fix(agents): make librarian failures structured and user-safe

- run_librarian / run_librarian_stream raise AgentError instead of
  returning/yielding error text as normal output; detail stays in logs
- delegate_to_* wrappers now put a curated butler-toned sentence in
  DelegationResult.output on failure and never expose str(e), so
  streaming's error branch is reachable and honest
- _execute_single_delegation propagates success; direct delegation only
  records delegate_to_* as called when the expert actually succeeded
- librarian tools return user-safe messages instead of
  'Error searching: {e}' strings that leaked internal URLs into
  synthesis; coordination stream errors are curated as well
- ruff cleanups (TYPE_CHECKING forward refs, B904, unused locals) in
  the touched files to keep them lint-clean

Co-Authored-By: Claude Fable 5 <noreply@anthropic.com>

CHANGELOG.md

@@ -9,6 +9,8 @@ and this project adheres to [Semantic Versioning](https://semver.org/spec/v2.0.0
 
 ### Fixed
 
+- **Honest expert failures** - `run_librarian`/`run_librarian_stream` now raise a structured `AgentError` instead of returning error text as if it were research output, so delegation correctly reports `success=False` and the streaming error branch is reachable. Failures surface to the user as curated butler-toned sentences; exception detail (including internal URLs) stays in the logs only. Librarian tool errors no longer leak `str(e)` into synthesis
+
 - **HybridRAG response mapping** - The librarian client now parses the field names library-desk actually returns (`source_type`/`sources`, `rrf_score`, `context`, per-item `related_dossiers`, synonyms nested in the `keywords` dict); previously every result rendered as "unknown (score: 0.00)". Source icons now key off the per-item `sources` list. Requests no longer send zero limits (the service rejects them with 422); legs are disabled via `enable_*` flags. Pinned by a contract test against a recorded live response (`tests/agents/librarian/fixtures/`)
 
 ## [2.3.0] - 2026-07-13

src/agents/coordination.py

@@ -10,7 +10,8 @@ based on Steward recommendations. Handles:
 """
 import asyncio
 import time
-from typing import Any, AsyncGenerator, Optional
+from collections.abc import AsyncGenerator
+from typing import Any
 
 from src.agents.librarian import run_librarian, run_librarian_stream
 from src.agents.protocol import (
@@ -22,7 +23,6 @@ from src.agents.protocol import (
     CoordinationResult,
     DelegationIntent,
     DelegationReason,
-    ToolCallRecord,
 )
 from src.core.household_registry import get_household_registry
 from src.core.logging_config import get_logger
@@ -87,7 +87,7 @@ class CoordinationEngine:
         self,
         intent: DelegationIntent,
         context: str = "",
-        message_history: Optional[list[Any]] = None,
+        message_history: list[Any] | None = None,
     ) -> AgentResponse:
         """
         Execute a single delegation to an expert agent.
@@ -166,7 +166,7 @@ class CoordinationEngine:
                 duration_ms=duration_ms,
             )
 
-        except asyncio.TimeoutError:
+        except TimeoutError as e:
             duration_ms = int((time.time() - start_time) * 1000)
             logger.error(
                 "delegation_timeout",
@@ -176,7 +176,7 @@ class CoordinationEngine:
             raise AgentTimeoutError(
                 f"Agent '{agent_name}' timed out after {duration_ms}ms",
                 agent_name=agent_name,
-            )
+            ) from e
 
         except Exception as e:
             duration_ms = int((time.time() - start_time) * 1000)
@@ -198,7 +198,7 @@ class CoordinationEngine:
         self,
         intent: DelegationIntent,
         context: str = "",
-        message_history: Optional[list[Any]] = None,
+        message_history: list[Any] | None = None,
     ) -> AsyncGenerator[str, None]:
         """
         Execute a delegation with streaming output.
@@ -242,19 +242,23 @@ class CoordinationEngine:
             logger.info("delegation_stream_completed", agent=agent_name)
 
         except Exception as e:
+            # Exception detail stays in the logs; yield a curated
+            # user-safe sentence instead of leaking internals.
+            from src.agents.delegation import get_think_message
+
             logger.error(
                 "delegation_stream_error",
                 agent=agent_name,
                 error=str(e),
                 exc_info=True,
             )
-            yield f"\n\n[Error from {agent_name}: {str(e)}]"
+            yield "\n\n" + get_think_message(agent_name, intent.task, "error")
 
     async def coordinate(
         self,
         intents: list[DelegationIntent],
         context: str = "",
-        message_history: Optional[list[Any]] = None,
+        message_history: list[Any] | None = None,
     ) -> CoordinationResult:
         """
         Coordinate execution of multiple delegations.
@@ -329,7 +333,7 @@ class CoordinationEngine:
 
 
 # Global coordination engine instance
-_coordination_engine: Optional[CoordinationEngine] = None
+_coordination_engine: CoordinationEngine | None = None
 
 
 def get_coordination_engine() -> CoordinationEngine:
@@ -344,7 +348,7 @@ async def delegate_to_librarian(
     task: str,
     context: str = "",
     reason: DelegationReason = DelegationReason.DOMAIN_EXPERTISE,
-    message_history: Optional[list[Any]] = None,
+    message_history: list[Any] | None = None,
 ) -> AgentResponse:
     """
     Convenience function to delegate a task to The Librarian.
@@ -377,7 +381,7 @@ async def delegate_to_librarian(
 async def delegate_to_librarian_stream(
     task: str,
     context: str = "",
-    message_history: Optional[list[Any]] = None,
+    message_history: list[Any] | None = None,
 ) -> AsyncGenerator[str, None]:
     """
     Convenience function to delegate to Librarian with streaming.

src/agents/delegation.py

@@ -8,12 +8,12 @@ returns a structured result for synthesis.
 This implements the agent-as-tool pattern recommended by PydanticAI:
 agents call other agents via tool wrappers, keeping each agent focused.
 """
+from collections.abc import AsyncGenerator
 from dataclasses import dataclass, field
 from enum import Enum
-from typing import AsyncGenerator, Callable, Optional, Any
 
 from src.core.logging_config import get_logger
-from src.core.tracing import trace_span, SpanType
+from src.core.tracing import SpanType, trace_span
 
 logger = get_logger(__name__)
 
@@ -167,7 +167,7 @@ class DelegationTask:
     action: str = ""
     priority: int = 0
     depends_on: list[str] = field(default_factory=list)
-    result: Optional[str] = None
+    result: str | None = None
     task_id: str = ""
 
     def __post_init__(self):
@@ -186,14 +186,16 @@ class DelegationResult:
         expert_name: Which expert handled the task
         task: Original task description
         success: Whether the delegation succeeded
-        output: Expert's response/findings
-        error: Error message if failed
+        output: Expert's response/findings. On failure this holds a
+            curated, user-safe butler sentence (never exception detail)
+        error: Short user-safe error label if failed. Exception detail
+            stays in the logs only
     """
     expert_name: str
     task: str
     success: bool
     output: str
-    error: Optional[str] = None
+    error: str | None = None
 
 
 async def delegate_to_librarian(
@@ -285,12 +287,15 @@ async def delegate_to_librarian(
                 span.metadata["success"] = False
                 span.details["error"] = str(e)
 
+            # Exception detail stays in the logs; the user-facing output
+            # is a curated butler sentence so internals never leak into
+            # synthesis.
             return DelegationResult(
                 expert_name="librarian",
                 task=task,
                 success=False,
-                output="",
-                error=str(e),
+                output=get_think_message("librarian", task, "error"),
+                error="The Librarian was unable to complete the task.",
             )
 
 
@@ -383,12 +388,13 @@ async def delegate_to_biographer(
                 span.metadata["success"] = False
                 span.details["error"] = str(e)
 
+            # Exception detail stays in the logs only.
             return DelegationResult(
                 expert_name="biographer",
                 task=task,
                 success=False,
-                output="",
-                error=str(e),
+                output=get_think_message("biographer", task, "error"),
+                error="The Biographer was unable to complete the task.",
             )
 
 
@@ -480,12 +486,13 @@ async def delegate_to_housekeeper(
                 span.metadata["success"] = False
                 span.details["error"] = str(e)
 
+            # Exception detail stays in the logs only.
             return DelegationResult(
                 expert_name="housekeeper",
                 task=task,
                 success=False,
-                output="",
-                error=str(e),
+                output=get_think_message("housekeeper", task, "error"),
+                error="The Housekeeper was unable to complete the task.",
             )
 
 

src/agents/librarian/agent.py

@@ -7,7 +7,7 @@ the library-desk API, offering:
 - Wiki and document management
 - Semantic search and knowledge graph exploration
 """
-from typing import Any, Optional
+from typing import Any
 
 from pydantic_ai import Agent
 
@@ -27,7 +27,7 @@ from src.agents.librarian.tools import (
     smart_create_wiki_page,
     update_wiki_page,
 )
-from src.core.config import config
+from src.agents.protocol import AgentError
 from src.core.logging_config import get_logger
 
 logger = get_logger(__name__)
@@ -138,7 +138,7 @@ If a tool fails or you cannot access a data source:
 """
 
 # Lazy initialization to avoid connection issues during imports
-_librarian_agent: Optional[Agent[None, str]] = None
+_librarian_agent: Agent[None, str] | None = None
 
 
 def _create_librarian_agent() -> Agent[None, str]:
@@ -204,7 +204,7 @@ def get_librarian_agent() -> Agent[None, str]:
 async def run_librarian(
     task: str,
     context: str = "",
-    message_history: Optional[list[Any]] = None,
+    message_history: list[Any] | None = None,
 ) -> str:
     """
     Execute a research task with The Librarian.
@@ -220,6 +220,10 @@ async def run_librarian(
     Returns:
         Research results and findings
 
+    Raises:
+        AgentError: If the research task fails. Exception detail is
+            logged here; callers map the failure to a user-safe message.
+
     Example:
         result = await run_librarian(
             task="Find information about Docker networking",
@@ -255,19 +259,23 @@ async def run_librarian(
         return result.output
 
     except Exception as e:
+        # Full detail stays in the logs; callers receive a structured
+        # failure instead of error text masquerading as research output.
         logger.error(
             "librarian_task_error",
             task=task[:50],
             error=str(e),
             exc_info=True,
         )
-        return f"The Librarian encountered an error: {str(e)}"
+        raise AgentError(
+            "Research task failed", agent_name="librarian"
+        ) from e
 
 
 async def run_librarian_stream(
     task: str,
     context: str = "",
-    message_history: Optional[list[Any]] = None,
+    message_history: list[Any] | None = None,
 ):
     """
     Execute a research task with streaming output.
@@ -282,6 +290,10 @@ async def run_librarian_stream(
     Yields:
         str: Text deltas from the response
 
+    Raises:
+        AgentError: If the research task fails. Exception detail is
+            logged here; callers map the failure to a user-safe message.
+
     Example:
         async for delta in run_librarian_stream("Find Docker docs"):
             print(delta, end="", flush=True)
@@ -309,10 +321,14 @@ async def run_librarian_stream(
         logger.info("librarian_stream_completed", task=task[:50])
 
     except Exception as e:
+        # Full detail stays in the logs; raise instead of yielding error
+        # text into the stream as if it were research output.
         logger.error(
             "librarian_stream_error",
             task=task[:50],
             error=str(e),
             exc_info=True,
         )
-        yield f"\n\nThe Librarian encountered an error: {str(e)}"
+        raise AgentError(
+            "Research task failed", agent_name="librarian"
+        ) from e

src/agents/librarian/tools.py

@@ -111,7 +111,7 @@ async def hybrid_search(
 
     except Exception as e:
         logger.error("librarian_hybrid_search_error", error=str(e), query=query)
-        return f"Error searching: {str(e)}"
+        return "I was unable to search the knowledge archives; the search service did not respond properly."
 
 
 # ============================================================================
@@ -159,7 +159,7 @@ async def search_wiki(
 
     except Exception as e:
         logger.error("librarian_wiki_search_error", error=str(e))
-        return f"Error searching wiki: {str(e)}"
+        return "I was unable to search the wiki at this time."
 
 
 async def get_wiki_page(
@@ -202,7 +202,7 @@ async def get_wiki_page(
 
     except Exception as e:
         logger.error("librarian_get_page_error", error=str(e), page_id=page_id)
-        return f"Error getting page {page_id}: {str(e)}"
+        return f"I was unable to retrieve wiki page {page_id}."
 
 
 async def list_dossiers() -> str:
@@ -236,7 +236,7 @@ async def list_dossiers() -> str:
 
     except Exception as e:
         logger.error("librarian_list_dossiers_error", error=str(e))
-        return f"Error listing dossiers: {str(e)}"
+        return "I was unable to retrieve the list of dossiers."
 
 
 async def get_dossier_pages(
@@ -277,7 +277,7 @@ async def get_dossier_pages(
 
     except Exception as e:
         logger.error("librarian_get_dossier_error", error=str(e))
-        return f"Error getting dossier: {str(e)}"
+        return f"I was unable to retrieve the dossier '{dossier_name}'."
 
 
 # ============================================================================
@@ -326,7 +326,7 @@ async def semantic_search(
 
     except Exception as e:
         logger.error("librarian_semantic_search_error", error=str(e))
-        return f"Error in semantic search: {str(e)}"
+        return "I was unable to complete the semantic search."
 
 
 # ============================================================================
@@ -379,7 +379,7 @@ async def explore_knowledge_graph(
 
     except Exception as e:
         logger.error("librarian_explore_graph_error", error=str(e))
-        return f"Error exploring knowledge graph: {str(e)}"
+        return "I was unable to explore the knowledge graph."
 
 
 async def find_related_entities(
@@ -450,7 +450,7 @@ async def find_related_entities(
 
     except Exception as e:
         logger.error("librarian_find_related_error", error=str(e))
-        return f"Error finding related entities: {str(e)}"
+        return f"I was unable to look up entities related to '{entity_name}'."
 
 
 # ============================================================================
@@ -533,7 +533,7 @@ async def search_web(
 
     except Exception as e:
         logger.error("librarian_web_search_error", error=str(e), query=query)
-        return f"Error searching web: {str(e)}"
+        return "I was unable to search the web at this time."
 
 
 async def read_url(
@@ -609,7 +609,7 @@ async def read_url(
 
     except Exception as e:
         logger.error("librarian_read_url_error", error=str(e), url=url)
-        return f"Error reading URL: {str(e)}"
+        return f"I was unable to read the page at {url}."
 
 
 async def read_urls_batch(
@@ -683,7 +683,7 @@ async def read_urls_batch(
 
     except Exception as e:
         logger.error("librarian_read_urls_batch_error", error=str(e))
-        return f"Error reading URLs: {str(e)}"
+        return "I was unable to read the requested pages."
 
 
 # ============================================================================
@@ -766,7 +766,7 @@ async def update_wiki_page(
 
     except Exception as e:
         logger.error("librarian_update_page_error", error=str(e), page_id=page_id)
-        return f"Error updating page {page_id}: {str(e)}"
+        return f"I was unable to update wiki page {page_id}."
 
 
 async def create_wiki_page(
@@ -841,7 +841,7 @@ async def create_wiki_page(
 
     except Exception as e:
         logger.error("librarian_create_page_error", error=str(e), title=title)
-        return f"Error creating page: {str(e)}"
+        return f"I was unable to create the page '{title}'."
 
 
 async def smart_create_wiki_page(
@@ -930,7 +930,7 @@ async def smart_create_wiki_page(
 
     except Exception as e:
         logger.error("librarian_smart_create_error", error=str(e), topic=topic)
-        return f"Error creating page about '{topic}': {str(e)}"
+        return f"I was unable to create a page about '{topic}'."
 
 
 # ============================================================================

src/responses/service.py

@@ -6,32 +6,32 @@ Tracks conversation history for analytics and future vector memory.
 Integrates with Steward preprocessing for Phase 2 two-tier architecture.
 """
 
-import time
+import asyncio
+import re
 import secrets
-from typing import AsyncGenerator
+import time
+from collections.abc import AsyncGenerator
 
+from src.agents.delegation import get_think_message
 from src.agents.registry import ModelRegistry
+from src.agents.steward.schemas import StewardRecommendation
+from src.core.context import current_conversation, current_user, get_default_user
+from src.core.logging_config import get_logger
+from src.core.preprocessing import preprocess_request
+from src.core.tool_tracking import ToolCallTracker
+from src.core.tracing import SpanType, end_trace, start_span, start_trace
+from src.responses.context import ContextWindow
+from src.responses.history import ConversationHistory
 from src.responses.schemas import (
+    FunctionCallOutputItem,
+    MessageOutputItem,
+    OutputTextContent,
+    ReasoningOutputItem,
     Response,
     ResponseRequest,
     ResponseUsage,
-    MessageOutputItem,
-    ReasoningOutputItem,
-    FunctionCallOutputItem,
-    OutputTextContent,
 )
 from src.responses.streaming import StreamingCoordinator
-from src.responses.history import ConversationHistory
-from src.responses.context import ContextWindow
-from src.core.preprocessing import preprocess_request
-from src.core.tool_tracking import ToolCallTracker
-from src.core.logging_config import get_logger
-from src.core.tracing import start_trace, end_trace, start_span, SpanType
-from src.core.context import current_user, current_conversation, get_default_user
-from src.agents.steward.schemas import StewardRecommendation
-
-import re
-import asyncio
 
 logger = get_logger(__name__)
 
@@ -63,7 +63,7 @@ async def _execute_single_delegation(
     agent_name: str,
     task: str,
     tracker: "ToolCallTracker",
-) -> tuple[str, str]:
+) -> tuple[str, str, bool]:
     """
     Execute a single delegation to an agent.
 
@@ -73,7 +73,8 @@ async def _execute_single_delegation(
         tracker: Tool call tracker
 
     Returns:
-        tuple: (agent_name, result_summary)
+        tuple: (agent_name, result_summary, success). On failure the
+            result summary is a curated user-safe sentence.
     """
     import time
     start_time = time.time()
@@ -83,24 +84,24 @@ async def _execute_single_delegation(
         result = await delegate_to_biographer(task=task)
         duration = time.time() - start_time
         await tracker.track_call("delegate_to_biographer", duration)
-        return (agent_name, result.output)
+        return (agent_name, result.output, result.success)
 
     elif agent_name == "librarian":
         from src.agents.delegation import delegate_to_librarian
         result = await delegate_to_librarian(task=task)
         duration = time.time() - start_time
         await tracker.track_call("delegate_to_librarian", duration)
-        return (agent_name, result.output)
+        return (agent_name, result.output, result.success)
 
     elif agent_name == "housekeeper":
         from src.agents.delegation import delegate_to_housekeeper
         result = await delegate_to_housekeeper(task=task)
         duration = time.time() - start_time
         await tracker.track_call("delegate_to_housekeeper", duration)
-        return (agent_name, result.output)
+        return (agent_name, result.output, result.success)
 
     else:
-        return (agent_name, f"Unknown agent: {agent_name}")
+        return (agent_name, f"Unknown agent: {agent_name}", False)
 
 
 async def _handle_text_delegation(
@@ -175,13 +176,24 @@ async def _handle_text_delegation(
             ]
             results = await asyncio.gather(*tasks, return_exceptions=True)
 
-            # Combine results
+            # Combine results (failures carry curated user-safe sentences)
             summaries = []
-            for agent_name, result in results:
-                if isinstance(result, Exception):
-                    summaries.append(f"**{agent_name}**: Error - {result}")
+            for (agent, task), item in zip(matches, results, strict=False):
+                agent_name = agent.lower()
+                if isinstance(item, BaseException):
+                    logger.error(
+                        "delegation_failed",
+                        agent=agent_name,
+                        error=str(item),
+                        conversation_id=conversation_id,
+                    )
+                    summaries.append(
+                        f"**{agent_name}**: "
+                        f"{get_think_message(agent_name, task, 'error')}"
+                    )
                 else:
-                    summaries.append(f"**{agent_name}**: {result}")
+                    _, output, _ = item
+                    summaries.append(f"**{agent_name}**: {output}")
 
             return "\n\n".join(summaries)
 
@@ -197,20 +209,19 @@ async def _handle_text_delegation(
                     conversation_id=conversation_id,
                 )
                 try:
-                    _, result = await _execute_single_delegation(
+                    _, output, _ = await _execute_single_delegation(
                         agent_name, task, tracker
                     )
-                    summaries.append(result)
+                    summaries.append(output)
                 except Exception as e:
                     logger.error(
                         "delegation_failed",
                         agent=agent_name,
                         error=str(e),
                         conversation_id=conversation_id,
+                        exc_info=True,
                     )
-                    summaries.append(
-                        f"I apologize, sir. Delegation to {agent_name} failed: {e}"
-                    )
+                    summaries.append(get_think_message(agent_name, task, "error"))
 
             return "\n\n".join(summaries)
 
@@ -219,8 +230,9 @@ async def _handle_text_delegation(
             "text_delegation_failed",
             error=str(e),
             conversation_id=conversation_id,
+            exc_info=True,
         )
-        return f"I apologize, sir. I encountered an error processing delegations: {e}"
+        return "I apologize, sir. I was unable to complete the requested delegations."
 
 
 async def _direct_delegation(
@@ -254,13 +266,14 @@ async def _direct_delegation(
     results = []
     for agent in recommendation.recommended_capabilities:
         try:
-            agent_name, result = await _execute_single_delegation(
+            agent_name, result, success = await _execute_single_delegation(
                 agent, user_message, tracker
             )
             results.append(result)
             logger.info(
                 "direct_delegation_complete",
                 agent=agent_name,
+                success=success,
                 result_preview=result[:100] if result else "empty",
                 conversation_id=conversation_id,
             )
@@ -270,8 +283,9 @@ async def _direct_delegation(
                 agent=agent,
                 error=str(e),
                 conversation_id=conversation_id,
+                exc_info=True,
             )
-            results.append(f"I apologize, sir. Delegation to {agent} failed: {e}")
+            results.append(get_think_message(agent, user_message, "error"))
 
     return "\n\n".join(results) if results else "I apologize, sir. No delegation results available."
 
@@ -309,15 +323,17 @@ async def _direct_delegation_with_results(
 
     for agent in recommendation.recommended_capabilities:
         try:
-            agent_name, result = await _execute_single_delegation(
+            agent_name, result, success = await _execute_single_delegation(
                 agent, user_message, tracker
             )
             expert_results[agent_name] = result
-            tools_called.append(f"delegate_to_{agent_name}")
+            if success:
+                tools_called.append(f"delegate_to_{agent_name}")
 
             logger.info(
                 "direct_delegation_result",
                 agent=agent_name,
+                success=success,
                 result_preview=result[:100] if result else "empty",
                 conversation_id=conversation_id,
             )
@@ -327,8 +343,9 @@ async def _direct_delegation_with_results(
                 agent=agent,
                 error=str(e),
                 conversation_id=conversation_id,
+                exc_info=True,
             )
-            expert_results[agent] = f"Error: {e}"
+            expert_results[agent] = get_think_message(agent, user_message, "error")
 
     return {
         "tools_called": tools_called,
@@ -439,7 +456,7 @@ async def create_response(request: ResponseRequest) -> Response:
     user_input = _extract_user_input(request.input)
 
     # Start trace
-    trace = start_trace(
+    start_trace(
         conversation_id=conversation_id,
         user=effective_user,
         request={
@@ -451,7 +468,7 @@ async def create_response(request: ResponseRequest) -> Response:
     )
 
     # Start service span
-    service_span = start_span(
+    start_span(
         "create_response",
         SpanType.ROUTER,
         metadata={"model": request.model, "user": effective_user},
@@ -509,7 +526,7 @@ async def create_response(request: ResponseRequest) -> Response:
 
         return response
 
-    except Exception as e:
+    except Exception:
         end_trace(status="error")
         raise
 
@@ -550,7 +567,7 @@ async def create_response_with_steward(request: ResponseRequest) -> Response:
     user_input = _extract_user_input(request.input)
 
     # Start trace
-    trace = start_trace(
+    start_trace(
         conversation_id=conversation_id,
         user=effective_user,
         request={
@@ -562,7 +579,7 @@ async def create_response_with_steward(request: ResponseRequest) -> Response:
     )
 
     # Start service span
-    service_span = start_span(
+    start_span(
         "create_response_with_steward",
         SpanType.ROUTER,
         metadata={"model": request.model, "user": effective_user},
@@ -706,7 +723,7 @@ async def create_response_with_steward(request: ResponseRequest) -> Response:
 
         return response
 
-    except Exception as e:
+    except Exception:
         end_trace(status="error")
         raise
 

src/responses/streaming.py

@@ -8,14 +8,22 @@ Handles Server-Sent Events (SSE) streaming with proper event types:
 - response.done
 """
 
-from enum import Enum
-from typing import Literal, AsyncGenerator
-import json
 import time
+from collections.abc import AsyncGenerator
+from enum import Enum
+from typing import TYPE_CHECKING, Literal
 
+from src.agents.registry import ModelRegistry
+from src.core.logging_config import get_logger
 from src.core.models import CustomBaseModel
 from src.responses.schemas import Response
-from src.agents.registry import ModelRegistry
+
+if TYPE_CHECKING:
+    from src.agents.steward.schemas import StewardRecommendation
+    from src.core.tool_tracking import ToolCallTracker
+    from src.responses.schemas import ResponseRequest
+
+logger = get_logger(__name__)
 
 
 # ============================================================================
@@ -131,18 +139,17 @@ class StreamingCoordinator:
         Yields:
             StreamEvent: Stream of SSE events
         """
-        from src.responses.service import (
-            _calculate_usage,
-            generate_id,
-            _conversation_history,
-            _direct_delegation_with_results,
-        )
+        import asyncio
+
+        from src.agents.tatlock import TatlockAgent
         from src.core.preprocessing import preprocess_request
         from src.core.tool_tracking import ToolCallTracker
-        from src.responses.schemas import MessageOutputItem, ReasoningOutputItem, OutputTextContent
-        from src.agents.tatlock import TatlockAgent
-        from src.agents.delegation import get_think_message, STREAMING_DELEGATION_WRAPPERS
-        import asyncio
+        from src.responses.schemas import MessageOutputItem, OutputTextContent
+        from src.responses.service import (
+            _calculate_usage,
+            _conversation_history,
+            generate_id,
+        )
 
         output_items = []
 
@@ -280,13 +287,14 @@ class StreamingCoordinator:
         Returns:
             dict: Orchestration results with think_messages list
         """
+        import time as time_module
+
         from src.agents.delegation import (
-            get_think_message,
-            delegate_to_librarian,
             delegate_to_biographer,
             delegate_to_housekeeper,
+            delegate_to_librarian,
+            get_think_message,
         )
-        import time as time_module
 
         expert_results = {}
         tools_called = []
@@ -319,15 +327,26 @@ class StreamingCoordinator:
                     success_msg = get_think_message(agent, user_message, "success")
                     think_messages.append(success_msg + "\n")
                 else:
-                    error_msg = result.error if result else "Unknown error"
-                    expert_results[agent] = f"Error: {error_msg}"
-                    # Emit error think message
+                    # Failed delegations carry a curated user-safe sentence
+                    # in output; exception detail is already in the logs.
                     error_think = get_think_message(agent, user_message, "error")
+                    if result and result.output:
+                        expert_results[agent] = result.output
+                    else:
+                        expert_results[agent] = error_think
+                    # Emit error think message
                     think_messages.append(error_think + "\n")
 
             except Exception as e:
-                expert_results[agent] = f"Error: {e}"
+                logger.error(
+                    "direct_delegation_stream_error",
+                    agent=agent,
+                    error=str(e),
+                    conversation_id=conversation_id,
+                    exc_info=True,
+                )
                 error_think = get_think_message(agent, user_message, "error")
+                expert_results[agent] = error_think
                 think_messages.append(error_think + "\n")
 
         return {
@@ -361,9 +380,10 @@ class StreamingCoordinator:
             event: response.done
             data: {"response": {...}}
         """
-        from src.responses.service import _calculate_usage, generate_id
         import asyncio
 
+        from src.responses.service import _calculate_usage, generate_id
+
         output_items = []
         last_message_text = ""  # Track last streamed message text to compute deltas
 
@@ -488,10 +508,10 @@ class StreamingCoordinator:
     def _convert_output_items(self, items: list) -> list:
         """Convert agent OutputItem objects to schema OutputItem objects."""
         from src.responses.schemas import (
-            MessageOutputItem,
-            ReasoningOutputItem,
             FunctionCallOutputItem,
+            MessageOutputItem,
             OutputTextContent,
+            ReasoningOutputItem,
         )
 
         converted = []
@@ -521,9 +541,9 @@ class StreamingCoordinator:
     def _create_error_event(self, error: Exception) -> ErrorEvent:
         """Create error event from exception."""
         from src.core.exceptions import (
-            RateLimitError,
-            ContextLengthError,
             AppException,
+            ContextLengthError,
+            RateLimitError,
         )
 
         if isinstance(error, RateLimitError):

tests/agents/librarian/test_agent_failures.py

@@ -0,0 +1,60 @@
+"""
+Tests for structured failure behavior of The Librarian entry points.
+
+run_librarian and run_librarian_stream must raise AgentError on failure
+instead of returning/yielding error text as if it were research output,
+and the raised error must not leak exception detail (internal URLs etc.).
+"""
+
+from unittest.mock import AsyncMock, MagicMock, patch
+
+import pytest
+
+from src.agents.librarian.agent import run_librarian, run_librarian_stream
+from src.agents.protocol import AgentError
+
+
+@pytest.mark.unit
+class TestRunLibrarianFailures:
+    """run_librarian raises structured errors instead of returning text."""
+
+    @pytest.mark.asyncio
+    async def test_run_librarian_raises_agent_error(self):
+        """Failures raise AgentError rather than returning error prose."""
+        mock_agent = MagicMock()
+        mock_agent.run = AsyncMock(
+            side_effect=RuntimeError("Connection refused to http://internal:8089")
+        )
+
+        with patch(
+            "src.agents.librarian.agent.get_librarian_agent",
+            return_value=mock_agent,
+        ):
+            with pytest.raises(AgentError) as exc_info:
+                await run_librarian(task="Find Docker docs")
+
+        assert exc_info.value.agent_name == "librarian"
+        # Exception detail stays in logs only
+        assert "internal" not in str(exc_info.value)
+        assert "Connection refused" not in str(exc_info.value)
+
+    @pytest.mark.asyncio
+    async def test_run_librarian_stream_raises_agent_error(self):
+        """Streaming failures raise instead of yielding error text."""
+        mock_agent = MagicMock()
+        mock_agent.run_stream = MagicMock(
+            side_effect=RuntimeError("Connection refused to http://internal:8089")
+        )
+
+        with patch(
+            "src.agents.librarian.agent.get_librarian_agent",
+            return_value=mock_agent,
+        ):
+            collected: list[str] = []
+            with pytest.raises(AgentError) as exc_info:
+                async for delta in run_librarian_stream(task="Find Docker docs"):
+                    collected.append(delta)
+
+        assert exc_info.value.agent_name == "librarian"
+        assert collected == [], "no error text may be yielded as output"
+        assert "internal" not in str(exc_info.value)

tests/agents/librarian/test_tools.py

@@ -5,21 +5,20 @@ Tests the tool functions that wrap the Library-Desk API,
 including the new web search and content extraction tools.
 """
 
-import pytest
-from unittest.mock import AsyncMock, MagicMock, patch
+from unittest.mock import AsyncMock, patch
 
+import pytest
+
+from src.agents.librarian.client import (
+    BatchExtractionResponse,
+    ContentExtractionResult,
+    WebSearchResponse,
+    WebSearchResult,
+)
 from src.agents.librarian.tools import (
-    search_web,
     read_url,
     read_urls_batch,
-    hybrid_search,
-    search_wiki,
-)
-from src.agents.librarian.client import (
-    WebSearchResult,
-    WebSearchResponse,
-    ContentExtractionResult,
-    BatchExtractionResponse,
+    search_web,
 )
 
 
@@ -104,8 +103,10 @@ class TestSearchWeb:
 
     @pytest.mark.asyncio
     async def test_search_web_error_handling(self, mock_client):
-        """Test web search error handling."""
-        mock_client.search_web.side_effect = Exception("Connection failed")
+        """Test web search errors return a user-safe message without internals."""
+        mock_client.search_web.side_effect = Exception(
+            "Connection failed to http://internal-host:8089"
+        )
 
         with patch(
             "src.agents.librarian.tools.LibraryDeskClient"
@@ -115,8 +116,10 @@ class TestSearchWeb:
 
             result = await search_web("test query")
 
-            assert "Error" in result
-            assert "Connection failed" in result
+            assert "unable to search the web" in result
+            # Exception detail (internal URLs etc.) must not leak
+            assert "Connection failed" not in result
+            assert "internal-host" not in result
 
     @pytest.mark.asyncio
     async def test_search_web_with_news_type(self, mock_client):
@@ -227,7 +230,7 @@ class TestReadUrl:
             mock_client_class.return_value.__aenter__.return_value = mock_client
             mock_client_class.return_value.__aexit__.return_value = None
 
-            result = await read_url("https://example.com/long", max_length=2000)
+            await read_url("https://example.com/long", max_length=2000)
 
             mock_client.extract_content.assert_called_with(
                 url="https://example.com/long",

tests/agents/test_delegation.py

@@ -4,18 +4,19 @@ Tests for delegation infrastructure.
 Tests the DelegationTask dataclass and delegation wrapper functions
 that implement the agent-as-tool pattern.
 """
+from unittest.mock import AsyncMock, patch
+
 import pytest
-from unittest.mock import AsyncMock, patch, MagicMock
 
 from src.agents.delegation import (
-    ActionType,
-    DelegationTask,
-    DelegationResult,
     HOUSEHOLD_THINK_MESSAGES,
     STREAMING_DELEGATION_WRAPPERS,
+    ActionType,
+    DelegationResult,
+    DelegationTask,
+    _detect_action_type,
     delegate_to_librarian,
     get_think_message,
-    _detect_action_type,
 )
 
 
@@ -170,11 +171,11 @@ class TestDelegateToLibrarian:
 
     @pytest.mark.asyncio
     async def test_delegate_to_librarian_handles_error(self):
-        """Test delegation handles Librarian errors gracefully."""
+        """Test delegation maps Librarian errors to a user-safe result."""
         with patch(
             "src.agents.librarian.agent.run_librarian",
             new_callable=AsyncMock,
-            side_effect=Exception("Connection refused"),
+            side_effect=Exception("Connection refused to http://internal:8089"),
         ):
             result = await delegate_to_librarian(
                 task="Search for information",
@@ -182,8 +183,15 @@ class TestDelegateToLibrarian:
 
             assert isinstance(result, DelegationResult)
             assert result.success is False
-            assert result.output == ""
-            assert result.error == "Connection refused"
+            # Output carries a curated butler-toned sentence
+            assert result.output == get_think_message(
+                "librarian", "Search for information", "error"
+            )
+            # Exception detail stays in logs only - never in the result
+            assert "Connection refused" not in result.output
+            assert result.error is not None
+            assert "Connection refused" not in result.error
+            assert "internal" not in result.error
 
     @pytest.mark.asyncio
     async def test_delegate_to_librarian_preserves_task(self):