diff --git a/routes/chat_helpers.py b/routes/chat_helpers.py
index ddc193f45..8b7ebff5a 100644
--- a/routes/chat_helpers.py
+++ b/routes/chat_helpers.py
@@ -19,6 +19,7 @@ from src.model_context import estimate_tokens, get_context_length
 from src.auth_helpers import (
     RequestCapability,
     effective_user,
+    is_bearer_principal,
     request_capability as build_request_capability,
 )
 from src.tool_approval_scopes import CHAT_SESSION_APPROVAL_CONTEXT_MARKER
@@ -204,6 +205,11 @@ def _allowed_models_from_privileges(privs: dict) -> Optional[frozenset[str]]:
 def _allowed_models_for_request(request) -> Optional[frozenset[str]]:
     """Return the caller's model allowlist, or ``None`` when unrestricted."""
 
+    # ``effective_user`` is an attribution/storage identity for bearers, not a
+    # browser privilege principal. In particular, an admin-owned token must
+    # not inherit the owner's ADMIN_PRIVILEGES map through this lookup.
+    if is_bearer_principal(request):
+        return None
     try:
         user = effective_user(request)
     except Exception:
@@ -226,6 +232,12 @@ def _enforce_chat_privileges(request, sess) -> None:
     (single-user mode). Admins receive ADMIN_PRIVILEGES from get_privileges,
     which means unrestricted allowed_models / zero cap -> no-op for them.
     """
+    # Bearer authority is defined by the token scope at the route boundary.
+    # Do not turn its owner attribution back into a browser privilege lookup;
+    # that would make an admin-owned token inherit the admin model/cap policy.
+    if is_bearer_principal(request):
+        return
+
     try:
         user = effective_user(request)
     except Exception:
@@ -817,11 +829,16 @@ async def build_chat_context(
 
     # Normalize model ID. Prefer cached endpoint models so group chat does not
     # re-hit slow local /models endpoints on every participant turn.
-    norm = _normalize_model_id_from_cache(sess) or normalize_model_id(
-        sess.endpoint_url,
-        sess.model,
-        owner=getattr(sess, "owner", None),
-    )
+    norm = _normalize_model_id_from_cache(sess)
+    # Model normalization falls back to a live /models or /tags request on a
+    # cache miss. A bearer chat request may use the stored model as-is, but it
+    # must not implicitly refresh an endpoint catalogue while building context.
+    if norm is None and capability.allow_live_probes:
+        norm = normalize_model_id(
+            sess.endpoint_url,
+            sess.model,
+            owner=getattr(sess, "owner", None),
+        )
     if norm:
         sess.model = norm
 
@@ -860,11 +877,22 @@ async def build_chat_context(
     # session history before we know which route can answer and would make a
     # later larger-context candidate unable to recover discarded history.
     if defer_context_shaping:
-        context_length = get_context_length(sess.endpoint_url, sess.model)
+        context_kwargs = {}
+        if not capability.allow_live_probes:
+            context_kwargs["allow_live_probes"] = False
+        context_length = get_context_length(sess.endpoint_url, sess.model, **context_kwargs)
         was_compacted = False
     else:
+        compact_kwargs = {"owner": user}
+        if not capability.allow_live_probes:
+            compact_kwargs["allow_live_probes"] = False
         messages, context_length, was_compacted = await maybe_compact(
-            sess, sess.endpoint_url, sess.model, messages, sess.headers, owner=user,
+            sess,
+            sess.endpoint_url,
+            sess.model,
+            messages,
+            sess.headers,
+            **compact_kwargs,
         )
     _before_trim_messages = len(messages)
     _before_trim_tokens = estimate_tokens(messages)
diff --git a/routes/chat_routes.py b/routes/chat_routes.py
index 6a33d00fe..21d3484e6 100644
--- a/routes/chat_routes.py
+++ b/routes/chat_routes.py
@@ -167,6 +167,7 @@ def _chat_candidate_request_factory(
     *,
     session=None,
     owner: Optional[str] = None,
+    allow_live_probes: bool = True,
 ):
     """Shape one route-neutral Chat prompt for each candidate window."""
 
@@ -180,15 +181,20 @@ def _chat_candidate_request_factory(
 
     async def factory(index, candidate_url, candidate_model, candidate_headers):
         compaction_state = {}
+        compact_kwargs = {
+            "owner": owner,
+            "persist": False,
+            "compaction_state": compaction_state,
+        }
+        if not allow_live_probes:
+            compact_kwargs["allow_live_probes"] = False
         candidate_messages, context_length, was_compacted = await maybe_compact(
             session,
             candidate_url,
             candidate_model,
             list(messages),
             candidate_headers,
-            owner=owner,
-            persist=False,
-            compaction_state=compaction_state,
+            **compact_kwargs,
         )
         if not context_length:
             context_length = fallback_context_length
@@ -878,17 +884,23 @@ def setup_chat_routes(
                 selected_context_length,
                 session=sess,
                 owner=owner,
+                allow_live_probes=request_capability.allow_live_probes,
             )
         requested_model = sess.model
+        llm_kwargs = {
+            "fallback_statuses": foreground_policy.eligible_statuses,
+            "candidate_request_factory": candidate_request_factory,
+            "temperature": ctx.preset.temperature,
+            "max_tokens": ctx.preset.max_tokens,
+            "prompt_type": preset_id,
+            "session_id": session,
+        }
+        if not request_capability.allow_live_probes:
+            llm_kwargs["allow_live_probes"] = False
         reply, actual_candidate, actual_model = await llm_call_async_with_route_fallback(
             foreground_candidates,
             request_messages,
-            fallback_statuses=foreground_policy.eligible_statuses,
-            candidate_request_factory=candidate_request_factory,
-            temperature=ctx.preset.temperature,
-            max_tokens=ctx.preset.max_tokens,
-            prompt_type=preset_id,
-            session_id=session,
+            **llm_kwargs,
         )
         actual_index = _candidate_index(foreground_candidates, actual_candidate)
         apply_compaction_state(
@@ -1605,7 +1617,12 @@ def setup_chat_routes(
         # Enforce per-user privileges
         _privs = {}
         _user = ctx.user
-        if _user and hasattr(request.app.state, 'auth_manager') and request.app.state.auth_manager:
+        if (
+            not api_token_request
+            and _user
+            and hasattr(request.app.state, 'auth_manager')
+            and request.app.state.auth_manager
+        ):
             _privs = request.app.state.auth_manager.get_privileges(_user)
         if _privs:
             if not _privs.get("can_use_bash", True):
@@ -1897,6 +1914,7 @@ def setup_chat_routes(
                     _selected_context_length,
                     session=sess,
                     owner=_user,
+                    allow_live_probes=request_capability.allow_live_probes,
                 )
 
             # Send model name early so the frontend can show it during streaming
@@ -2030,23 +2048,28 @@ def setup_chat_routes(
 
                 # ── Chat mode: call stream_llm directly, NO tools, NO document access ──
                 try:
-                    async for chunk in stream_llm_with_fallback(
-                        _foreground_candidates,
-                        messages,
-                        temperature=ctx.preset.temperature,
+                    stream_kwargs = {
+                        "temperature": ctx.preset.temperature,
                         # Respect the preset; 0/unset = let the server decide (no
                         # cap), matching agent mode. The old hard 4096 fallback
                         # truncated reasoning models mid-<think> — they'd burn the
                         # whole budget thinking and never emit the answer (seen in
                         # Compare on heavy generation prompts).
-                        max_tokens=ctx.preset.max_tokens,
-                        prompt_type=preset_id,
-                        tools=None,
-                        session_id=session,
-                        fallback_statuses=_foreground_policy.eligible_statuses,
-                        fallback_on_empty=_foreground_policy.fallback_on_empty,
-                        candidate_request_factory=_chat_request_factory,
-                        candidate_route_descriptors=_foreground_route_descriptors,
+                        "max_tokens": ctx.preset.max_tokens,
+                        "prompt_type": preset_id,
+                        "tools": None,
+                        "session_id": session,
+                        "fallback_statuses": _foreground_policy.eligible_statuses,
+                        "fallback_on_empty": _foreground_policy.fallback_on_empty,
+                        "candidate_request_factory": _chat_request_factory,
+                        "candidate_route_descriptors": _foreground_route_descriptors,
+                    }
+                    if not request_capability.allow_live_probes:
+                        stream_kwargs["allow_live_probes"] = False
+                    async for chunk in stream_llm_with_fallback(
+                        _foreground_candidates,
+                        messages,
+                        **stream_kwargs,
                     ):
                         if chunk.startswith("data: ") and not chunk.startswith("data: [DONE]"):
                             try:
diff --git a/routes/email_helpers.py b/routes/email_helpers.py
index 257f5f921..67972ef8a 100644
--- a/routes/email_helpers.py
+++ b/routes/email_helpers.py
@@ -34,7 +34,7 @@ from fastapi import Query, HTTPException, Request
 from pydantic import BaseModel
 from typing import Optional, List
 
-from src.auth_helpers import _auth_disabled, get_current_user
+from src.auth_helpers import _auth_disabled, get_current_user, is_bearer_principal
 from src.secret_storage import decrypt as _decrypt
 
 logger = logging.getLogger(__name__)
@@ -420,6 +420,15 @@ def _require_auth(request: Request) -> str:
     unconfigured mode are only honoured if they're coming from
     localhost; everyone else gets 401.
     """
+    # The legacy email router uses one generic dependency for mailbox reads,
+    # drafts, AI helpers, and SMTP send. It has no per-route token-scope
+    # contract, so a bearer must not be allowed to enter it as the ``api``
+    # pseudo-user. Otherwise owner-scoped lookup can miss the token owner and
+    # fall through to process-wide legacy settings credentials below.
+    # Scope-aware integrations must use their dedicated route boundary.
+    if is_bearer_principal(request):
+        raise HTTPException(403, "API tokens must use a scope-aware email route")
+
     u = get_current_user(request)
     if u:
         return u
diff --git a/routes/history/history_routes.py b/routes/history/history_routes.py
index f43123c58..05337c00f 100644
--- a/routes/history/history_routes.py
+++ b/routes/history/history_routes.py
@@ -10,8 +10,11 @@ from fastapi import APIRouter, Depends, Request, HTTPException
 
 from core.models import ChatMessage
 from core.database import SessionLocal, ChatMessage as DbChatMessage, Session as DbSession
-from src.auth_helpers import effective_user, require_chat_scope
-from src.message_metadata import sanitize_client_message_metadata
+from src.auth_helpers import effective_user, is_bearer_principal, require_chat_scope
+from src.message_metadata import (
+    sanitize_client_message_metadata,
+    sanitize_projected_message_metadata,
+)
 from src.topic_analyzer import analyze_topics
 from src.upload_handler import reserve_message_upload_references
 from routes.session_routes import (
@@ -142,11 +145,19 @@ def setup_history_routes(session_manager, upload_handler=None) -> APIRouter:
                 f"Referenced upload is no longer available: {missing_id}",
             )
 
-    def _db_history_entry(m: DbChatMessage) -> Dict[str, Any]:
+    def _display_metadata(value: Any, *, sanitize: bool) -> dict:
+        meta = _metadata_dict(value)
+        if sanitize:
+            return sanitize_projected_message_metadata(meta) or {}
+        return dict(meta)
+
+    def _db_history_entry(
+        m: DbChatMessage,
+        *,
+        sanitize: bool = False,
+    ) -> Dict[str, Any]:
         entry = {"role": m.role, "content": _history_display_content(m.content)}
-        meta = _metadata_dict(m.meta_data)
-        if meta:
-            meta = dict(meta)
+        meta = _display_metadata(m.meta_data, sanitize=sanitize)
         if m.timestamp and "timestamp" not in meta:
             meta["timestamp"] = m.timestamp.isoformat() + "Z"
         if meta:
@@ -161,6 +172,7 @@ def setup_history_routes(session_manager, upload_handler=None) -> APIRouter:
         offset: Optional[int] = None,
     ) -> Dict[str, Any]:
         require_chat_scope(request)
+        sanitize_history = is_bearer_principal(request)
         _verify_session_owner(request, session_id)
         if limit is not None:
             page_limit = max(1, min(int(limit), 100))
@@ -188,7 +200,11 @@ def setup_history_routes(session_manager, upload_handler=None) -> APIRouter:
                     .all()
                 )
                 history_dict = [
-                    entry for entry in (_db_history_entry(m) for m in rows)
+                    entry
+                    for entry in (
+                        _db_history_entry(m, sanitize=sanitize_history)
+                        for m in rows
+                    )
                     if not (entry.get("metadata") or {}).get("hidden")
                 ]
                 return {
@@ -214,7 +230,10 @@ def setup_history_routes(session_manager, upload_handler=None) -> APIRouter:
         for msg in session.history:
             if isinstance(msg, ChatMessage):
                 # Skip hidden messages (e.g. compaction summaries for AI context)
-                msg_meta = _metadata_dict(msg.metadata)
+                msg_meta = _display_metadata(
+                    msg.metadata,
+                    sanitize=sanitize_history,
+                )
                 if msg_meta.get("hidden"):
                     continue
                 entry = {"role": msg.role, "content": _history_display_content(msg.content)}
@@ -222,7 +241,10 @@ def setup_history_routes(session_manager, upload_handler=None) -> APIRouter:
                     entry["metadata"] = msg_meta
                 history_dict.append(entry)
             elif isinstance(msg, dict):
-                msg_meta = _metadata_dict(msg.get("metadata"))
+                msg_meta = _display_metadata(
+                    msg.get("metadata"),
+                    sanitize=sanitize_history,
+                )
                 if msg_meta.get("hidden"):
                     continue
                 entry = {
@@ -248,7 +270,11 @@ def setup_history_routes(session_manager, upload_handler=None) -> APIRouter:
                 )
                 # Response excludes hidden messages, matching the in-memory path.
                 history_dict = [
-                    entry for entry in (_db_history_entry(m) for m in db_messages)
+                    entry
+                    for entry in (
+                        _db_history_entry(m, sanitize=sanitize_history)
+                        for m in db_messages
+                    )
                     if not (entry.get("metadata") or {}).get("hidden")
                 ]
             except Exception as e:
@@ -653,12 +679,15 @@ def setup_history_routes(session_manager, upload_handler=None) -> APIRouter:
                 # in-memory messages, corrupting their _db_id and breaking
                 # edit/delete-by-id on the original conversation.
                 meta = dict(msg.metadata) if isinstance(msg.metadata, dict) else None
+                if is_bearer_principal(request):
+                    meta = sanitize_projected_message_metadata(meta)
                 new_session.add_message(ChatMessage(msg.role, msg.content, meta))
-            try:
-                from src.event_bus import fire_event
-                fire_event("session_created", getattr(source, 'owner', None))
-            except Exception:
-                logger.debug("session_created event dispatch failed", exc_info=True)
+            if not is_bearer_principal(request):
+                try:
+                    from src.event_bus import fire_event
+                    fire_event("session_created", getattr(source, 'owner', None))
+                except Exception:
+                    logger.debug("session_created event dispatch failed", exc_info=True)
 
             return {
                 "status": "ok",
diff --git a/routes/session_routes.py b/routes/session_routes.py
index f7447547c..8428469e3 100644
--- a/routes/session_routes.py
+++ b/routes/session_routes.py
@@ -11,7 +11,13 @@ from core.session_manager import SessionManager
 from core.models import ChatMessage
 from src.request_models import SessionResponse
 from core.database import Session as DbSession, SessionLocal, Document, GalleryImage, utcnow_naive
-from src.auth_helpers import effective_user, _auth_disabled, owner_filter, require_chat_scope
+from src.auth_helpers import (
+    effective_user,
+    _auth_disabled,
+    is_bearer_principal,
+    owner_filter,
+    require_chat_scope,
+)
 from src.message_metadata import sanitize_client_message_metadata
 from src.session_image_cleanup import _generated_image_path_for_cleanup, session_image_refs
 from src.session_actions import is_session_recently_active
@@ -158,7 +164,10 @@ def _reject_raw_endpoint_url_for_non_admin(
     # Raw URLs make the server dial whatever host the request supplies. For
     # non-admin users, require a saved endpoint row so normal owner scoping and
     # endpoint validation have already happened.
-    if user and not _current_user_is_admin(request, user):
+    # A bearer may be attributed to an admin owner for storage and endpoint
+    # visibility, but it is still not an interactive admin principal. Raw
+    # endpoint URLs therefore remain unavailable to every bearer request.
+    if is_bearer_principal(request) or (user and not _current_user_is_admin(request, user)):
         raise HTTPException(403, "Choose a registered model endpoint")
 
 
@@ -450,14 +459,17 @@ def setup_session_routes(
             from src.endpoint_resolver import build_headers
             session.headers = build_headers(resolved_key, resolved_base)
             _persist_session_headers(sid, session.headers)
-        # Fire webhook (sync-safe)
-        if webhook_manager:
-            webhook_manager.fire_and_forget("session.created", {
-                "session_id": sid, "name": session.name, "model": model_to_use,
-            })
-        # Fire event for automation tasks
-        from src.event_bus import fire_event
-        fire_event("session_created", user)
+        # A bearer can create owner-attributed chat data, but must not cause
+        # owner lifecycle automation or webhook delivery as a side effect.
+        if not is_bearer_principal(request):
+            # Fire webhook (sync-safe)
+            if webhook_manager:
+                webhook_manager.fire_and_forget("session.created", {
+                    "session_id": sid, "name": session.name, "model": model_to_use,
+                })
+            # Fire event for automation tasks
+            from src.event_bus import fire_event
+            fire_event("session_created", user)
         return SessionResponse(
             id=sid,
             name=session.name,
@@ -943,8 +955,9 @@ def setup_session_routes(
         )
         session.headers = {"Authorization": f"Bearer {OPENAI_API_KEY}"}
         session_manager.save_sessions()
-        from src.event_bus import fire_event
-        fire_event("session_created", user)
+        if not is_bearer_principal(request):
+            from src.event_bus import fire_event
+            fire_event("session_created", user)
         return {"id": sid, "name": "", "model": model}
     
     @router.post("/session/{session_id}/important")
diff --git a/routes/upload_routes.py b/routes/upload_routes.py
index 8d6e1514d..47e83ac17 100644
--- a/routes/upload_routes.py
+++ b/routes/upload_routes.py
@@ -21,7 +21,7 @@ from core.database import (
     Note,
     Session as DbSession,
 )
-from src.auth_helpers import effective_user, require_chat_scope
+from src.auth_helpers import effective_user, require_chat_scope, require_non_bearer_request
 from src.attachment_refs import attachment_refs_from_metadata
 from src.constants import GENERATED_IMAGES_DIR
 from src.upload_handler import (
@@ -462,6 +462,7 @@ def setup_upload_routes(upload_handler):
         Cached under UPLOAD_DIR/.vision/{file_id}.txt — first call computes,
         subsequent loads are instant. Pass force=1 to recompute."""
         require_chat_scope(request)
+        require_non_bearer_request(request)
         if not upload_handler.validate_upload_id(file_id):
             raise HTTPException(400, "Invalid file ID")
         info = _load_upload_info(file_id)
@@ -507,6 +508,7 @@ def setup_upload_routes(upload_handler):
         """Persist a user-edited vision/OCR text for an attachment. Stored in
         the same cache file so the chat send picks it up as the override."""
         require_chat_scope(request)
+        require_non_bearer_request(request)
         if not upload_handler.validate_upload_id(file_id):
             raise HTTPException(400, "Invalid file ID")
         info = _load_upload_info(file_id)
diff --git a/routes/webhook/webhook_routes.py b/routes/webhook/webhook_routes.py
index 066e26189..87f7f1440 100644
--- a/routes/webhook/webhook_routes.py
+++ b/routes/webhook/webhook_routes.py
@@ -9,7 +9,7 @@ from fastapi import APIRouter, HTTPException, Request, Form
 from pydantic import BaseModel, Field
 
 from core.database import SessionLocal, Webhook, ModelEndpoint
-from src.auth_helpers import owner_filter, require_chat_scope
+from src.auth_helpers import is_bearer_principal, owner_filter, require_chat_scope
 from src.url_security import validate_public_http_url
 from src.webhook_manager import WebhookManager, validate_webhook_url, validate_events
 
@@ -385,10 +385,14 @@ def setup_webhook_routes(
         sess.add_message(ChatMessage("assistant", reply))
         session_manager.save_sessions()
 
-        webhook_manager.fire_and_forget("chat.completed", {
-            "session_id": session_id, "model": sess.model,
-            "user_message": message[:2000], "response": reply[:2000],
-        })
+        # /api/v1/chat remains a synchronous bearer integration: the response
+        # is returned normally, but the token must not fan that content out to
+        # an owner-configured asynchronous callback after authorization ends.
+        if not is_bearer_principal(request):
+            webhook_manager.fire_and_forget("chat.completed", {
+                "session_id": session_id, "model": sess.model,
+                "user_message": message[:2000], "response": reply[:2000],
+            })
 
         return {"response": reply, "session_id": session_id, "model": sess.model}
 
diff --git a/src/auth_helpers.py b/src/auth_helpers.py
index 752355c2b..ae7a1b232 100644
--- a/src/auth_helpers.py
+++ b/src/auth_helpers.py
@@ -31,6 +31,7 @@ class RequestCapability:
     allow_detached_execution: bool
     allow_message_events: bool
     allow_auto_naming: bool
+    allow_live_probes: bool
 
 
 def is_bearer_principal(request: Request) -> bool:
@@ -101,6 +102,7 @@ def request_capability(request: Request) -> RequestCapability:
         allow_detached_execution=not bearer,
         allow_message_events=not bearer,
         allow_auto_naming=not bearer,
+        allow_live_probes=not bearer,
     )
 
 
diff --git a/src/context_compactor.py b/src/context_compactor.py
index d6adf5bb4..94e4b7638 100644
--- a/src/context_compactor.py
+++ b/src/context_compactor.py
@@ -330,12 +330,16 @@ async def maybe_compact(
     *,
     persist: bool = True,
     compaction_state: Optional[Dict[str, Any]] = None,
+    allow_live_probes: bool = True,
 ) -> tuple:
     """Check context usage and compact if above threshold.
 
     Returns (messages, context_length, was_compacted).
     """
-    context_length = get_context_length(endpoint_url, model)
+    context_kwargs = {}
+    if not allow_live_probes:
+        context_kwargs["allow_live_probes"] = False
+    context_length = get_context_length(endpoint_url, model, **context_kwargs)
     used = estimate_tokens(messages)
     pct = (used / context_length) * 100 if context_length else 0
 
@@ -392,6 +396,9 @@ async def maybe_compact(
     ]
 
     try:
+        summary_kwargs = {}
+        if not allow_live_probes:
+            summary_kwargs["allow_live_probes"] = False
         summary = await llm_call_async(
             compact_url,
             compact_model,
@@ -400,6 +407,7 @@ async def maybe_compact(
             max_tokens=SUMMARY_MAX_TOKENS,
             headers=compact_headers,
             timeout=30,
+            **summary_kwargs,
         )
     except Exception as e:
         logger.error(f"Compaction summary failed: {e}")
diff --git a/src/llm_core.py b/src/llm_core.py
index cea829d45..699460e00 100644
--- a/src/llm_core.py
+++ b/src/llm_core.py
@@ -1903,6 +1903,7 @@ def list_model_ids(
     *,
     owner: Optional[str] = None,
     endpoint_id: Optional[str] = None,
+    allow_live_probes: bool = True,
 ) -> List[str]:
     """List available model IDs from an endpoint."""
     cached = _configured_cached_model_ids(base_chat_url, owner=owner, endpoint_id=endpoint_id)
@@ -1911,6 +1912,8 @@ def list_model_ids(
     provider = _detect_provider(base_chat_url)
     if provider == "anthropic":
         return list(ANTHROPIC_MODELS)
+    if not allow_live_probes:
+        return []
     try:
         h = {}
         if headers:
@@ -1952,9 +1955,16 @@ def normalize_model_id(
     *,
     owner: Optional[str] = None,
     endpoint_id: Optional[str] = None,
+    allow_live_probes: bool = True,
 ) -> Optional[str]:
     """Normalize a model ID to match available models."""
-    avail = list_model_ids(endpoint_url, timeout, owner=owner, endpoint_id=endpoint_id)
+    avail = list_model_ids(
+        endpoint_url,
+        timeout,
+        owner=owner,
+        endpoint_id=endpoint_id,
+        allow_live_probes=allow_live_probes,
+    )
     if not avail:
         return None
     if requested in avail:
@@ -1968,7 +1978,8 @@ def normalize_model_id(
 
 def llm_call(url: str, model: str, messages: List[Dict], temperature: float = LLMConfig.DEFAULT_TEMPERATURE,
              max_tokens: int = LLMConfig.DEFAULT_MAX_TOKENS, headers: Optional[Dict] = None,
-             timeout: int = LLMConfig.DEFAULT_TIMEOUT, prompt_type: Optional[str] = None) -> str:
+             timeout: int = LLMConfig.DEFAULT_TIMEOUT, prompt_type: Optional[str] = None,
+             allow_live_probes: bool = True) -> str:
     """Synchronous LLM call with optional prompt type enhancement."""
     h = _provider_headers(_detect_provider(url))
     # Tolerate headers that arrive as a JSON string (some sessions stored them
@@ -2012,9 +2023,12 @@ def llm_call(url: str, model: str, messages: List[Dict], temperature: float = LL
         payload = _build_anthropic_payload(model, messages_copy, temperature, max_tokens)
     elif provider == "ollama":
         target_url = _normalize_ollama_url(url)
+        context_kwargs = {}
+        if not allow_live_probes:
+            context_kwargs["allow_live_probes"] = False
         payload = _build_ollama_payload(
             model, messages_copy, temperature, max_tokens,
-            stream=False, num_ctx=get_context_length(url, model),
+            stream=False, num_ctx=get_context_length(url, model, **context_kwargs),
         )
     else:
         target_url = _normalize_openai_chat_url(url)
@@ -2273,6 +2287,7 @@ async def llm_call_async(
     workload: str = "foreground",
     availability_only_transport: bool = False,
     return_model_metadata: bool = False,
+    allow_live_probes: bool = True,
 ) -> str | tuple[str, str]:
     """Asynchronous LLM call using httpx with connection pooling, timeout, retry logic, and performance logging."""
     provider = _detect_provider(url)
@@ -2307,6 +2322,9 @@ async def llm_call_async(
         # Reuse stream_llm's validated Codex SSE path and collect deltas.
         parts: List[str] = []
         actual_model = model
+        stream_kwargs = {"workload": workload}
+        if not allow_live_probes:
+            stream_kwargs["allow_live_probes"] = False
         async for chunk in stream_llm(
             url,
             model,
@@ -2315,7 +2333,7 @@ async def llm_call_async(
             max_tokens=max_tokens,
             headers=headers,
             timeout=timeout,
-            workload=workload,
+            **stream_kwargs,
         ):
             event_is_error = False
             for line in str(chunk).splitlines():
@@ -2372,9 +2390,12 @@ async def llm_call_async(
         h = {"Content-Type": "application/json"}
         if headers:
             h.update(headers)
+        context_kwargs = {}
+        if not allow_live_probes:
+            context_kwargs["allow_live_probes"] = False
         payload = _build_ollama_payload(
             model, messages_copy, temperature, max_tokens,
-            stream=False, num_ctx=get_context_length(url, model),
+            stream=False, num_ctx=get_context_length(url, model, **context_kwargs),
         )
     else:
         target_url = _normalize_openai_chat_url(url)
@@ -2560,9 +2581,13 @@ async def stream_llm(url: str, model: str, messages: List[Dict], temperature: fl
                      max_tokens: int = LLMConfig.DEFAULT_MAX_TOKENS, headers: Optional[Dict] = None,
                      timeout: int = LLMConfig.STREAM_TIMEOUT, prompt_type: Optional[str] = None,
                      tools: Optional[List[Dict]] = None, session_id: Optional[str] = None,
-                     tool_choice_none: bool = False, workload: str = "foreground"):
+                     tool_choice_none: bool = False, workload: str = "foreground",
+                     allow_live_probes: bool = True):
     target_url = _stream_target_url(url)
     async with _local_model_slot(target_url, model, workload):
+        inner_kwargs = {}
+        if not allow_live_probes:
+            inner_kwargs["allow_live_probes"] = False
         async for chunk in _stream_llm_inner(
             url,
             model,
@@ -2575,6 +2600,7 @@ async def stream_llm(url: str, model: str, messages: List[Dict], temperature: fl
             tools=tools,
             session_id=session_id,
             tool_choice_none=tool_choice_none,
+            **inner_kwargs,
         ):
             yield chunk
 
@@ -2583,7 +2609,7 @@ async def _stream_llm_inner(url: str, model: str, messages: List[Dict], temperat
                             max_tokens: int = LLMConfig.DEFAULT_MAX_TOKENS, headers: Optional[Dict] = None,
                             timeout: int = LLMConfig.STREAM_TIMEOUT, prompt_type: Optional[str] = None,
                             tools: Optional[List[Dict]] = None, session_id: Optional[str] = None,
-                            tool_choice_none: bool = False):
+                            tool_choice_none: bool = False, allow_live_probes: bool = True):
     """Stream LLM responses with improved error handling.
 
     Yields SSE chunks:
@@ -2618,9 +2644,14 @@ async def _stream_llm_inner(url: str, model: str, messages: List[Dict], temperat
         h = {"Content-Type": "application/json"}
         if headers:
             h.update(headers)
+        context_kwargs = {}
+        if not allow_live_probes:
+            context_kwargs["allow_live_probes"] = False
         payload = _build_ollama_payload(
             model, messages_copy, temperature, max_tokens,
-            stream=True, tools=tools, num_ctx=get_context_length(url, model),
+            stream=True,
+            tools=tools,
+            num_ctx=get_context_length(url, model, **context_kwargs),
         )
     elif provider == "chatgpt-subscription":
         target_url = _normalize_chatgpt_subscription_url(url)
diff --git a/src/model_context.py b/src/model_context.py
index b6afa801e..8c4c0e416 100644
--- a/src/model_context.py
+++ b/src/model_context.py
@@ -238,16 +238,31 @@ KNOWN_CONTEXT_WINDOWS = {
 _context_cache: Dict[Tuple[str, str], Tuple[int, bool]] = {}
 
 
-def _get_context_length_cached(endpoint_url: str, model: str) -> Tuple[int, bool]:
+def _get_context_length_cached(
+    endpoint_url: str,
+    model: str,
+    *,
+    allow_live_probes: bool = True,
+) -> Tuple[int, bool]:
     """Return (context_length, known). ``known`` is False only when the value is a
     bare DEFAULT_CONTEXT fallback (no endpoint report and not in the known table)."""
+    cache_key = (endpoint_url, model)
+    if not allow_live_probes:
+        # A bearer may consume metadata already learned by an interactive or
+        # explicitly privileged refresh, but a context build must not cause a
+        # new /slots, /models, or catalog request or populate those caches.
+        cached = _context_cache.get(cache_key)
+        if cached:
+            return cached
+        known = _lookup_known(model)
+        return (known, True) if known else (DEFAULT_CONTEXT, False)
+
     configured_kind = _configured_endpoint_kind(endpoint_url)
     is_local = is_local_endpoint(endpoint_url)
     # Key on (endpoint_url, model): the same model id can be served by two
     # different remote endpoints with different real context windows (e.g. a
     # capped proxy vs. the full provider), so caching by model id alone would
     # serve one endpoint's window for the other (issue #2603).
-    cache_key = (endpoint_url, model)
     if not is_local and cache_key in _context_cache:
         return _context_cache[cache_key]
 
@@ -261,23 +276,41 @@ def _get_context_length_cached(endpoint_url: str, model: str) -> Tuple[int, bool
     return ctx, known
 
 
-def get_context_length(endpoint_url: str, model: str) -> int:
+def get_context_length(
+    endpoint_url: str,
+    model: str,
+    *,
+    allow_live_probes: bool = True,
+) -> int:
     """Get the context window size for a model.
 
     Queries /v1/models on the endpoint and looks for context_length
     or context_window fields. Caches result per (endpoint, model).
     Falls back to DEFAULT_CONTEXT if unavailable.
     """
-    return _get_context_length_cached(endpoint_url, model)[0]
+    return _get_context_length_cached(
+        endpoint_url,
+        model,
+        allow_live_probes=allow_live_probes,
+    )[0]
 
 
-def get_context_length_known(endpoint_url: str, model: str) -> Tuple[int, bool]:
+def get_context_length_known(
+    endpoint_url: str,
+    model: str,
+    *,
+    allow_live_probes: bool = True,
+) -> Tuple[int, bool]:
     """Like ``get_context_length`` but also returns whether the window was actually
     discovered (endpoint-reported or in the known-models table) rather than the bare
     DEFAULT_CONTEXT fallback. Callers that *scale* a budget off the window must not
     trust an unknown value — a fallback 128K isn't proof the model holds 128K
     (review on #4122)."""
-    return _get_context_length_cached(endpoint_url, model)
+    return _get_context_length_cached(
+        endpoint_url,
+        model,
+        allow_live_probes=allow_live_probes,
+    )
 
 
 def budget_context_for_model(endpoint_url: str, model: str, *, fallback: int = 0) -> int:
diff --git a/tests/test_api_token_security_cycle3.py b/tests/test_api_token_security_cycle3.py
new file mode 100644
index 000000000..031982592
--- /dev/null
+++ b/tests/test_api_token_security_cycle3.py
@@ -0,0 +1,558 @@
+"""Cycle-3 regressions for the bearer capability boundary.
+
+The tests intentionally call route endpoints directly as well as exercising
+the shared helpers. FastAPI dependency execution is not a substitute for the
+handler's own authorization checks when an endpoint can be called by another
+in-process route or test harness.
+"""
+
+import json
+from datetime import datetime
+from types import SimpleNamespace
+from unittest.mock import MagicMock
+
+import pytest
+from fastapi import HTTPException
+
+
+def _request(*, bearer=True, owner="alice", scopes=("chat",), current_user="api", auth_manager=None):
+    return SimpleNamespace(
+        state=SimpleNamespace(
+            api_token=bearer,
+            api_token_owner=owner if bearer else None,
+            api_token_scopes=list(scopes),
+            current_user=current_user if bearer else current_user,
+        ),
+        app=SimpleNamespace(state=SimpleNamespace(auth_manager=auth_manager)),
+        headers={},
+    )
+
+
+class _JsonRequest:
+    def __init__(self, body=None, *, bearer=True, owner="alice", scopes=("chat",)):
+        self.state = SimpleNamespace(
+            api_token=bearer,
+            api_token_owner=owner if bearer else None,
+            api_token_scopes=list(scopes),
+            current_user="api" if bearer else owner,
+        )
+        self.app = SimpleNamespace(state=SimpleNamespace(auth_manager=None))
+        self.headers = {}
+        self.body = body or {}
+
+    async def json(self):
+        return self.body
+
+
+def _latest_endpoint(router, path, method):
+    for route in reversed(router.routes):
+        if route.path == path and method in (route.methods or set()):
+            return route.endpoint
+    raise AssertionError(f"route not found: {method} {path}")
+
+
+def test_admin_owned_bearer_does_not_inherit_raw_endpoint_or_model_privileges():
+    from routes.chat_helpers import _allowed_models_for_request, _enforce_chat_privileges
+    from routes.session_routes import _reject_raw_endpoint_url_for_non_admin
+
+    auth_manager = MagicMock()
+    auth_manager.is_admin.return_value = True
+    auth_manager.get_privileges.side_effect = AssertionError("bearer used owner privilege lookup")
+    request = _request(owner="admin", auth_manager=auth_manager)
+
+    with pytest.raises(HTTPException) as exc:
+        _reject_raw_endpoint_url_for_non_admin(
+            request,
+            "admin",
+            endpoint_id="",
+            endpoint_url="http://127.0.0.1:9/private",
+        )
+    assert exc.value.status_code == 403
+    assert _allowed_models_for_request(request) is None
+    _enforce_chat_privileges(request, SimpleNamespace(model="admin-only"))
+    auth_manager.get_privileges.assert_not_called()
+
+    cookie_request = _request(
+        bearer=False,
+        owner=None,
+        current_user="admin",
+        auth_manager=auth_manager,
+    )
+    auth_manager.get_privileges.side_effect = None
+    auth_manager.get_privileges.return_value = {
+        "allowed_models": ["admin-only"],
+        "allowed_models_restricted": True,
+    }
+    _reject_raw_endpoint_url_for_non_admin(
+        cookie_request,
+        "admin",
+        endpoint_id="",
+        endpoint_url="http://127.0.0.1:9/private",
+    )
+    assert _allowed_models_for_request(cookie_request) == frozenset({"admin-only"})
+
+
+class _SessionManager:
+    def __init__(self):
+        self.sessions = {}
+        self.saved = 0
+
+    def create_session(self, **kwargs):
+        session = SimpleNamespace(
+            id=kwargs["session_id"],
+            name=kwargs.get("name", ""),
+            endpoint_url=kwargs.get("endpoint_url", ""),
+            model=kwargs.get("model", ""),
+            rag=kwargs.get("rag", False),
+            owner=kwargs.get("owner"),
+            headers={},
+            history=[],
+        )
+        self.sessions[session.id] = session
+        return session
+
+    def save_sessions(self):
+        self.saved += 1
+
+
+def test_bearer_session_lifecycle_routes_do_not_emit_webhook_or_event(monkeypatch):
+    import src.event_bus as event_bus
+    from routes import session_routes
+
+    events = []
+    monkeypatch.setattr(event_bus, "fire_event", lambda *args, **kwargs: events.append((args, kwargs)))
+    manager = _SessionManager()
+    webhook_manager = MagicMock()
+    router = session_routes.setup_session_routes(
+        manager,
+        {
+            "REQUEST_TIMEOUT": 1,
+            "OPENAI_API_KEY": "server-key",
+            "SESSIONS_FILE": "sessions.json",
+        },
+        webhook_manager=webhook_manager,
+    )
+    request = _request()
+
+    create = _latest_endpoint(router, "/api/session", "POST")
+    with pytest.raises(HTTPException) as exc:
+        create(
+            request,
+            name="Private endpoint",
+            endpoint_url="http://127.0.0.1:9/private",
+            model="stored-model",
+            rag="false",
+            skip_validation="true",
+            api_key="",
+            endpoint_id="",
+        )
+    assert exc.value.status_code == 403
+    assert manager.sessions == {}
+
+    result = create(
+        request,
+        name="API chat",
+        endpoint_url="",
+        model="stored-model",
+        rag="false",
+        skip_validation="true",
+        api_key="",
+        endpoint_id="",
+    )
+    assert result.model == "stored-model"
+
+    create_openai = _latest_endpoint(router, "/api/session/openai", "POST")
+    openai_result = create_openai(request, name="OpenAI", model="gpt-4o", rag="false")
+    assert openai_result["model"] == "gpt-4o"
+    webhook_manager.fire_and_forget.assert_not_called()
+    assert events == []
+
+    cookie_request = _request(bearer=False, owner=None, current_user="alice", scopes=())
+    cookie_result = create(
+        cookie_request,
+        name="Browser chat",
+        endpoint_url="",
+        model="stored-model",
+        rag="false",
+        skip_validation="true",
+        api_key="",
+        endpoint_id="",
+    )
+    assert cookie_result.model == "stored-model"
+    assert events and events[-1][0] == ("session_created", "alice")
+
+
+def test_generic_email_dependency_rejects_bearer_before_legacy_fallback(monkeypatch):
+    from routes import email_helpers
+
+    with pytest.raises(HTTPException) as exc:
+        email_helpers._require_auth(_request(owner="alice", scopes=("chat",)))
+    assert exc.value.status_code == 403
+
+    assert email_helpers._require_auth(
+        _request(bearer=False, owner=None, current_user="alice", scopes=())
+    ) == "alice"
+    monkeypatch.setattr(email_helpers, "_auth_disabled", lambda: True)
+    assert email_helpers._require_auth(
+        _request(bearer=False, owner=None, current_user=None, scopes=())
+    ) == ""
+
+
+@pytest.mark.asyncio
+async def test_bearer_context_builder_uses_no_live_model_or_context_probes(monkeypatch):
+    from routes import chat_helpers
+    from src.auth_helpers import request_capability
+
+    calls = {"normalize": 0, "compact": []}
+
+    class _ChatHandler:
+        def validate_and_extract_preset(self, _preset_id):
+            return 0.2, 64, None, None
+
+        async def preprocess_message(self, message, att_ids, sess, **kwargs):
+            assert kwargs["allow_tool_preprocessing"] is False
+            return message, message, message, [], []
+
+    class _ChatProcessor:
+        def build_context_preface(self, **kwargs):
+            return [], [], []
+
+    def fail_normalize(*args, **kwargs):
+        calls["normalize"] += 1
+        raise AssertionError("bearer context performed a live model probe")
+
+    async def fake_compact(*args, **kwargs):
+        calls["compact"].append(kwargs)
+        return args[3], 128000, False
+
+    monkeypatch.setattr(chat_helpers, "_normalize_model_id_from_cache", lambda _sess: None)
+    monkeypatch.setattr(chat_helpers, "normalize_model_id", fail_normalize)
+    monkeypatch.setattr(chat_helpers, "maybe_compact", fake_compact)
+    monkeypatch.setattr(chat_helpers, "load_prefs_for_user", lambda _owner: {})
+
+    session = SimpleNamespace(
+        endpoint_url="http://127.0.0.1:9999/v1/chat/completions",
+        model="uncached-model",
+        headers={},
+        owner="alice",
+        history=[],
+        get_context_messages=lambda: [],
+        add_message=lambda _message: None,
+    )
+    request = _request()
+    context = await chat_helpers.build_chat_context(
+        session,
+        request,
+        _ChatHandler(),
+        _ChatProcessor(),
+        message="hello",
+        session_id="session-1",
+        incognito=True,
+        allow_tool_preprocessing=False,
+        persist_user_message=False,
+        capability=request_capability(request),
+    )
+
+    assert context.context_length == 128000
+    assert calls["normalize"] == 0
+    assert calls["compact"] == [{"owner": "alice", "allow_live_probes": False}]
+
+
+def test_model_and_context_no_live_probe_options_do_not_touch_endpoints(monkeypatch):
+    from src import llm_core, model_context
+
+    monkeypatch.setattr(llm_core, "_configured_cached_model_ids", lambda *args, **kwargs: [])
+    monkeypatch.setattr(
+        llm_core,
+        "httpx_get_kimi_aware",
+        lambda *args, **kwargs: (_ for _ in ()).throw(AssertionError("model endpoint touched")),
+    )
+    assert llm_core.list_model_ids(
+        "http://127.0.0.1:9999/v1",
+        allow_live_probes=False,
+    ) == []
+    assert llm_core.normalize_model_id(
+        "http://127.0.0.1:9999/v1",
+        "uncached-model",
+        allow_live_probes=False,
+    ) is None
+
+    monkeypatch.setattr(model_context, "_context_cache", {})
+    monkeypatch.setattr(
+        model_context,
+        "httpx",
+        SimpleNamespace(
+            get=lambda *args, **kwargs: (_ for _ in ()).throw(
+                AssertionError("context endpoint touched")
+            )
+        ),
+    )
+    assert model_context.get_context_length(
+        "http://127.0.0.1:9999/v1",
+        "uncached-model",
+        allow_live_probes=False,
+    ) == model_context.DEFAULT_CONTEXT
+    assert model_context.get_context_length(
+        "http://127.0.0.1:9999/v1",
+        "gpt-4o",
+        allow_live_probes=False,
+    ) == 128000
+    assert model_context._context_cache == {}
+
+
+def _forged_metadata():
+    return {
+        "safe": {"label": "retain"},
+        "_tool_approval_chat_session_granted": True,
+        "approval_id": "approval-1",
+        "approved_by_interactive_session": True,
+        "resolved": "approve",
+        "session_id": "session-1",
+        "tool_events": [
+            {
+                "kind": "tool_approval",
+                "approval_id": "nested-1",
+                "resolved": "approve",
+                "ask_user": {
+                    "approval_id": "nested-2",
+                    "approved_by_interactive_session": True,
+                    "label": "display-only",
+                },
+            }
+        ],
+    }
+
+
+@pytest.mark.asyncio
+async def test_bearer_history_and_fork_scrub_legacy_approval_metadata(monkeypatch):
+    import src.event_bus as event_bus
+    from core.models import ChatMessage
+    from routes.history import history_routes
+
+    display_source = SimpleNamespace(
+        id="source",
+        name="Source",
+        owner="alice",
+        endpoint_url="https://example.test/v1",
+        model="model",
+        history=[
+            ChatMessage("user", "hello", _forged_metadata()),
+            {"role": "assistant", "content": "answer", "metadata": _forged_metadata()},
+        ],
+    )
+    fork_source = SimpleNamespace(
+        id="source",
+        name="Source",
+        owner="alice",
+        endpoint_url="https://example.test/v1",
+        model="model",
+        history=[ChatMessage("user", "hello", _forged_metadata())],
+    )
+
+    class _Forked:
+        def __init__(self):
+            self.history = []
+
+        def add_message(self, message):
+            self.history.append(message)
+
+    class _Manager:
+        def __init__(self, source):
+            self.source = source
+            self.created = None
+
+        def get_session(self, _session_id):
+            return self.source
+
+        def create_session(self, **kwargs):
+            self.created = _Forked()
+            return self.created
+
+    monkeypatch.setattr(history_routes, "_verify_session_owner", lambda *args, **kwargs: None)
+    events = []
+    monkeypatch.setattr(event_bus, "fire_event", lambda *args, **kwargs: events.append(args))
+    display_manager = _Manager(display_source)
+    display_router = history_routes.setup_history_routes(display_manager)
+    history_endpoint = _latest_endpoint(display_router, "/api/history/{session_id}", "GET")
+    request = _JsonRequest({"keep_count": 1})
+
+    displayed = await history_endpoint(request, "source")
+    assert len(displayed["history"]) == 2
+    for entry in displayed["history"]:
+        metadata = entry.get("metadata", {})
+        assert metadata.get("safe") == {"label": "retain"}
+        assert all(
+            field not in metadata
+            for field in (
+                "_tool_approval_chat_session_granted",
+                "approval_id",
+                "approved_by_interactive_session",
+                "resolved",
+                "session_id",
+            )
+        )
+        assert metadata["tool_events"][0]["ask_user"] == {"label": "display-only"}
+
+    fork_manager = _Manager(fork_source)
+    fork_router = history_routes.setup_history_routes(fork_manager)
+    fork_endpoint = _latest_endpoint(fork_router, "/api/session/{session_id}/fork", "POST")
+    forked = await fork_endpoint(request, "source")
+    assert forked["status"] == "ok"
+    assert events == []
+    assert fork_manager.created.history[0].metadata["safe"] == {"label": "retain"}
+    assert "approval_id" not in fork_manager.created.history[0].metadata
+
+
+class _ColumnQuery:
+    def __init__(self, result, *, count=0, rows=None):
+        self.result = result
+        self.count_value = count
+        self.rows = rows or []
+
+    def filter(self, *args):
+        return self
+
+    def order_by(self, *args):
+        return self
+
+    def offset(self, value):
+        return self
+
+    def limit(self, value):
+        return self
+
+    def first(self):
+        return self.result
+
+    def count(self):
+        return self.count_value
+
+    def all(self):
+        return self.rows
+
+
+class _HistoryDb:
+    def __init__(self, history_routes, session_row, message_rows):
+        self.history_routes = history_routes
+        self.session_row = session_row
+        self.message_rows = message_rows
+
+    def query(self, model):
+        if model is self.history_routes.DbSession:
+            return _ColumnQuery(self.session_row)
+        return _ColumnQuery(None, count=len(self.message_rows), rows=self.message_rows)
+
+    def close(self):
+        return None
+
+
+@pytest.mark.asyncio
+async def test_bearer_paginated_history_scrubs_db_projection(monkeypatch):
+    from routes.history import history_routes
+    db_session = SimpleNamespace(model="model", endpoint_url="https://example.test/v1", name="Chat")
+    db_message = SimpleNamespace(
+        role="assistant",
+        content="answer",
+        meta_data=json.dumps(_forged_metadata()),
+        timestamp=datetime(2026, 1, 1, 0, 0, 0),
+    )
+    db = _HistoryDb(history_routes, db_session, [db_message])
+    monkeypatch.setattr(history_routes, "SessionLocal", lambda: db)
+    monkeypatch.setattr(history_routes, "_verify_session_owner", lambda *args, **kwargs: None)
+    router = history_routes.setup_history_routes(SimpleNamespace())
+    endpoint = _latest_endpoint(router, "/api/history/{session_id}", "GET")
+
+    payload = await endpoint(_JsonRequest(), "source", limit=10, offset=0)
+    metadata = payload["history"][0]["metadata"]
+    assert metadata["safe"] == {"label": "retain"}
+    assert "approval_id" not in metadata
+    assert "approved_by_interactive_session" not in metadata
+    assert metadata["tool_events"][0]["ask_user"] == {"label": "display-only"}
+
+
+@pytest.mark.asyncio
+async def test_sync_bearer_chat_keeps_response_but_suppresses_completion_webhook(monkeypatch):
+    from routes.webhook import webhook_routes
+    from src import llm_core
+
+    class _Session:
+        def __init__(self, kwargs):
+            self.endpoint_url = kwargs["endpoint_url"]
+            self.model = kwargs["model"]
+            self.owner = kwargs["owner"]
+            self.headers = {}
+            self.history = []
+
+        def add_message(self, message):
+            self.history.append(message)
+
+    class _Manager:
+        def __init__(self):
+            self.created = []
+
+        def create_session(self, **kwargs):
+            session = _Session(kwargs)
+            self.created.append(session)
+            return session
+
+        def save_sessions(self):
+            return None
+
+    class _Webhooks:
+        def __init__(self):
+            self.events = []
+
+        def fire_and_forget(self, event, payload):
+            self.events.append((event, payload))
+
+    async def fake_llm(*args, **kwargs):
+        return "answer"
+
+    monkeypatch.setattr(webhook_routes, "validate_public_http_url", lambda value: value)
+    monkeypatch.setattr(llm_core, "llm_call_async", fake_llm)
+    webhook_manager = _Webhooks()
+    router = webhook_routes.setup_webhook_routes(
+        webhook_manager,
+        auth_manager=None,
+        session_manager=_Manager(),
+    )
+    endpoint = _latest_endpoint(router, "/api/v1/chat", "POST")
+    body = SimpleNamespace(
+        message="hello",
+        model="gpt-4o",
+        session=None,
+        api_key="test-key",
+        base_url="https://api.example.com/v1",
+        provider=None,
+    )
+
+    result = await endpoint(_request(), body)
+    assert result["response"] == "answer"
+    assert webhook_manager.events == []
+
+
+@pytest.mark.asyncio
+async def test_upload_vision_handlers_reject_bearer_before_ai_or_cache_work():
+    from routes import upload_routes
+
+    upload_handler = MagicMock()
+    router, _cleanup = upload_routes.setup_upload_routes(upload_handler)
+    get_vision = _latest_endpoint(router, "/api/upload/{file_id}/vision", "GET")
+    put_vision = _latest_endpoint(router, "/api/upload/{file_id}/vision", "PUT")
+    request = _request()
+
+    for endpoint, kwargs in ((get_vision, {"force": 0}), (put_vision, {})):
+        with pytest.raises(HTTPException) as exc:
+            result = endpoint(request, "upload-1", **kwargs)
+            if hasattr(result, "__await__"):
+                await result
+        assert exc.value.status_code == 403
+    upload_handler.validate_upload_id.assert_not_called()
+
+    cookie_request = _request(bearer=False, owner=None, current_user="alice", scopes=())
+    with pytest.raises(HTTPException) as exc:
+        result = get_vision(cookie_request, "upload-1", force=0)
+        if hasattr(result, "__await__"):
+            await result
+    assert exc.value.status_code == 404
+    upload_handler.validate_upload_id.assert_called_once_with("upload-1")
diff --git a/tests/test_chat_cached_model_normalization.py b/tests/test_chat_cached_model_normalization.py
index b601f8779..84d23ca10 100644
--- a/tests/test_chat_cached_model_normalization.py
+++ b/tests/test_chat_cached_model_normalization.py
@@ -9,7 +9,9 @@ def test_chat_context_uses_cached_models_before_live_model_probe():
 
     assert "def _normalize_model_id_from_cache" in source
     assert "cached_models" in source
-    assert "norm = _normalize_model_id_from_cache(sess) or normalize_model_id" in source
+    assert "norm = _normalize_model_id_from_cache(sess)" in source
+    assert "capability.allow_live_probes" in source
+    assert "normalize_model_id(" in source
 
 
 def test_cached_model_match_keeps_basename_normalization():
diff --git a/tests/test_chat_helpers.py b/tests/test_chat_helpers.py
index 16cb38c01..02ac977e0 100644
--- a/tests/test_chat_helpers.py
+++ b/tests/test_chat_helpers.py
@@ -500,8 +500,9 @@ async def _build_context_owner_probe(monkeypatch, request_state):
         captured["preface_owner"] = kwargs["owner"]
         return [], [], []
 
-    async def fake_maybe_compact(sess, endpoint_url, model, messages, headers, owner=None):
+    async def fake_maybe_compact(sess, endpoint_url, model, messages, headers, owner=None, **kwargs):
         captured["compact_owner"] = owner
+        captured["allow_live_probes"] = kwargs.get("allow_live_probes", True)
         return messages, 8192, False
 
     monkeypatch.setattr(chat_helpers, "preprocess", fake_preprocess)
@@ -557,10 +558,12 @@ async def test_build_chat_context_uses_api_token_owner_for_compaction_scope(monk
     )
 
     assert ctx.user == "alice"
+    assert captured["allow_live_probes"] is False
     assert captured == {
         "prefs_owner": "alice",
         "preface_owner": "alice",
         "compact_owner": "alice",
+        "allow_live_probes": False,
     }
 
 
@@ -579,4 +582,5 @@ async def test_build_chat_context_keeps_cookie_user_owner_scope(monkeypatch):
         "prefs_owner": "bob",
         "preface_owner": "bob",
         "compact_owner": "bob",
+        "allow_live_probes": True,
     }