None) -> None:
-        super().__init__(feedback)
-        self.feedback = feedback
-        self.tool = tool
-
-
 class BusyError(Exception):
     """Raised when a second prompt arrives while the same thread is mid-stream."""
 
@@ -88,8 +61,6 @@ class BusyError(Exception):
 
 __all__ = [
     "BusyError",
-    "CorrectedError",
     "ErrorCode",
-    "RejectedError",
     "StreamingError",
 ]
diff --git a/surfsense_backend/app/routes/new_chat_routes.py b/surfsense_backend/app/routes/new_chat_routes.py
index 18fa15c28..48ddfc73f 100644
--- a/surfsense_backend/app/routes/new_chat_routes.py
+++ b/surfsense_backend/app/routes/new_chat_routes.py
@@ -63,6 +63,7 @@ from app.schemas.new_chat import (
     NewChatThreadUpdate,
     NewChatThreadVisibilityUpdate,
     NewChatThreadWithMessages,
+    PendingInterruptsResponse,
     PublicChatSnapshotCreateResponse,
     PublicChatSnapshotListResponse,
     RegenerateRequest,
@@ -223,6 +224,34 @@ def _raise_if_thread_busy_for_start(thread_id: int) -> None:
     )
 
 
+async def _raise_if_thread_awaiting_approval(thread_id: int, checkpointer) -> None:
+    """Refuse a fresh turn when the thread's checkpoint has a pending interrupt.
+
+    The busy mutex releases on an ``interrupt()`` pause, so a paused thread
+    reads as idle to ``_raise_if_thread_busy_for_start``. Running ``new_chat`` /
+    ``regenerate`` over that checkpoint would orphan the pending approval — the
+    user must resume or cancel it first. ``resume`` is exempt; it's the path
+    that clears the pause.
+    """
+    from app.tasks.chat.streaming.helpers.interrupt_inspector import (
+        pending_interrupt_entries_from_writes,
+    )
+
+    checkpoint_tuple = await checkpointer.aget_tuple(
+        {"configurable": {"thread_id": str(thread_id)}}
+    )
+    if checkpoint_tuple is None:
+        return
+    if pending_interrupt_entries_from_writes(checkpoint_tuple.pending_writes):
+        raise HTTPException(
+            status_code=409,
+            detail={
+                "errorCode": "THREAD_AWAITING_APPROVAL",
+                "message": chat_error_message("THREAD_AWAITING_APPROVAL"),
+            },
+        )
+
+
 def _find_pre_turn_checkpoint_id(
     checkpoint_tuples: list,
     *,
@@ -1743,6 +1772,11 @@ async def handle_new_chat(
         # Check thread-level access based on visibility
         await check_thread_access(session, thread, user)
         _raise_if_thread_busy_for_start(request.chat_id)
+        from app.agents.chat.runtime.checkpointer import get_checkpointer
+
+        await _raise_if_thread_awaiting_approval(
+            request.chat_id, await get_checkpointer()
+        )
         filesystem_selection = _resolve_filesystem_selection(
             mode=request.filesystem_mode,
             client_platform=request.client_platform,
@@ -1980,15 +2014,16 @@ async def regenerate_response(
         # Check thread-level access based on visibility
         await check_thread_access(session, thread, user)
         _raise_if_thread_busy_for_start(thread_id)
+
+        # Get the checkpointer and state history
+        checkpointer = await get_checkpointer()
+        await _raise_if_thread_awaiting_approval(thread_id, checkpointer)
         filesystem_selection = _resolve_filesystem_selection(
             mode=request.filesystem_mode,
             client_platform=request.client_platform,
             local_mounts=request.local_filesystem_mounts,
         )
 
-        # Get the checkpointer and state history
-        checkpointer = await get_checkpointer()
-
         config = {"configurable": {"thread_id": str(thread_id)}}
 
         # Collect checkpoint tuples from the async iterator
@@ -2376,6 +2411,86 @@ async def regenerate_response(
 # =============================================================================
 
 
+@router.get(
+    "/threads/{thread_id}/pending-interrupts",
+    response_model=PendingInterruptsResponse,
+)
+async def get_pending_interrupts(
+    thread_id: int,
+    session: AsyncSession = Depends(get_async_session),
+    auth: AuthContext = Depends(get_auth_context),
+):
+    """Return the thread's paused HITL interrupts, if any.
+
+    The live approval card lives only in the frontend's in-memory stream
+    overlay, so a page refresh loses it while the LangGraph checkpoint stays
+    paused. The frontend calls this on thread load to re-render the card and
+    let the user resume or reject.
+    """
+    from app.agents.chat.runtime.checkpointer import get_checkpointer
+    from app.services.new_streaming_service import VercelStreamingService
+    from app.tasks.chat.streaming.helpers.interrupt_inspector import (
+        pending_interrupt_entries_from_writes,
+    )
+
+    result = await session.execute(
+        select(NewChatThread).filter(NewChatThread.id == thread_id)
+    )
+    thread = result.scalars().first()
+    if not thread:
+        raise HTTPException(status_code=404, detail="Thread not found")
+
+    await check_permission(
+        session,
+        auth,
+        thread.workspace_id,
+        Permission.CHATS_READ.value,
+        "You don't have permission to read chats in this workspace",
+    )
+    await check_thread_access(session, thread, user=auth.user)
+
+    checkpointer = await get_checkpointer()
+    checkpoint_tuple = await checkpointer.aget_tuple(
+        {"configurable": {"thread_id": str(thread_id)}}
+    )
+    if checkpoint_tuple is None:
+        return PendingInterruptsResponse()
+
+    entries = pending_interrupt_entries_from_writes(checkpoint_tuple.pending_writes)
+    if not entries:
+        return PendingInterruptsResponse()
+
+    service = VercelStreamingService()
+    payloads: list[dict] = []
+    for value, interrupt_id in entries:
+        payload = service._normalize_interrupt_payload(value)
+        if interrupt_id is not None:
+            payload = {**payload, "interrupt_id": interrupt_id}
+        payloads.append(payload)
+
+    # Reattach the card to the paused turn's assistant row. ``turn_id`` on the
+    # checkpoint mirrors ``NewChatMessage.turn_id``; fall back to the newest
+    # assistant row (the paused turn is always the head).
+    metadata = checkpoint_tuple.metadata or {}
+    turn_id = metadata.get("turn_id") if isinstance(metadata, dict) else None
+    assistant_query = (
+        select(NewChatMessage.id)
+        .filter(
+            NewChatMessage.thread_id == thread_id,
+            NewChatMessage.role == NewChatMessageRole.ASSISTANT,
+        )
+        .order_by(NewChatMessage.created_at.desc())
+    )
+    if turn_id:
+        assistant_query = assistant_query.filter(NewChatMessage.turn_id == turn_id)
+    assistant_message_id = (await session.execute(assistant_query.limit(1))).scalar()
+
+    return PendingInterruptsResponse(
+        assistant_message_id=assistant_message_id,
+        pending_interrupts=payloads,
+    )
+
+
 @router.post("/threads/{thread_id}/resume")
 async def resume_chat(
     thread_id: int,
diff --git a/surfsense_backend/app/schemas/new_chat.py b/surfsense_backend/app/schemas/new_chat.py
index d0fc8822d..443cda7d4 100644
--- a/surfsense_backend/app/schemas/new_chat.py
+++ b/surfsense_backend/app/schemas/new_chat.py
@@ -425,6 +425,7 @@ class AgentToolInfo(BaseModel):
 class ResumeDecision(BaseModel):
     type: Literal["approve", "edit", "reject", "approve_always"]
     edited_action: dict[str, Any] | None = None
+    tool_call_id: str | None = None
 
 
 class ResumeRequest(BaseModel):
@@ -458,6 +459,20 @@ class ResumeRequest(BaseModel):
     )
 
 
+class PendingInterruptsResponse(BaseModel):
+    """Paused HITL interrupts for a thread, reconstructed from the checkpoint.
+
+    Lets the frontend re-render approval cards after a page refresh (the live
+    ``chatStreamStore`` overlay lives only in module RAM). Each payload matches
+    the ``data-interrupt-request`` SSE ``data`` shape (carries ``interrupt_id``
+    / ``tool_call_id``); ``assistant_message_id`` is the paused turn's row so
+    the card reattaches to the right message.
+    """
+
+    assistant_message_id: int | None = None
+    pending_interrupts: list[dict[str, Any]] = Field(default_factory=list)
+
+
 class CancelActiveTurnResponse(BaseModel):
     """Response for canceling an active turn on a chat thread."""
 
diff --git a/surfsense_backend/app/services/new_streaming_service.py b/surfsense_backend/app/services/new_streaming_service.py
index 87d9cf70f..303cf9c0b 100644
--- a/surfsense_backend/app/services/new_streaming_service.py
+++ b/surfsense_backend/app/services/new_streaming_service.py
@@ -506,18 +506,25 @@ class VercelStreamingService:
             },
         )
 
-    def format_interrupt_request(self, interrupt_value: dict[str, Any]) -> str:
+    def format_interrupt_request(
+        self, interrupt_value: dict[str, Any], *, interrupt_id: str | None = None
+    ) -> str:
         """Format an interrupt request for human-in-the-loop approval.
 
         Args:
             interrupt_value: The interrupt payload from either:
                 - interrupt_on config: {action_requests: [...], review_configs: [...]}
                 - interrupt() primitive: {type: "...", message: "...", action: {...}, context: {...}}
+            interrupt_id: langgraph ``Interrupt.id``. The only stable handle for
+                parent-side interrupts (doom-loop, permission asks) that carry no
+                ``tool_call_id``; the frontend uses it to render and resume them.
 
         Returns:
             str: SSE formatted interrupt request data part
         """
         normalized_payload = self._normalize_interrupt_payload(interrupt_value)
+        if interrupt_id is not None:
+            normalized_payload = {**normalized_payload, "interrupt_id": interrupt_id}
         return self.format_data("interrupt-request", normalized_payload)
 
     def _normalize_interrupt_payload(
diff --git a/surfsense_backend/app/services/token_tracking_service.py b/surfsense_backend/app/services/token_tracking_service.py
index 2b4ec4273..32ee03ba7 100644
--- a/surfsense_backend/app/services/token_tracking_service.py
+++ b/surfsense_backend/app/services/token_tracking_service.py
@@ -32,6 +32,25 @@ from app.db import TokenUsage
 logger = logging.getLogger(__name__)
 
 
+def is_output_truncated(
+    finish_reason: str | None,
+    completion_tokens: int,
+    max_tokens: int | None,
+) -> bool:
+    """True when a generation was cut off by the model's output-token cap.
+
+    ``finish_reason == "length"`` is authoritative. When it is absent —
+    ``langchain_litellm`` drops it from streamed chunks — fall back to usage:
+    hitting the configured ``max_tokens`` is the same event in practice. Any
+    other explicit reason (``stop``/``tool_calls``/…) is a clean finish.
+    """
+    if finish_reason == "length":
+        return True
+    if finish_reason:
+        return False
+    return bool(max_tokens) and completion_tokens >= max_tokens
+
+
 def _bare_model_name(model: str) -> str:
     """Return a model identifier with any provider routing prefix stripped.
 
@@ -75,6 +94,8 @@ class TurnTokenAccumulator:
     model_metadata_by_bare: dict[str, dict[str, str | None]] = field(
         default_factory=dict
     )
+    # Set when any chat call in the turn was cut off by its output-token cap.
+    truncated: bool = False
 
     def register_model_metadata(
         self,
@@ -468,6 +489,17 @@ class TokenTrackingCallback(CustomLogger):
             call_kind=call_kind,
         )
 
+        # Streaming drops finish_reason, but the reconstructed response_obj keeps it.
+        if not is_image:
+            choices = getattr(response_obj, "choices", None) or []
+            finish_reason = (
+                getattr(choices[0], "finish_reason", None) if choices else None
+            )
+            if is_output_truncated(
+                finish_reason, completion_tokens, kwargs.get("max_tokens")
+            ):
+                acc.truncated = True
+
         # Per-LLM-call wall-clock latency (LiteLLM passes datetime objects).
         call_latency_s: float | None = None
         try:
diff --git a/surfsense_backend/app/tasks/chat/streaming/agent/event_loop.py b/surfsense_backend/app/tasks/chat/streaming/agent/event_loop.py
index 511b89b06..d94a85941 100644
--- a/surfsense_backend/app/tasks/chat/streaming/agent/event_loop.py
+++ b/surfsense_backend/app/tasks/chat/streaming/agent/event_loop.py
@@ -30,7 +30,7 @@ from app.tasks.chat.streaming.contract.file_contract import (
 )
 from app.tasks.chat.streaming.graph_stream.event_stream import stream_output
 from app.tasks.chat.streaming.helpers.interrupt_inspector import (
-    all_interrupt_values,
+    all_interrupt_entries,
 )
 from app.tasks.chat.streaming.shared.stream_result import StreamResult
 from app.tasks.chat.streaming.shared.utils import safe_float
@@ -125,7 +125,8 @@ async def stream_agent_events(
 
     # A turn paused for approval is not a finished turn: the graph resumes into
     # this same working copy, so the copy has to outlive the stream.
-    pending_values = all_interrupt_values(state)
+    pending_entries = all_interrupt_entries(state)
+    pending_values = [value for value, _ in pending_entries]
 
     # Same safety net for the git-native path. The pending state is the turn's
     # working copy on disk, so no state markers gate it: no copy (or aafter_agent
@@ -221,5 +222,7 @@ async def stream_agent_events(
         # the resume slicer in
         # ``checkpointed_subagent_middleware.resume_routing`` consumes in the
         # same order — keeping emit and resume in lock-step.
-        for interrupt_value in pending_values:
-            yield streaming_service.format_interrupt_request(interrupt_value)
+        for interrupt_value, interrupt_id in pending_entries:
+            yield streaming_service.format_interrupt_request(
+                interrupt_value, interrupt_id=interrupt_id
+            )
diff --git a/surfsense_backend/app/tasks/chat/streaming/errors/messages.py b/surfsense_backend/app/tasks/chat/streaming/errors/messages.py
index 5f72ad403..b2de00827 100644
--- a/surfsense_backend/app/tasks/chat/streaming/errors/messages.py
+++ b/surfsense_backend/app/tasks/chat/streaming/errors/messages.py
@@ -41,6 +41,10 @@ CHAT_ERROR_MESSAGES: dict[str, str] = {
         "seconds or switch models."
     ),
     "SERVER_ERROR": ("We couldn't complete this response right now. Please try again."),
+    "THREAD_AWAITING_APPROVAL": (
+        "This thread is waiting on your approval. Respond to the pending action, "
+        "or stop the response, before sending a new message."
+    ),
     "THREAD_BUSY": (
         "Another response is still finishing for this thread. Please try again "
         "in a moment."
diff --git a/surfsense_backend/app/tasks/chat/streaming/flows/resume_chat/resume_routing.py b/surfsense_backend/app/tasks/chat/streaming/flows/resume_chat/resume_routing.py
index d9877c9b0..8b8b2068c 100644
--- a/surfsense_backend/app/tasks/chat/streaming/flows/resume_chat/resume_routing.py
+++ b/surfsense_backend/app/tasks/chat/streaming/flows/resume_chat/resume_routing.py
@@ -43,18 +43,40 @@ async def build_resume_routing(
     """
     from app.agents.chat.multi_agent_chat.main_agent.middleware.checkpointed_subagent_middleware.resume_routing import (
         build_lg_resume_map,
+        build_parent_resume_map,
+        collect_pending_parent_interrupts,
         collect_pending_tool_calls,
         slice_decisions_by_tool_call,
     )
 
     parent_state = await agent.aget_state({"configurable": {"thread_id": str(chat_id)}})
     pending = collect_pending_tool_calls(parent_state)
+    parent_pending = collect_pending_parent_interrupts(parent_state)
     _perf_log.info(
-        "[hitl_route] resume_entry chat_id=%s decisions=%d pending_subagents=%d",
+        "[hitl_route] resume_entry chat_id=%s decisions=%d pending_subagents=%d "
+        "pending_parent=%d",
         chat_id,
         len(decisions),
         len(pending),
+        len(parent_pending),
     )
+
+    if parent_pending:
+        # Parent-side interrupts route by Interrupt.id with no subagent bridge.
+        # A mix with subagent pauses can't occur (they fire pre-delegation);
+        # fail loud rather than mis-route.
+        if pending:
+            raise ValueError(
+                "Cannot resume: both parent-side and subagent-side interrupts "
+                f"are pending (parent={len(parent_pending)}, "
+                f"subagent={len(pending)}); mixed HITL routing is unsupported."
+            )
+        lg_resume_map = build_parent_resume_map(decisions, parent_pending)
+        return ResumeRoutingPayload(
+            routed_resume_value={},
+            lg_resume_map=lg_resume_map,
+        )
+
     routed_resume_value = slice_decisions_by_tool_call(decisions, pending)
     lg_resume_map = build_lg_resume_map(parent_state, routed_resume_value)
     return ResumeRoutingPayload(
diff --git a/surfsense_backend/app/tasks/chat/streaming/flows/shared/finalize_emit.py b/surfsense_backend/app/tasks/chat/streaming/flows/shared/finalize_emit.py
index e5de3f6a4..495d4dbd4 100644
--- a/surfsense_backend/app/tasks/chat/streaming/flows/shared/finalize_emit.py
+++ b/surfsense_backend/app/tasks/chat/streaming/flows/shared/finalize_emit.py
@@ -50,5 +50,6 @@ def iter_token_usage_frame(
                 "total_tokens": accumulator.grand_total,
                 "cost_micros": accumulator.total_cost_micros,
                 "call_details": accumulator.serialized_calls(),
+                "truncated": accumulator.truncated,
             },
         )
diff --git a/surfsense_backend/app/tasks/chat/streaming/helpers/interrupt_inspector.py b/surfsense_backend/app/tasks/chat/streaming/helpers/interrupt_inspector.py
index f4b00431c..9858b620c 100644
--- a/surfsense_backend/app/tasks/chat/streaming/helpers/interrupt_inspector.py
+++ b/surfsense_backend/app/tasks/chat/streaming/helpers/interrupt_inspector.py
@@ -9,33 +9,45 @@ correlates each frame back to the right paused subagent via the stamped
 
 from __future__ import annotations
 
+from collections.abc import Iterable
 from typing import Any
 
+# LangGraph persists interrupts as writes to this channel, one per paused task.
+# The named constant is private as of V1.0, but the channel string is the
+# durable on-disk value.
+_INTERRUPT_CHANNEL = "__interrupt__"
 
-def all_interrupt_values(state: Any) -> list[dict[str, Any]]:
-    """Return every interrupt payload across the snapshot, in traversal order.
+
+def all_interrupt_entries(state: Any) -> list[tuple[dict[str, Any], str | None]]:
+    """Return ``(value, interrupt_id)`` for every pending interrupt, in order.
 
     Walks ``state.tasks[*].interrupts`` first (langgraph's per-task buckets,
     which carry one interrupt per paused subagent) and falls back to
     ``state.interrupts`` when the per-task lists are empty. Order matches the
     snapshot's iteration order so the emit-time order on the SSE stream agrees
-    with ``collect_pending_tool_calls`` consumption order on resume.
+    with the resume slicer's consumption order.
+
+    The ``interrupt_id`` (langgraph ``Interrupt.id``) is the only stable handle
+    for parent-side interrupts (doom-loop, permission asks) that carry no
+    ``tool_call_id``; it lets the frontend render and resume them.
 
     Defensive against malformed snapshots: tasks/interrupts that raise on
     attribute access are skipped silently. Non-dict values are skipped — the
     chat-stream contract requires structured interrupt payloads.
     """
 
-    def _extract(candidate: Any) -> dict[str, Any] | None:
+    def _extract(candidate: Any) -> tuple[dict[str, Any], str | None] | None:
         if isinstance(candidate, dict):
             value = candidate.get("value", candidate)
-            return value if isinstance(value, dict) else None
-        value = getattr(candidate, "value", None)
-        if isinstance(value, dict):
-            return value
-        return None
+            interrupt_id = candidate.get("id")
+        else:
+            value = getattr(candidate, "value", None)
+            interrupt_id = getattr(candidate, "id", None)
+        if not isinstance(value, dict):
+            return None
+        return value, (str(interrupt_id) if interrupt_id is not None else None)
 
-    values: list[dict[str, Any]] = []
+    entries: list[tuple[dict[str, Any], str | None]] = []
     saw_task_interrupt = False
 
     for task in getattr(state, "tasks", ()) or ():
@@ -48,10 +60,10 @@ def all_interrupt_values(state: Any) -> list[dict[str, Any]]:
             for interrupt_item in interrupts:
                 extracted = _extract(interrupt_item)
                 if extracted is not None:
-                    values.append(extracted)
+                    entries.append(extracted)
 
     if saw_task_interrupt:
-        return values
+        return entries
 
     try:
         state_interrupts = getattr(state, "interrupts", ()) or ()
@@ -60,5 +72,48 @@ def all_interrupt_values(state: Any) -> list[dict[str, Any]]:
     for interrupt_item in state_interrupts:
         extracted = _extract(interrupt_item)
         if extracted is not None:
-            values.append(extracted)
-    return values
+            entries.append(extracted)
+    return entries
+
+
+def all_interrupt_values(state: Any) -> list[dict[str, Any]]:
+    """Interrupt payloads across the snapshot, in traversal order (ids dropped)."""
+    return [value for value, _ in all_interrupt_entries(state)]
+
+
+def pending_interrupt_entries_from_writes(
+    pending_writes: Iterable[Any] | None,
+) -> list[tuple[dict[str, Any], str | None]]:
+    """``(value, interrupt_id)`` for interrupts stored in a checkpoint's writes.
+
+    Reads paused interrupts without compiling the agent graph, so the
+    thread-load path can surface HITL cards after a refresh — ``aget_state``
+    (which would compute these) needs the full compiled agent and is far too
+    heavy for a read. Each ``pending_writes`` entry is ``(task_id, channel,
+    value)``; interrupt writes carry one or more langgraph ``Interrupt``
+    objects on the ``"__interrupt__"`` channel.
+
+    ponytail: couples to the persisted channel string. If langgraph renames it,
+    switch to ``graph.aget_state(config).interrupts``.
+    """
+    entries: list[tuple[dict[str, Any], str | None]] = []
+    for write in pending_writes or ():
+        try:
+            _task_id, channel, value = write
+        except (ValueError, TypeError):
+            continue
+        if channel != _INTERRUPT_CHANNEL:
+            continue
+        items = value if isinstance(value, list | tuple) else [value]
+        for item in items:
+            interrupt_value = getattr(item, "value", None)
+            interrupt_id = getattr(item, "id", None)
+            if not isinstance(interrupt_value, dict):
+                continue
+            entries.append(
+                (
+                    interrupt_value,
+                    str(interrupt_id) if interrupt_id is not None else None,
+                )
+            )
+    return entries
diff --git a/surfsense_backend/app/tasks/document_processors/_save.py b/surfsense_backend/app/tasks/document_processors/_save.py
index 2509a70ef..fe78931e3 100644
--- a/surfsense_backend/app/tasks/document_processors/_save.py
+++ b/surfsense_backend/app/tasks/document_processors/_save.py
@@ -1,7 +1,5 @@
 """Unified document save/update logic for file processors."""
 
-import logging
-
 from sqlalchemy.exc import SQLAlchemyError
 from sqlalchemy.ext.asyncio import AsyncSession
 
@@ -125,13 +123,6 @@ async def save_file_document(
 
     except SQLAlchemyError as db_error:
         await session.rollback()
-        if "ix_documents_content_hash" in str(db_error):
-            logging.warning(
-                "content_hash collision during commit for %s (%s). Skipping.",
-                file_name,
-                etl_service,
-            )
-            return None
         raise db_error
     except Exception as e:
         await session.rollback()
diff --git a/surfsense_backend/tests/integration/knowledge_store/index/test_duplicate_content_convergence.py b/surfsense_backend/tests/integration/knowledge_store/index/test_duplicate_content_convergence.py
new file mode 100644
index 000000000..29c84b4f1
--- /dev/null
+++ b/surfsense_backend/tests/integration/knowledge_store/index/test_duplicate_content_convergence.py
@@ -0,0 +1,59 @@
+"""Two git paths, identical bytes must converge into two rows.
+"""
+
+from __future__ import annotations
+
+import pytest
+from sqlalchemy import select
+
+from app.config import config as app_config
+from app.db import Document
+from app.knowledge_store import KnowledgeStore
+from app.knowledge_store.identities import user_identity
+from app.knowledge_store.index.converge import index_changes
+from app.utils.document_converters import generate_content_hash
+
+pytestmark = pytest.mark.integration
+
+DUPLICATE = "# Shared\n\nidentical bytes at two paths\n"
+
+
+@pytest.fixture
+def knowledge_root(tmp_path, monkeypatch):
+    monkeypatch.setattr(app_config, "KNOWLEDGE_STORE_ENABLED", True)
+    monkeypatch.setattr(app_config, "KNOWLEDGE_STORE_ROOT", str(tmp_path))
+    return tmp_path
+
+
+@pytest.fixture
+def store(knowledge_root, db_workspace):
+    return KnowledgeStore.for_workspace(db_workspace.id)
+
+
+async def _commit_two_identical_files(store):
+    async with store.transaction(message="test", author=user_identity("1")) as tx:
+        tx.write("documents/a.xml", DUPLICATE.encode())
+        tx.write("documents/b.xml", DUPLICATE.encode())
+    return tx.revision
+
+
+async def test_identical_content_at_two_paths_converges_to_two_rows(
+    store, db_session, db_workspace, patched_embed_texts, patched_chunk_text
+):
+    await _commit_two_identical_files(store)
+
+    await index_changes(db_session, db_workspace.id)
+
+    rows = (
+        (
+            await db_session.execute(
+                select(Document).where(Document.workspace_id == db_workspace.id)
+            )
+        )
+        .scalars()
+        .all()
+    )
+    assert {row.path for row in rows} == {"/documents/a.xml", "/documents/b.xml"}
+    assert {row.content_hash for row in rows} == {
+        generate_content_hash(DUPLICATE, db_workspace.id)
+    }
diff --git a/surfsense_backend/tests/unit/agents/multi_agent_chat/middleware/checkpointed_subagent_middleware/test_resume_decision_routing.py b/surfsense_backend/tests/unit/agents/multi_agent_chat/middleware/checkpointed_subagent_middleware/test_resume_decision_routing.py
index 62f33addc..d53dd4235 100644
--- a/surfsense_backend/tests/unit/agents/multi_agent_chat/middleware/checkpointed_subagent_middleware/test_resume_decision_routing.py
+++ b/surfsense_backend/tests/unit/agents/multi_agent_chat/middleware/checkpointed_subagent_middleware/test_resume_decision_routing.py
@@ -72,6 +72,93 @@ class TestSliceDecisionsByToolCall:
         assert routed == {}
 
 
+class TestIdBasedRouting:
+    """Decisions carrying a ``tool_call_id`` route by identity, not position."""
+
+    def test_routes_by_id_ignoring_submission_order(self):
+        decisions = [
+            {"type": "reject", "tool_call_id": "tcid-B"},
+            {"type": "approve", "tool_call_id": "tcid-A"},
+        ]
+        pending = [("tcid-A", 1), ("tcid-B", 1)]
+
+        routed = slice_decisions_by_tool_call(decisions, pending)
+
+        assert routed == {
+            "tcid-A": {"decisions": [{"type": "approve", "tool_call_id": "tcid-A"}]},
+            "tcid-B": {"decisions": [{"type": "reject", "tool_call_id": "tcid-B"}]},
+        }
+
+    def test_groups_multi_action_bundle_by_id(self):
+        decisions = [
+            {"type": "approve", "tool_call_id": "tcid-B"},
+            {"type": "approve", "tool_call_id": "tcid-A"},
+            {"type": "edit", "tool_call_id": "tcid-A"},
+        ]
+        pending = [("tcid-A", 2), ("tcid-B", 1)]
+
+        routed = slice_decisions_by_tool_call(decisions, pending)
+
+        assert routed == {
+            "tcid-A": {
+                "decisions": [
+                    {"type": "approve", "tool_call_id": "tcid-A"},
+                    {"type": "edit", "tool_call_id": "tcid-A"},
+                ]
+            },
+            "tcid-B": {"decisions": [{"type": "approve", "tool_call_id": "tcid-B"}]},
+        }
+
+    def test_raises_on_unknown_id(self):
+        decisions = [{"type": "approve", "tool_call_id": "tcid-ghost"}]
+        pending = [("tcid-A", 1)]
+
+        with pytest.raises(ValueError, match="tcid-ghost|does not match"):
+            slice_decisions_by_tool_call(decisions, pending)
+
+    def test_raises_on_missing_id(self):
+        decisions = [{"type": "approve", "tool_call_id": "tcid-A"}]
+        pending = [("tcid-A", 1), ("tcid-B", 1)]
+
+        with pytest.raises(ValueError, match="tcid-B|does not match"):
+            slice_decisions_by_tool_call(decisions, pending)
+
+    def test_raises_on_per_id_count_mismatch(self):
+        decisions = [
+            {"type": "approve", "tool_call_id": "tcid-A"},
+            {"type": "approve", "tool_call_id": "tcid-A"},
+        ]
+        pending = [("tcid-A", 1)]
+
+        with pytest.raises(ValueError, match="tcid-A|count"):
+            slice_decisions_by_tool_call(decisions, pending)
+
+    def test_partial_ids_fall_back_to_positional(self):
+        decisions = [
+            {"type": "approve"},
+            {"type": "reject", "tool_call_id": "tcid-B"},
+        ]
+        pending = [("tcid-A", 1), ("tcid-B", 1)]
+
+        routed = slice_decisions_by_tool_call(decisions, pending)
+
+        assert routed == {
+            "tcid-A": {"decisions": [decisions[0]]},
+            "tcid-B": {"decisions": [decisions[1]]},
+        }
+
+    def test_null_ids_fall_back_to_positional(self):
+        decisions = [
+            {"type": "approve", "tool_call_id": None},
+            {"type": "reject", "tool_call_id": None},
+        ]
+        pending = [("tcid-only", 2)]
+
+        routed = slice_decisions_by_tool_call(decisions, pending)
+
+        assert routed == {"tcid-only": {"decisions": decisions}}
+
+
 def _interrupt_with(tool_call_id: str, action_count: int):
     return SimpleNamespace(
         id=f"i-{tool_call_id}",
diff --git a/surfsense_backend/tests/unit/agents/multi_agent_chat/middleware/checkpointed_subagent_middleware/test_task_tool_missing_runtime.py b/surfsense_backend/tests/unit/agents/multi_agent_chat/middleware/checkpointed_subagent_middleware/test_task_tool_missing_runtime.py
new file mode 100644
index 000000000..8ef045933
--- /dev/null
+++ b/surfsense_backend/tests/unit/agents/multi_agent_chat/middleware/checkpointed_subagent_middleware/test_task_tool_missing_runtime.py
@@ -0,0 +1,42 @@
+"""``task`` returns a model-readable error when no tool runtime is injected.
+
+A truncated/mangled tool call can reach the ``task`` closure without LangChain
+injecting ``ToolRuntime`` (``runtime is None``). Both the sync and async paths
+must degrade to a ToolMessage-able string instead of raising ``AttributeError``
+on ``runtime.tool_call_id`` and killing the turn.
+"""
+
+from __future__ import annotations
+
+import pytest
+from langchain_core.runnables import RunnableLambda
+
+from app.agents.chat.multi_agent_chat.main_agent.middleware.checkpointed_subagent_middleware.task_tool import (
+    build_task_tool_with_parent_config,
+)
+
+pytestmark = pytest.mark.unit
+
+
+def _tool():
+    sub = RunnableLambda(lambda s: {"messages": []})
+    # workspace_id=None so the async path's spawn-paused check bypasses Redis.
+    return build_task_tool_with_parent_config(
+        [{"name": "alpha", "description": "alpha", "runnable": sub}],
+        workspace_id=None,
+    )
+
+
+def test_sync_missing_runtime_returns_error_string() -> None:
+    out = _tool().func(description="x", subagent_type="alpha", runtime=None)
+
+    assert isinstance(out, str)
+    assert "runtime" in out.lower()
+
+
+@pytest.mark.asyncio
+async def test_async_missing_runtime_returns_error_string() -> None:
+    out = await _tool().coroutine(description="x", subagent_type="alpha", runtime=None)
+
+    assert isinstance(out, str)
+    assert "runtime" in out.lower()
diff --git a/surfsense_backend/tests/unit/agents/multi_agent_chat/middleware/checkpointed_subagent_middleware/test_task_tool_runtime_injection.py b/surfsense_backend/tests/unit/agents/multi_agent_chat/middleware/checkpointed_subagent_middleware/test_task_tool_runtime_injection.py
new file mode 100644
index 000000000..f1c0f3bbe
--- /dev/null
+++ b/surfsense_backend/tests/unit/agents/multi_agent_chat/middleware/checkpointed_subagent_middleware/test_task_tool_runtime_injection.py
@@ -0,0 +1,72 @@
+"""``ToolRuntime`` must be injected into ``task`` through the real ToolNode.
+
+Regression guard for the custom ``args_schema``: if the schema omits the
+directly-injected ``runtime`` field, pydantic validation silently drops the
+ToolNode-injected runtime and every ``task`` call fails with ``runtime=None``.
+This drives the tool exactly as the agent does (StateGraph + ToolNode) and
+asserts the subagent actually runs.
+"""
+
+from __future__ import annotations
+
+from typing import Annotated
+
+import pytest
+from langchain_core.messages import AIMessage
+from langchain_core.runnables import RunnableLambda
+from langchain_core.utils.function_calling import convert_to_openai_tool
+from langgraph.graph import END, START, StateGraph
+from langgraph.graph.message import add_messages
+from langgraph.prebuilt import ToolNode
+from typing_extensions import TypedDict
+
+from app.agents.chat.multi_agent_chat.main_agent.middleware.checkpointed_subagent_middleware.task_tool import (
+    build_task_tool_with_parent_config,
+)
+
+pytestmark = pytest.mark.unit
+
+
+class _S(TypedDict):
+    messages: Annotated[list, add_messages]
+
+
+def _tool():
+    sub = RunnableLambda(lambda s: {"messages": [AIMessage(content="KB ran.")]})
+    return build_task_tool_with_parent_config(
+        [{"name": "knowledge_base", "description": "kb", "runnable": sub}],
+        workspace_id=1,
+    )
+
+
+@pytest.mark.asyncio
+async def test_runtime_is_injected_and_subagent_runs() -> None:
+    tool = _tool()
+    g = StateGraph(_S)
+    g.add_node("tools", ToolNode([tool]))
+    g.add_edge(START, "tools")
+    g.add_edge("tools", END)
+    app = g.compile()
+
+    ai = AIMessage(
+        content="",
+        tool_calls=[
+            {
+                "name": "task",
+                "args": {"description": "x", "subagent_type": "knowledge_base"},
+                "id": "call_1",
+                "type": "tool_call",
+            }
+        ],
+    )
+    out = await app.ainvoke({"messages": [ai]})
+
+    # If runtime were dropped, the tool returns the "could not read the tool
+    # runtime" guard string instead of the subagent's output.
+    assert "KB ran." in str(out["messages"][-1].content)
+
+
+def test_runtime_stays_out_of_model_facing_schema() -> None:
+    props = convert_to_openai_tool(_tool())["function"]["parameters"]["properties"]
+
+    assert "runtime" not in props
diff --git a/surfsense_backend/tests/unit/agents/multi_agent_chat/middleware/checkpointed_subagent_middleware/test_task_tool_subagent_type_enum.py b/surfsense_backend/tests/unit/agents/multi_agent_chat/middleware/checkpointed_subagent_middleware/test_task_tool_subagent_type_enum.py
new file mode 100644
index 000000000..757d3174b
--- /dev/null
+++ b/surfsense_backend/tests/unit/agents/multi_agent_chat/middleware/checkpointed_subagent_middleware/test_task_tool_subagent_type_enum.py
@@ -0,0 +1,66 @@
+"""``task.subagent_type`` is schema-constrained to the live roster.
+
+Guards three properties: the provider-facing schema advertises the roster as an
+enum, paused legacy-alias checkpoints still resolve (accepted-but-hidden), and an
+off-roster name comes back as a model-readable error instead of crashing.
+"""
+
+from __future__ import annotations
+
+import pytest
+from langchain_core.runnables import RunnableLambda
+from langchain_core.utils.function_calling import convert_to_openai_tool
+
+from app.agents.chat.multi_agent_chat.main_agent.middleware.checkpointed_subagent_middleware.task_tool import (
+    build_task_tool_with_parent_config,
+)
+
+pytestmark = pytest.mark.unit
+
+
+def _tool(names: list[str]):
+    sub = RunnableLambda(lambda s: {"messages": []})
+    return build_task_tool_with_parent_config(
+        [{"name": n, "description": n, "runnable": sub} for n in names]
+    )
+
+
+def _subagent_type_enum(tool) -> list[str] | None:
+    prop = convert_to_openai_tool(tool)["function"]["parameters"]["properties"][
+        "subagent_type"
+    ]
+    if "enum" in prop:
+        return prop["enum"]
+    for branch in prop.get("anyOf", []):
+        if "enum" in branch:
+            return branch["enum"]
+    return None
+
+
+def test_subagent_type_advertises_roster_enum() -> None:
+    tool = _tool(["knowledge_base", "web_crawler"])
+
+    assert _subagent_type_enum(tool) == ["knowledge_base", "web_crawler"]
+
+
+def test_legacy_alias_resolves_to_roster_and_stays_hidden() -> None:
+    tool = _tool(["mcp_discovery"])
+
+    assert tool.args_schema(subagent_type="gmail").subagent_type == "mcp_discovery"
+    assert "gmail" not in (_subagent_type_enum(tool) or [])
+
+
+def test_off_roster_name_returns_model_readable_error() -> None:
+    tool = _tool(["knowledge_base"])
+
+    out = tool.invoke(
+        {
+            "name": "task",
+            "args": {"description": "x", "subagent_type": "does_not_exist"},
+            "id": "call_1",
+            "type": "tool_call",
+        }
+    )
+
+    assert out.status == "error"
+    assert "knowledge_base" in out.content
diff --git a/surfsense_backend/tests/unit/agents/multi_agent_chat/middleware/shared/permissions/test_reject_emits_toolmessage.py b/surfsense_backend/tests/unit/agents/multi_agent_chat/middleware/shared/permissions/test_reject_emits_toolmessage.py
new file mode 100644
index 000000000..5237951d8
--- /dev/null
+++ b/surfsense_backend/tests/unit/agents/multi_agent_chat/middleware/shared/permissions/test_reject_emits_toolmessage.py
@@ -0,0 +1,67 @@
+"""Reject must degrade to a ToolMessage the model can continue from, not raise.
+
+``PermissionMiddleware`` used to ``raise RejectedError``/``CorrectedError`` on a
+reject decision. Nothing caught them, so a user rejection surfaced as a 500
+(``SERVER_ERROR``) and, for subagent-gated tools, killed the parent turn. Reject
+must instead emit a denial ToolMessage (mirroring the deny path) so the AI/Tool
+pairing stays valid and the model can adapt.
+"""
+
+from __future__ import annotations
+
+import pytest
+from langchain_core.messages import AIMessage, ToolMessage
+
+from app.agents.chat.multi_agent_chat.shared.permissions.middleware import core
+from app.agents.chat.multi_agent_chat.shared.permissions.middleware.core import (
+    PermissionMiddleware,
+)
+from app.agents.chat.multi_agent_chat.shared.permissions.model import Rule, Ruleset
+
+pytestmark = pytest.mark.unit
+
+
+def _mw(monkeypatch, decision: dict) -> PermissionMiddleware:
+    monkeypatch.setattr(core, "request_permission_decision", lambda **_kw: decision)
+    return PermissionMiddleware(
+        rulesets=[
+            Ruleset(
+                rules=[Rule(permission="edit_file", pattern="*", action="ask")],
+                origin="test",
+            )
+        ]
+    )
+
+
+def _state() -> dict:
+    ai = AIMessage(
+        content="",
+        tool_calls=[
+            {"name": "edit_file", "args": {"path": "/x"}, "id": "c1", "type": "tool_call"}
+        ],
+    )
+    return {"messages": [ai]}
+
+
+def test_reject_emits_toolmessage_and_drops_call(monkeypatch) -> None:
+    mw = _mw(monkeypatch, {"decision_type": "reject"})
+
+    update, _ = mw._process(_state(), None)
+
+    assert update is not None
+    tms = [m for m in update["messages"] if isinstance(m, ToolMessage)]
+    ai = next(m for m in update["messages"] if isinstance(m, AIMessage))
+    assert len(tms) == 1
+    assert tms[0].tool_call_id == "c1"
+    assert tms[0].status == "error"
+    assert ai.tool_calls == []
+
+
+def test_reject_with_feedback_carries_feedback(monkeypatch) -> None:
+    mw = _mw(monkeypatch, {"decision_type": "reject", "feedback": "use the trash bin"})
+
+    update, _ = mw._process(_state(), None)
+
+    tms = [m for m in update["messages"] if isinstance(m, ToolMessage)]
+    assert len(tms) == 1
+    assert "use the trash bin" in tms[0].content
diff --git a/surfsense_backend/tests/unit/agents/multi_agent_chat/middleware/test_continue_on_max_length.py b/surfsense_backend/tests/unit/agents/multi_agent_chat/middleware/test_continue_on_max_length.py
new file mode 100644
index 000000000..e3e1ac289
--- /dev/null
+++ b/surfsense_backend/tests/unit/agents/multi_agent_chat/middleware/test_continue_on_max_length.py
@@ -0,0 +1,173 @@
+"""Guard auto-continuation on output-token truncation.
+
+A tool-call-free text answer cut off by ``max_tokens`` should be re-invoked and
+stitched until it finishes; tool-call truncation and clean finishes pass through.
+"""
+
+from __future__ import annotations
+
+from dataclasses import dataclass, field, replace
+from typing import Any
+
+import pytest
+from langchain_core.messages import AIMessage, BaseMessage, HumanMessage
+
+from app.agents.chat.multi_agent_chat.main_agent.middleware.continue_on_max_length import (
+    ContinueOnMaxLengthMiddleware,
+)
+
+
+@dataclass
+class _FakeModel:
+    max_tokens: int | None = 24
+
+
+@dataclass
+class _FakeRequest:
+    model: _FakeModel
+    messages: list[BaseMessage] = field(default_factory=list)
+
+    def override(self, **overrides: Any) -> "_FakeRequest":
+        return replace(self, **overrides)
+
+
+@dataclass
+class _FakeResponse:
+    result: list[BaseMessage]
+    structured_response: Any = None
+
+
+def _ai(text: str, *, out: int, finish: str | None, tool_calls=None) -> AIMessage:
+    return AIMessage(
+        content=text,
+        tool_calls=tool_calls or [],
+        usage_metadata={"input_tokens": 5, "output_tokens": out, "total_tokens": 5 + out},
+        response_metadata={"finish_reason": finish} if finish else {},
+    )
+
+
+def _handler_from(queue: list[AIMessage]):
+    calls = {"n": 0}
+
+    async def handler(_request):
+        calls["n"] += 1
+        return _FakeResponse(result=[queue.pop(0)])
+
+    return handler, calls
+
+
+def _text(resp: _FakeResponse) -> str:
+    return resp.result[-1].content
+
+
+@pytest.mark.asyncio
+async def test_stitches_continuation_and_stops_when_complete():
+    mw = ContinueOnMaxLengthMiddleware(max_continuations=3)
+    handler, calls = _handler_from(
+        [
+            _ai("The ocean is ", out=24, finish="length"),
+            _ai("vast and deep.", out=6, finish="stop"),
+        ]
+    )
+    req = _FakeRequest(model=_FakeModel(max_tokens=24), messages=[HumanMessage("hi")])
+
+    resp = await mw.awrap_model_call(req, handler)
+
+    assert _text(resp) == "The ocean is vast and deep."
+    assert calls["n"] == 2
+
+
+@pytest.mark.asyncio
+async def test_clean_finish_passes_through_untouched():
+    mw = ContinueOnMaxLengthMiddleware(max_continuations=3)
+    handler, calls = _handler_from([_ai("All done.", out=5, finish="stop")])
+    req = _FakeRequest(model=_FakeModel(max_tokens=24), messages=[HumanMessage("hi")])
+
+    resp = await mw.awrap_model_call(req, handler)
+
+    assert _text(resp) == "All done."
+    assert calls["n"] == 1
+
+
+@pytest.mark.asyncio
+async def test_truncated_tool_call_is_not_continued():
+    mw = ContinueOnMaxLengthMiddleware(max_continuations=3)
+    truncated_tool = _ai(
+        "",
+        out=24,
+        finish="length",
+        tool_calls=[{"name": "search", "args": {"q": "x"}, "id": "t1"}],
+    )
+    handler, calls = _handler_from([truncated_tool])
+    req = _FakeRequest(model=_FakeModel(max_tokens=24), messages=[HumanMessage("hi")])
+
+    resp = await mw.awrap_model_call(req, handler)
+
+    assert resp.result[-1].tool_calls
+    assert calls["n"] == 1
+
+
+@pytest.mark.asyncio
+async def test_respects_continuation_cap_when_model_keeps_truncating():
+    mw = ContinueOnMaxLengthMiddleware(max_continuations=2)
+    handler, calls = _handler_from(
+        [_ai(c, out=24, finish="length") for c in "abcd"]
+    )
+    req = _FakeRequest(model=_FakeModel(max_tokens=24), messages=[HumanMessage("hi")])
+
+    resp = await mw.awrap_model_call(req, handler)
+
+    assert calls["n"] == 3  # 1 initial + 2 continuations, then give up
+    assert _text(resp) == "abc"
+
+
+@pytest.mark.asyncio
+async def test_successful_stitch_clears_truncation_marker():
+    from app.services import token_tracking_service as tt
+
+    acc = tt.start_turn()
+    acc.truncated = True
+    mw = ContinueOnMaxLengthMiddleware(max_continuations=3)
+    handler, _ = _handler_from(
+        [_ai("part ", out=24, finish="length"), _ai("whole.", out=6, finish="stop")]
+    )
+    req = _FakeRequest(model=_FakeModel(max_tokens=24), messages=[HumanMessage("hi")])
+
+    await mw.awrap_model_call(req, handler)
+
+    assert acc.truncated is False
+
+
+@pytest.mark.asyncio
+async def test_cap_exhaustion_keeps_truncation_marker():
+    from app.services import token_tracking_service as tt
+
+    acc = tt.start_turn()
+    acc.truncated = True
+    mw = ContinueOnMaxLengthMiddleware(max_continuations=1)
+    handler, _ = _handler_from(
+        [_ai("a", out=24, finish="length"), _ai("b", out=24, finish="length")]
+    )
+    req = _FakeRequest(model=_FakeModel(max_tokens=24), messages=[HumanMessage("hi")])
+
+    await mw.awrap_model_call(req, handler)
+
+    assert acc.truncated is True
+
+
+@pytest.mark.asyncio
+async def test_continuation_context_includes_partial_and_nudge():
+    mw = ContinueOnMaxLengthMiddleware(max_continuations=1)
+    seen: dict[str, Any] = {}
+
+    async def handler(request):
+        seen["messages"] = list(request.messages)
+        if len(seen["messages"]) > 1:
+            return _FakeResponse(result=[_ai("END", out=3, finish="stop")])
+        return _FakeResponse(result=[_ai("START ", out=24, finish="length")])
+
+    req = _FakeRequest(model=_FakeModel(max_tokens=24), messages=[HumanMessage("hi")])
+    resp = await mw.awrap_model_call(req, handler)
+
+    assert _text(resp) == "START END"
+    assert any(isinstance(m, AIMessage) and "START" in m.content for m in seen["messages"])
diff --git a/surfsense_backend/tests/unit/agents/multi_agent_chat/subagents/builtins/knowledge_base/test_ask_knowledge_base_tool.py b/surfsense_backend/tests/unit/agents/multi_agent_chat/subagents/builtins/knowledge_base/test_ask_knowledge_base_tool.py
new file mode 100644
index 000000000..9d43b956e
--- /dev/null
+++ b/surfsense_backend/tests/unit/agents/multi_agent_chat/subagents/builtins/knowledge_base/test_ask_knowledge_base_tool.py
@@ -0,0 +1,41 @@
+"""``ask_knowledge_base`` must self-correct, not crash the turn, on a bad call."""
+
+from __future__ import annotations
+
+import pytest
+from langchain.tools import ToolRuntime
+
+from app.agents.chat.multi_agent_chat.subagents.builtins.knowledge_base.ask_knowledge_base_tool import (
+    build_ask_knowledge_base_tool,
+)
+
+pytestmark = pytest.mark.unit
+
+
+def _runtime(tool_call_id: str) -> ToolRuntime:
+    return ToolRuntime(
+        state={},
+        context=None,
+        config={},
+        stream_writer=None,
+        tool_call_id=tool_call_id,
+        store=None,
+    )
+
+
+def test_missing_tool_call_id_returns_error_string() -> None:
+    tool = build_ask_knowledge_base_tool(kb_readonly=lambda: None)
+
+    result = tool.func("what is X?", _runtime(""))
+
+    assert isinstance(result, str)
+    assert "tool call id" in result.lower()
+
+
+async def test_missing_tool_call_id_returns_error_string_async() -> None:
+    tool = build_ask_knowledge_base_tool(kb_readonly=lambda: None)
+
+    result = await tool.coroutine("what is X?", _runtime(""))
+
+    assert isinstance(result, str)
+    assert "tool call id" in result.lower()
diff --git a/surfsense_backend/tests/unit/agents/new_chat/test_tool_call_repair.py b/surfsense_backend/tests/unit/agents/new_chat/test_tool_call_repair.py
index 1e11e39ce..28be8f642 100644
--- a/surfsense_backend/tests/unit/agents/new_chat/test_tool_call_repair.py
+++ b/surfsense_backend/tests/unit/agents/new_chat/test_tool_call_repair.py
@@ -2,15 +2,21 @@
 
 from __future__ import annotations
 
+from types import SimpleNamespace
+
 import pytest
 from langchain_core.messages import AIMessage
 
+from app.agents.chat.multi_agent_chat.main_agent.middleware.tool_call_repair.builder import (
+    build_repair_mw,
+)
 from app.agents.chat.multi_agent_chat.main_agent.middleware.tool_call_repair.middleware import (
     ToolCallNameRepairMiddleware,
 )
 from app.agents.chat.multi_agent_chat.main_agent.tools.invalid_tool import (
     INVALID_TOOL_NAME,
 )
+from app.agents.chat.multi_agent_chat.shared.feature_flags import AgentFeatureFlags
 
 pytestmark = pytest.mark.unit
 
@@ -105,6 +111,37 @@ class TestRepair:
         out = mw.after_model({"messages": []}, _FakeRuntime())
         assert out is None
 
+    def test_unbound_deepagent_builtin_routes_to_invalid(self) -> None:
+        """A router never binds FS builtins (ls/read_file/…); they must self-correct.
+
+        Previously the builder marked all deepagents builtins as "known", so a
+        ``read_file`` call passed repair and then dispatch-failed. It must route
+        to ``invalid`` instead.
+        """
+        tools = [
+            SimpleNamespace(name="search_knowledge_base"),
+            SimpleNamespace(name=INVALID_TOOL_NAME),
+        ]
+        mw = build_repair_mw(flags=AgentFeatureFlags(), tools=tools)
+        msg = AIMessage(
+            content="",
+            tool_calls=[{"name": "read_file", "args": {"path": "/x"}, "id": "1"}],
+        )
+        out = mw.after_model(_make_state(msg), _FakeRuntime())
+        assert out is not None
+        assert out["messages"][0].tool_calls[0]["name"] == INVALID_TOOL_NAME
+
+    @pytest.mark.parametrize("name", ["task", "write_todos"])
+    def test_middleware_bound_tools_stay_known(self, name: str) -> None:
+        """``task``/``write_todos`` are bound via middleware, not ``tools`` — keep them known."""
+        mw = build_repair_mw(
+            flags=AgentFeatureFlags(),
+            tools=[SimpleNamespace(name=INVALID_TOOL_NAME)],
+        )
+        msg = AIMessage(content="", tool_calls=[{"name": name, "args": {}, "id": "1"}])
+        out = mw.after_model(_make_state(msg), _FakeRuntime())
+        assert out is None  # recognized, not rewritten to invalid
+
     def test_runtime_context_extends_registered(self) -> None:
         from types import SimpleNamespace
 
diff --git a/surfsense_backend/tests/unit/routes/test_thread_awaiting_approval_guard.py b/surfsense_backend/tests/unit/routes/test_thread_awaiting_approval_guard.py
new file mode 100644
index 000000000..718baac9d
--- /dev/null
+++ b/surfsense_backend/tests/unit/routes/test_thread_awaiting_approval_guard.py
@@ -0,0 +1,71 @@
+"""A thread paused for HITL must refuse a fresh turn.
+
+The busy mutex releases on an ``interrupt()`` pause, so a paused thread reads
+as idle and ``new_chat`` / ``regenerate`` would run over the paused checkpoint,
+orphaning the pending approval. ``_raise_if_thread_awaiting_approval`` closes
+that gap by reading the checkpoint and refusing with 409.
+"""
+
+import pytest
+from fastapi import HTTPException
+from langgraph.checkpoint.memory import InMemorySaver
+from langgraph.graph import END, START, StateGraph
+from langgraph.types import interrupt
+from typing_extensions import TypedDict
+
+from app.routes.new_chat_routes import _raise_if_thread_awaiting_approval
+
+
+class _S(TypedDict, total=False):
+    messages: list
+
+
+async def _paused_checkpointer(thread_id: int) -> InMemorySaver:
+    """Run a graph that interrupts, leaving a pending interrupt in the checkpoint."""
+
+    def node(_s):
+        decision = interrupt({"action_requests": [{"name": "x", "args": {}}]})
+        return {"messages": [decision]}
+
+    g = StateGraph(_S)
+    g.add_node("n", node)
+    g.add_edge(START, "n")
+    g.add_edge("n", END)
+    cp = InMemorySaver()
+    graph = g.compile(checkpointer=cp)
+    await graph.ainvoke(
+        {"messages": []}, {"configurable": {"thread_id": str(thread_id)}}
+    )
+    return cp
+
+
+@pytest.mark.asyncio
+async def test_paused_thread_is_refused_with_409():
+    cp = await _paused_checkpointer(1)
+
+    with pytest.raises(HTTPException) as exc:
+        await _raise_if_thread_awaiting_approval(1, cp)
+
+    assert exc.value.status_code == 409
+    assert exc.value.detail["errorCode"] == "THREAD_AWAITING_APPROVAL"
+
+
+@pytest.mark.asyncio
+async def test_clean_thread_is_allowed():
+    def node(_s):
+        return {"messages": ["done"]}
+
+    g = StateGraph(_S)
+    g.add_node("n", node)
+    g.add_edge(START, "n")
+    g.add_edge("n", END)
+    cp = InMemorySaver()
+    graph = g.compile(checkpointer=cp)
+    await graph.ainvoke({"messages": []}, {"configurable": {"thread_id": "2"}})
+
+    await _raise_if_thread_awaiting_approval(2, cp)  # no raise
+
+
+@pytest.mark.asyncio
+async def test_thread_without_checkpoint_is_allowed():
+    await _raise_if_thread_awaiting_approval(999, InMemorySaver())  # no raise
diff --git a/surfsense_backend/tests/unit/services/test_truncation_detection.py b/surfsense_backend/tests/unit/services/test_truncation_detection.py
new file mode 100644
index 000000000..c746dce6f
--- /dev/null
+++ b/surfsense_backend/tests/unit/services/test_truncation_detection.py
@@ -0,0 +1,33 @@
+"""Guard the output-truncation detector.
+
+``langchain_litellm`` (0.6.4) drops ``finish_reason`` from streamed chunks, so
+a token-limit cut reaches the UI silently. The LiteLLM success callback still
+sees the real ``finish_reason`` and usage, so detection must honour both: the
+gold ``finish_reason == "length"`` signal, and a usage>=max_tokens fallback for
+paths where ``finish_reason`` is absent.
+"""
+
+from app.services.token_tracking_service import is_output_truncated
+
+
+def test_finish_reason_length_is_truncated():
+    assert is_output_truncated("length", completion_tokens=10, max_tokens=999) is True
+
+
+def test_finish_reason_stop_is_not_truncated_even_at_cap():
+    # An explicit non-length reason wins over the usage heuristic.
+    assert is_output_truncated("stop", completion_tokens=24, max_tokens=24) is False
+
+
+def test_usage_fallback_when_finish_reason_missing():
+    assert is_output_truncated(None, completion_tokens=24, max_tokens=24) is True
+    assert is_output_truncated("", completion_tokens=30, max_tokens=24) is True
+
+
+def test_under_cap_without_finish_reason_is_not_truncated():
+    assert is_output_truncated(None, completion_tokens=10, max_tokens=24) is False
+
+
+def test_no_cap_configured_cannot_infer_from_usage():
+    assert is_output_truncated(None, completion_tokens=9999, max_tokens=None) is False
+    assert is_output_truncated(None, completion_tokens=9999, max_tokens=0) is False
diff --git a/surfsense_backend/tests/unit/services/test_vercel_interrupt_id.py b/surfsense_backend/tests/unit/services/test_vercel_interrupt_id.py
new file mode 100644
index 000000000..08c9a07d6
--- /dev/null
+++ b/surfsense_backend/tests/unit/services/test_vercel_interrupt_id.py
@@ -0,0 +1,44 @@
+"""``VercelStreamingService.format_interrupt_request`` carries ``interrupt_id`` on the wire.
+
+Parent-side interrupts (doom-loop, permission asks) have no ``tool_call_id``; the
+langgraph ``Interrupt.id`` is their only stable handle, so the frontend can only
+render and resume them when it arrives on the frame.
+"""
+
+from __future__ import annotations
+
+import json
+
+import pytest
+
+from app.services.new_streaming_service import VercelStreamingService
+
+pytestmark = pytest.mark.unit
+
+
+def _payload(frame: str) -> dict:
+    body = frame.removeprefix("data: ").removesuffix("\n\n")
+    return json.loads(body)["data"]
+
+
+def test_interrupt_id_present_when_supplied() -> None:
+    frame = VercelStreamingService().format_interrupt_request(
+        {"type": "permission_ask", "action": {"tool": "search", "params": {}},
+         "context": {"permission": "doom_loop"}},
+        interrupt_id="int_7",
+    )
+    assert _payload(frame)["interrupt_id"] == "int_7"
+
+
+def test_interrupt_id_omitted_when_absent() -> None:
+    frame = VercelStreamingService().format_interrupt_request(
+        {"action_requests": [], "review_configs": []},
+    )
+    assert "interrupt_id" not in _payload(frame)
+
+
+def test_does_not_mutate_source_value() -> None:
+    """Subagent payloads pass through by reference — stamping must not touch state."""
+    value = {"action_requests": [{"name": "x", "args": {}}], "review_configs": [{}]}
+    VercelStreamingService().format_interrupt_request(value, interrupt_id="int_9")
+    assert "interrupt_id" not in value
diff --git a/surfsense_backend/tests/unit/tasks/chat/streaming/flows/resume_chat/test_resume_routing.py b/surfsense_backend/tests/unit/tasks/chat/streaming/flows/resume_chat/test_resume_routing.py
new file mode 100644
index 000000000..bd18597cb
--- /dev/null
+++ b/surfsense_backend/tests/unit/tasks/chat/streaming/flows/resume_chat/test_resume_routing.py
@@ -0,0 +1,141 @@
+"""``build_resume_routing`` must route parent-side interrupts (doom-loop / asks).
+
+Guards the bug where unstamped parent-graph interrupts were dropped on resume,
+hanging the turn.
+"""
+
+from __future__ import annotations
+
+from types import SimpleNamespace
+
+import pytest
+
+from app.tasks.chat.streaming.flows.resume_chat.resume_routing import (
+    build_resume_routing,
+)
+
+
+class _FakeAgent:
+    """Minimal stand-in exposing the ``aget_state`` the router reads."""
+
+    def __init__(self, state):
+        self._state = state
+
+    async def aget_state(self, _config):
+        return self._state
+
+
+def _doom_loop_interrupt(interrupt_id: str):
+    """A parent-side doom-loop interrupt: no ``tool_call_id``, no ``action_requests``."""
+    return SimpleNamespace(
+        id=interrupt_id,
+        value={
+            "type": "permission_ask",
+            "action": {"tool": "search_run", "params": {}},
+            "context": {"permission": "doom_loop", "threshold": 3},
+        },
+    )
+
+
+async def test_parent_side_doom_loop_interrupt_is_routable():
+    """Decision routes to the doom-loop's ``Interrupt.id`` as a raw dict, not a bundle."""
+    decision = {"type": "reject"}
+    agent = _FakeAgent(
+        SimpleNamespace(interrupts=(_doom_loop_interrupt("i-doom"),))
+    )
+
+    routing = await build_resume_routing(agent, chat_id=42, decisions=[decision])
+
+    assert routing.lg_resume_map == {"i-doom": decision}
+    # No subagent bridge for parent-side interrupts.
+    assert routing.routed_resume_value == {}
+
+
+def _permission_ask_interrupt(interrupt_id: str):
+    """A parent-side main-agent permission ask: LC HITL bundle, still no stamp."""
+    return SimpleNamespace(
+        id=interrupt_id,
+        value={
+            "type": "permission_ask",
+            "action_requests": [{"name": "create_automation", "args": {}}],
+        },
+    )
+
+
+async def test_parent_side_permission_ask_is_routable():
+    """Main-agent permission asks (unstamped) route their single decision by id."""
+    decision = {"type": "approve"}
+    agent = _FakeAgent(
+        SimpleNamespace(interrupts=(_permission_ask_interrupt("i-perm"),))
+    )
+
+    routing = await build_resume_routing(agent, chat_id=7, decisions=[decision])
+
+    assert routing.lg_resume_map == {"i-perm": decision}
+
+
+def _subagent_interrupt(interrupt_id: str, tool_call_id: str, action_count: int):
+    return SimpleNamespace(
+        id=interrupt_id,
+        value={
+            "action_requests": [{"name": "n", "args": {}}] * action_count,
+            "tool_call_id": tool_call_id,
+        },
+    )
+
+
+async def test_subagent_path_is_unchanged():
+    """Regression guard: stamped subagent interrupts still route via the bridge."""
+    decisions = [{"type": "approve"}, {"type": "reject"}]
+    agent = _FakeAgent(
+        SimpleNamespace(interrupts=(_subagent_interrupt("i-A", "tcid-A", 2),))
+    )
+
+    routing = await build_resume_routing(agent, chat_id=1, decisions=decisions)
+
+    assert routing.routed_resume_value == {"tcid-A": {"decisions": decisions}}
+    assert routing.lg_resume_map == {"i-A": {"decisions": decisions}}
+
+
+async def test_id_stamped_decisions_route_by_identity_across_boundary():
+    """Id-stamped decisions route correctly even reversed vs ``state.interrupts``."""
+    agent = _FakeAgent(
+        SimpleNamespace(
+            interrupts=(
+                _subagent_interrupt("i-A", "tcid-A", 1),
+                _subagent_interrupt("i-B", "tcid-B", 1),
+            )
+        )
+    )
+    decisions = [
+        {"type": "reject", "tool_call_id": "tcid-B"},
+        {"type": "approve", "tool_call_id": "tcid-A"},
+    ]
+
+    routing = await build_resume_routing(agent, chat_id=1, decisions=decisions)
+
+    assert routing.routed_resume_value == {
+        "tcid-A": {"decisions": [{"type": "approve", "tool_call_id": "tcid-A"}]},
+        "tcid-B": {"decisions": [{"type": "reject", "tool_call_id": "tcid-B"}]},
+    }
+    assert routing.lg_resume_map == {
+        "i-A": {"decisions": [{"type": "approve", "tool_call_id": "tcid-A"}]},
+        "i-B": {"decisions": [{"type": "reject", "tool_call_id": "tcid-B"}]},
+    }
+
+
+async def test_mixed_parent_and_subagent_pauses_fail_loud():
+    """A pause holding both interrupt kinds is unsupported and must not mis-route."""
+    agent = _FakeAgent(
+        SimpleNamespace(
+            interrupts=(
+                _subagent_interrupt("i-A", "tcid-A", 1),
+                _doom_loop_interrupt("i-doom"),
+            )
+        )
+    )
+
+    with pytest.raises(ValueError, match="mixed HITL routing"):
+        await build_resume_routing(
+            agent, chat_id=1, decisions=[{"type": "approve"}, {"type": "reject"}]
+        )
diff --git a/surfsense_backend/tests/unit/tasks/chat/streaming/test_interrupt_inspector_all.py b/surfsense_backend/tests/unit/tasks/chat/streaming/test_interrupt_inspector_all.py
index 4457f4768..6ee1ed47b 100644
--- a/surfsense_backend/tests/unit/tasks/chat/streaming/test_interrupt_inspector_all.py
+++ b/surfsense_backend/tests/unit/tasks/chat/streaming/test_interrupt_inspector_all.py
@@ -21,11 +21,110 @@ from typing_extensions import TypedDict
 from app.agents.chat.multi_agent_chat.main_agent.middleware.checkpointed_subagent_middleware.task_tool import (
     build_task_tool_with_parent_config,
 )
+from types import SimpleNamespace
+
 from app.tasks.chat.streaming.helpers.interrupt_inspector import (
+    all_interrupt_entries,
     all_interrupt_values,
+    pending_interrupt_entries_from_writes,
 )
 
 
+class TestPendingInterruptEntriesFromWrites:
+    """Read paused interrupts straight from a checkpoint's ``pending_writes``.
+
+    Powers refresh recovery: the thread-load path surfaces paused HITL cards
+    without compiling the full agent graph. Interrupts persist as writes to
+    the ``"__interrupt__"`` channel, one per paused task.
+    """
+
+    def test_extracts_value_and_id(self):
+        from langgraph.types import Interrupt
+
+        writes = [
+            ("task-1", "messages", ["ignored"]),
+            (
+                "task-2",
+                "__interrupt__",
+                [Interrupt(value={"tool_call_id": "tc-A"}, id="int-A")],
+            ),
+        ]
+
+        assert pending_interrupt_entries_from_writes(writes) == [
+            ({"tool_call_id": "tc-A"}, "int-A")
+        ]
+
+    def test_handles_scalar_value_not_wrapped_in_list(self):
+        from langgraph.types import Interrupt
+
+        writes = [("t", "__interrupt__", Interrupt(value={"a": 1}, id="i-1"))]
+
+        assert pending_interrupt_entries_from_writes(writes) == [({"a": 1}, "i-1")]
+
+    def test_skips_non_interrupt_channels_and_non_dict_values(self):
+        from langgraph.types import Interrupt
+
+        writes = [
+            ("t", "messages", [Interrupt(value={"a": 1}, id="x")]),
+            ("t", "__interrupt__", [Interrupt(value="not-a-dict", id="y")]),
+        ]
+
+        assert pending_interrupt_entries_from_writes(writes) == []
+
+    def test_none_input_returns_empty(self):
+        assert pending_interrupt_entries_from_writes(None) == []
+
+
+class TestAllInterruptEntries:
+    """``all_interrupt_entries`` pairs each interrupt value with its ``Interrupt.id``.
+
+    The id is what lets parent-side interrupts (doom-loop, permission asks) —
+    which carry no ``tool_call_id`` — be addressed on the wire and on resume.
+    """
+
+    def test_pairs_value_with_id_from_state_interrupts(self):
+        state = SimpleNamespace(
+            interrupts=(
+                SimpleNamespace(id="i-1", value={"context": {"permission": "doom_loop"}}),
+                SimpleNamespace(id="i-2", value={"tool_call_id": "tcid-A"}),
+            )
+        )
+
+        assert all_interrupt_entries(state) == [
+            ({"context": {"permission": "doom_loop"}}, "i-1"),
+            ({"tool_call_id": "tcid-A"}, "i-2"),
+        ]
+
+    def test_prefers_task_bucket_interrupts(self):
+        state = SimpleNamespace(
+            tasks=(
+                SimpleNamespace(interrupts=(SimpleNamespace(id="t-1", value={"a": 1}),)),
+            ),
+            interrupts=(SimpleNamespace(id="ignored", value={"b": 2}),),
+        )
+
+        assert all_interrupt_entries(state) == [({"a": 1}, "t-1")]
+
+    def test_skips_non_dict_values(self):
+        state = SimpleNamespace(
+            interrupts=(SimpleNamespace(id="i-1", value="not-a-dict"),)
+        )
+
+        assert all_interrupt_entries(state) == []
+
+    def test_id_missing_is_none(self):
+        state = SimpleNamespace(interrupts=(SimpleNamespace(value={"a": 1}),))
+
+        assert all_interrupt_entries(state) == [({"a": 1}, None)]
+
+    def test_values_helper_derives_from_entries(self):
+        state = SimpleNamespace(
+            interrupts=(SimpleNamespace(id="i-1", value={"a": 1}),)
+        )
+
+        assert all_interrupt_values(state) == [{"a": 1}]
+
+
 class _SubState(TypedDict, total=False):
     messages: list
 
diff --git a/surfsense_web/app/dashboard/[workspace_id]/new-chat/[[...chat_id]]/page.tsx b/surfsense_web/app/dashboard/[workspace_id]/new-chat/[[...chat_id]]/page.tsx
index 70cf4c8e0..d2e804240 100644
--- a/surfsense_web/app/dashboard/[workspace_id]/new-chat/[[...chat_id]]/page.tsx
+++ b/surfsense_web/app/dashboard/[workspace_id]/new-chat/[[...chat_id]]/page.tsx
@@ -65,7 +65,7 @@ import {
 import { extractMentionedDocuments } from "@/lib/chat/stream-engine/helpers";
 import { chatStreamStore } from "@/lib/chat/stream-engine/store";
 import { useChatStream } from "@/lib/chat/stream-engine/use-chat-stream";
-import type { ThreadRecord } from "@/lib/chat/thread-persistence";
+import { getPendingInterrupts, type ThreadRecord } from "@/lib/chat/thread-persistence";
 import {
 	extractUserTurnForNewChatApi,
 	type NewChatUserImagePayload,
@@ -356,6 +356,50 @@ export default function NewChatPage() {
 		threadMessagesQuery.data,
 	]);
 
+	// Rebuild paused HITL cards after a refresh. The live overlay lives only in
+	// module RAM, so on reload we ask the backend for interrupts still pending
+	// in the checkpoint and repopulate the store (which re-pins the thread).
+	const reconstructedInterruptsRef = useRef<number | null>(null);
+	useEffect(() => {
+		if (!activeThreadId || isRunning || !threadMessagesQuery.data) return;
+		if (reconstructedInterruptsRef.current === activeThreadId) return;
+		if (chatStreamStore.getPendingInterrupts(activeThreadId).length > 0) return;
+
+		reconstructedInterruptsRef.current = activeThreadId;
+		const threadId = activeThreadId;
+		void getPendingInterrupts(threadId)
+			.then((resp) => {
+				if (resp.assistant_message_id == null || resp.pending_interrupts.length === 0) return;
+				if (chatStreamStore.getPendingInterrupts(threadId).length > 0) return;
+				const assistantMsgId = `msg-${resp.assistant_message_id}`;
+				const reconstructed = resp.pending_interrupts
+					.map((interruptData) => {
+						const interruptId = String(
+							interruptData.tool_call_id ?? interruptData.interrupt_id ?? ""
+						);
+						const actionRequests = Array.isArray(interruptData.action_requests)
+							? interruptData.action_requests
+							: [];
+						return {
+							interruptId,
+							threadId,
+							assistantMsgId,
+							interruptData,
+							bundleToolCallIds: actionRequests.map((_a, i) => `reconstructed-${interruptId}-${i}`),
+						} satisfies PendingInterruptState;
+					})
+					.filter((p) => p.interruptId);
+				if (reconstructed.length > 0) {
+					chatStreamStore.setPendingInterrupts(threadId, () => reconstructed);
+				}
+			})
+			.catch((err) => {
+				// Non-fatal: the thread still renders; the card just won't reappear.
+				console.error("[NewChatPage] Failed to load pending interrupts:", err);
+				reconstructedInterruptsRef.current = null;
+			});
+	}, [activeThreadId, isRunning, threadMessagesQuery.data]);
+
 	useEffect(() => {
 		const loadError = threadDetailQuery.error ?? threadMessagesQuery.error;
 		if (!activeThreadId || !loadError) return;
@@ -628,6 +672,9 @@ export default function NewChatPage() {
 			const incoming = detail.decisions;
 			if (incoming.length === 0) return;
 			const tcIds = pendingInterrupts.flatMap((p) => p.bundleToolCallIds);
+			const parentInterruptIds = pendingInterrupts.flatMap((p) =>
+				p.bundleToolCallIds.map(() => p.interruptId)
+			);
 			const N = tcIds.length;
 
 			if (incoming.length !== N) {
@@ -638,18 +685,19 @@ export default function NewChatPage() {
 			}
 
 			const byTcId = new Map<string, (typeof incoming)[number]>();
-			const submittedDecisions: typeof incoming = [];
+			const submittedDecisions: Array<(typeof incoming)[number] & { tool_call_id: string }> = [];
 			for (let i = 0; i < tcIds.length; i++) {
 				const tcId = tcIds[i];
+				const parentId = parentInterruptIds[i];
 				const decision = incoming[i];
-				if (tcId === undefined || decision === undefined) {
+				if (tcId === undefined || parentId === undefined || decision === undefined) {
 					toast.error(
 						`Cannot resume: ${incoming.length} decision(s) submitted for ${N} pending actions.`
 					);
 					return;
 				}
 				byTcId.set(tcId, decision);
-				submittedDecisions.push(decision);
+				submittedDecisions.push({ ...decision, tool_call_id: parentId });
 			}
 
 			const targetAssistantMsgId = pendingInterrupts[0].assistantMsgId;
diff --git a/surfsense_web/features/chat-messages/hitl/approval/hitl-approval-card.tsx b/surfsense_web/features/chat-messages/hitl/approval/hitl-approval-card.tsx
index 8aa8c7499..38781b228 100644
--- a/surfsense_web/features/chat-messages/hitl/approval/hitl-approval-card.tsx
+++ b/surfsense_web/features/chat-messages/hitl/approval/hitl-approval-card.tsx
@@ -9,6 +9,7 @@ import {
 	getToolComponent,
 	type TimelineToolProps,
 } from "@/features/chat-messages/timeline/tool-registry";
+import { isDoomLoopInterrupt } from "../approval-cards";
 import type {
 	HitlDecision,
 	InterruptActionRequest,
@@ -161,7 +162,12 @@ export const HitlApprovalCard: FC<{
 	const stagedDecision = decisions[currentStep];
 	const sliced = sliceForStep(interruptData, action, reviewConfig, stagedDecision);
 
-	const Body = getToolComponent(action.name) ?? FallbackToolBody;
+	// Doom-loop's ``action.name`` is the *stuck* tool, not an approval target,
+	// so its registered body (or ``NullTimelineBody``) would suppress the card.
+	// Route it through the HITL-aware fallback, which renders ``DoomLoopApproval``.
+	const Body = isDoomLoopInterrupt(sliced)
+		? FallbackToolBody
+		: (getToolComponent(action.name) ?? FallbackToolBody);
 	const bodyProps: TimelineToolProps = {
 		// Per-step key remounts the body on navigation so per-tool
 		// internal state (useHitlPhase, edit drafts) doesn't bleed
diff --git a/surfsense_web/lib/chat/stream-engine/engine.ts b/surfsense_web/lib/chat/stream-engine/engine.ts
index 34536efc1..0c0938729 100644
--- a/surfsense_web/lib/chat/stream-engine/engine.ts
+++ b/surfsense_web/lib/chat/stream-engine/engine.ts
@@ -671,11 +671,13 @@ export async function startNewChat(ctx: EngineContext, message: AppendMessage):
 								: m
 						)
 					);
-					// ``tool_call_id`` is stamped on the backend by
-					// ``checkpointed_subagent_middleware``. Without it we can't
-					// address the paused subagent on resume — skip rather than
-					// fabricate a synthetic key.
-					const interruptId = String(interruptData.tool_call_id ?? "");
+					// Subagent interrupts carry ``tool_call_id``; parent-side ones
+					// (doom-loop, permission asks) carry only the langgraph
+					// ``interrupt_id``. Either addresses the pause on resume — skip
+					// only when neither is present.
+					const interruptId = String(
+						interruptData.tool_call_id ?? interruptData.interrupt_id ?? ""
+					);
 					if (interruptId) {
 						const incoming: PendingInterruptState = {
 							interruptId,
@@ -822,6 +824,7 @@ export async function resumeChat(
 		type: string;
 		message?: string;
 		edited_action?: { name: string; args: Record<string, unknown> };
+		tool_call_id?: string;
 	}>
 ): Promise<void> {
 	const { workspaceId, threadId } = ctx;
@@ -1018,7 +1021,9 @@ export async function resumeChat(
 						)
 					);
 					{
-						const interruptId = String(interruptData.tool_call_id ?? "");
+						const interruptId = String(
+							interruptData.tool_call_id ?? interruptData.interrupt_id ?? ""
+						);
 						if (interruptId) {
 							const incoming: PendingInterruptState = {
 								interruptId,
diff --git a/surfsense_web/lib/chat/stream-pipeline.ts b/surfsense_web/lib/chat/stream-pipeline.ts
index a6899ffab..d928f091b 100644
--- a/surfsense_web/lib/chat/stream-pipeline.ts
+++ b/surfsense_web/lib/chat/stream-pipeline.ts
@@ -1,3 +1,4 @@
+import { toast } from "sonner";
 import {
 	addStepSeparator,
 	addToolCall,
@@ -180,6 +181,12 @@ export function processSharedStreamEvent(
 		}
 
 		case "data-token-usage":
+			if (parsed.data.truncated) {
+				toast.warning("Response was cut off — the model hit its output-token limit.", {
+					duration: Infinity,
+					closeButton: true,
+				});
+			}
 			context.onTokenUsage?.(parsed.data);
 			return true;
 
diff --git a/surfsense_web/lib/chat/streaming-state.ts b/surfsense_web/lib/chat/streaming-state.ts
index 5bad04319..5817f4ffc 100644
--- a/surfsense_web/lib/chat/streaming-state.ts
+++ b/surfsense_web/lib/chat/streaming-state.ts
@@ -644,6 +644,8 @@ export type SSEEvent =
 					total_tokens: number;
 					cost_micros?: number;
 				}>;
+				/** Some generation in the turn hit its output-token cap. */
+				truncated?: boolean;
 			};
 	  }
 	| { type: "error"; message: string; errorCode?: string; diagnostic?: string };
diff --git a/surfsense_web/lib/chat/thread-persistence.ts b/surfsense_web/lib/chat/thread-persistence.ts
index 006206c64..cc2848550 100644
--- a/surfsense_web/lib/chat/thread-persistence.ts
+++ b/surfsense_web/lib/chat/thread-persistence.ts
@@ -202,6 +202,26 @@ export async function getThreadFull(threadId: number): Promise<ThreadRecord> {
 	return baseApiService.get<ThreadRecord>(`/api/v1/threads/${threadId}/full`);
 }
 
+export interface PendingInterruptsResponse {
+	/** The paused turn's assistant row; the reconstructed card reattaches here. */
+	assistant_message_id: number | null;
+	/** Each entry mirrors the ``data-interrupt-request`` SSE payload. */
+	pending_interrupts: Array<Record<string, unknown>>;
+}
+
+/**
+ * Fetch the thread's paused HITL interrupts from the LangGraph checkpoint.
+ *
+ * The live approval card lives only in ``chatStreamStore`` (module RAM), so a
+ * page refresh loses it while the backend stays paused. Called on thread load
+ * to rebuild the card.
+ */
+export async function getPendingInterrupts(threadId: number): Promise<PendingInterruptsResponse> {
+	return baseApiService.get<PendingInterruptsResponse>(
+		`/api/v1/threads/${threadId}/pending-interrupts`
+	);
+}
+
 /**
  * Regeneration request parameters
  */