diff --git a/src/openjarvis/agents/errors.py b/src/openjarvis/agents/errors.py
index d130d859..6ef1e9d0 100644
--- a/src/openjarvis/agents/errors.py
+++ b/src/openjarvis/agents/errors.py
@@ -2,6 +2,8 @@
 
 from __future__ import annotations
 
+from openjarvis.engine._base import looks_like_context_length_error
+
 
 class AgentTickError(Exception):
     """Base class for agent tick errors."""
@@ -64,6 +66,14 @@ def classify_error(exc: Exception) -> AgentTickError:
 
     msg = str(exc).lower()
 
+    # A context-window overflow is deterministic: retrying the identical
+    # over-length request can never succeed, so fail fast instead of burning
+    # the retry budget on it.
+    if getattr(exc, "is_context_length_error", False) or (
+        looks_like_context_length_error(msg)
+    ):
+        return FatalError(str(exc))
+
     # Check fatal patterns first (more specific)
     if isinstance(exc, PermissionError):
         return FatalError(str(exc))
@@ -90,6 +100,11 @@ def retry_delay(attempt: int) -> int:
 def suggest_action(error: AgentTickError) -> str:
     """Return a human-readable suggested action for the given error."""
     msg = str(error).lower()
+    if looks_like_context_length_error(msg):
+        return (
+            "Conversation too long for the model's context window \u2014 "
+            "start a new chat or shorten the conversation"
+        )
     if any(p in msg for p in ("rate limit", "rate_limit", "429", "too many requests")):
         return "Rate limited \u2014 agent will auto-retry on next tick"
     if any(p in msg for p in ("timeout", "timed out", "connection", "unavailable")):
diff --git a/src/openjarvis/agents/hybrid/mini_swe_agent.py b/src/openjarvis/agents/hybrid/mini_swe_agent.py
index 1fe563ce..e4023e02 100644
--- a/src/openjarvis/agents/hybrid/mini_swe_agent.py
+++ b/src/openjarvis/agents/hybrid/mini_swe_agent.py
@@ -1403,12 +1403,10 @@ def _loop_local(
             # server walled the call. Compact aggressively (keep_last=1)
             # and retry once. Re-raise on anything else or on a second
             # failure — the runner records the row as errored.
+            from openjarvis.engine._base import looks_like_context_length_error
+
             msg = str(exc)
-            is_ctx = (
-                "maximum context length" in msg
-                or "context length" in msg.lower()
-                and "exceed" in msg.lower()
-            )
+            is_ctx = looks_like_context_length_error(msg)
             if not is_ctx:
                 raise
             _record_event(
diff --git a/src/openjarvis/cli/ask.py b/src/openjarvis/cli/ask.py
index 17b9ccbd..b10fc88a 100644
--- a/src/openjarvis/cli/ask.py
+++ b/src/openjarvis/cli/ask.py
@@ -20,6 +20,7 @@ from openjarvis.core.events import EventBus, EventType
 from openjarvis.core.types import Message, Role
 from openjarvis.engine import (
     EngineConnectionError,
+    EngineContextLengthError,
     discover_engines,
     discover_models,
     get_engine,
@@ -881,6 +882,11 @@ def ask(
                 capability_policy=sec.capability_policy,
                 memory_files_config=effective_mf,
             )
+        except EngineContextLengthError as exc:
+            # Not a reachability problem — pointing the user at server/host
+            # config (hint_no_engine) would be misleading here.
+            console.print(f"[red]{exc}[/red]")
+            sys.exit(1)
         except EngineConnectionError as exc:
             console.print(f"[red]Engine error:[/red] {exc}")
             console.print(hint_no_engine())
@@ -990,6 +996,11 @@ def ask(
                 temperature=temperature,
                 max_tokens=max_tokens,
             )
+    except EngineContextLengthError as exc:
+        # Not a reachability problem — pointing the user at server/host
+        # config (hint_no_engine) would be misleading here.
+        console.print(f"[red]{exc}[/red]")
+        sys.exit(1)
     except EngineConnectionError as exc:
         console.print(f"[red]Engine error:[/red] {exc}")
         console.print(hint_no_engine())
diff --git a/src/openjarvis/engine/__init__.py b/src/openjarvis/engine/__init__.py
index 90486fe6..d575da8f 100644
--- a/src/openjarvis/engine/__init__.py
+++ b/src/openjarvis/engine/__init__.py
@@ -9,7 +9,9 @@ import openjarvis.engine.ollama  # noqa: F401
 import openjarvis.engine.openai_compat_engines  # noqa: F401
 from openjarvis.engine._base import (
     EngineConnectionError,
+    EngineContextLengthError,
     InferenceEngine,
+    looks_like_context_length_error,
     messages_to_dicts,
 )
 from openjarvis.engine._discovery import discover_engines, discover_models, get_engine
@@ -23,9 +25,11 @@ for _optional in ("cloud", "litellm", "gemma_cpp"):
 
 __all__ = [
     "EngineConnectionError",
+    "EngineContextLengthError",
     "InferenceEngine",
     "discover_engines",
     "discover_models",
     "get_engine",
+    "looks_like_context_length_error",
     "messages_to_dicts",
 ]
diff --git a/src/openjarvis/engine/_base.py b/src/openjarvis/engine/_base.py
index 6ecaf81a..102936ba 100644
--- a/src/openjarvis/engine/_base.py
+++ b/src/openjarvis/engine/_base.py
@@ -13,6 +13,46 @@ class EngineConnectionError(Exception):
     """Raised when an engine is unreachable."""
 
 
+class EngineContextLengthError(EngineConnectionError):
+    """The prompt exceeds the served model's maximum context window.
+
+    Subclasses ``EngineConnectionError`` so existing ``except
+    EngineConnectionError`` handlers keep catching it, while callers that want a
+    distinct, user-facing "conversation too long" message can branch on this type
+    (or the ``is_context_length_error`` marker) instead of surfacing a generic
+    engine failure.
+    """
+
+    is_context_length_error: bool = True
+
+
+# Substrings that identify an error body as a context-window overflow (vLLM,
+# SGLang, and OpenAI-compatible servers phrase this a few different ways).
+# Every marker is anchored on "context" on purpose: generic phrases like
+# "please reduce" or "too many tokens" also appear in unrelated 400 bodies
+# (max_tokens validation, rate limiting, oversized images) and would
+# misclassify those as "conversation too long".
+CONTEXT_LENGTH_MARKERS = (
+    "context length",
+    "maximum context",
+    "context window",
+    "maximum_context",
+    "context_length_exceeded",
+)
+
+
+def looks_like_context_length_error(text: str) -> bool:
+    """True when *text* reads like a context-window overflow error.
+
+    The single shared heuristic for recognizing vendor context-overflow
+    phrasings — used by the engine layer (typing upstream 400s), agent error
+    classification, and the server stream bridge, so a new vendor phrasing
+    only ever needs to be added here.
+    """
+    low = (text or "").lower()
+    return any(marker in low for marker in CONTEXT_LENGTH_MARKERS)
+
+
 _REASONING_METADATA_KEYS = ("reasoning_content", "thinking")
 
 
@@ -80,8 +120,11 @@ def estimate_prompt_tokens(messages: Sequence[Message]) -> int:
 
 
 __all__ = [
+    "CONTEXT_LENGTH_MARKERS",
     "EngineConnectionError",
+    "EngineContextLengthError",
     "InferenceEngine",
     "estimate_prompt_tokens",
+    "looks_like_context_length_error",
     "messages_to_dicts",
 ]
diff --git a/src/openjarvis/engine/_http_async.py b/src/openjarvis/engine/_http_async.py
new file mode 100644
index 00000000..cc1239a2
--- /dev/null
+++ b/src/openjarvis/engine/_http_async.py
@@ -0,0 +1,128 @@
+"""Shared async-HTTP plumbing for engines that stream over httpx.
+
+Home of the pieces the OpenAI-compat and Ollama engines were each hand-rolling:
+the async-client factory (with the configured timeout applied), a cached
+long-lived client so consecutive streams reuse pooled connections instead of
+paying a fresh TCP/TLS handshake per turn, the transport-error set that maps to
+``EngineConnectionError``, and the non-2xx → engine-error translation.
+"""
+
+from __future__ import annotations
+
+import asyncio
+import logging
+from typing import NoReturn
+
+import httpx
+
+from openjarvis.engine._base import (
+    EngineConnectionError,
+    EngineContextLengthError,
+    looks_like_context_length_error,
+)
+
+logger = logging.getLogger(__name__)
+
+# Transport failures that map to EngineConnectionError on the streaming paths.
+# ``RemoteProtocolError``/``ReadError`` cover a server dying MID-STREAM (peer
+# closed between tokens); a wedged read trips the configured timeout
+# (TimeoutException). Kept exactly this narrow on purpose:
+# ``asyncio.CancelledError``/``GeneratorExit`` are NOT ``httpx.TransportError``
+# subclasses and must keep propagating for correct cancellation.
+STREAM_TRANSPORT_ERRORS = (
+    httpx.ConnectError,
+    httpx.TimeoutException,
+    httpx.RemoteProtocolError,
+    httpx.ReadError,
+)
+
+_CONTEXT_LENGTH_USER_MESSAGE = (
+    "The conversation is too long for the model's context window. "
+    "Start a new chat or shorten the conversation, then try again."
+)
+
+
+class AsyncHTTPEngineMixin:
+    """Async streaming plumbing shared by httpx-backed engines.
+
+    Expects the engine to provide ``engine_id``, ``_host``, ``_timeout``, an
+    ``_async_transport`` test seam (``httpx.MockTransport`` in tests, ``None``
+    in production), and optionally ``_headers``.
+    """
+
+    engine_id: str
+    _host: str
+    _timeout: float
+    _async_transport: httpx.AsyncBaseTransport | None
+
+    # Set True by engines whose upstream reports context-window overflows in
+    # 400 bodies (OpenAI-compat servers). Ollama has no such signal.
+    _stream_400_signals_context_length: bool = False
+
+    # Lazily-created shared client (and the loop it belongs to). Class-level
+    # ``None`` defaults keep engine ``__init__``s free of mixin bookkeeping.
+    _async_client: httpx.AsyncClient | None = None
+    _async_client_loop: asyncio.AbstractEventLoop | None = None
+
+    def _make_async_client(self) -> httpx.AsyncClient:
+        """Build an async client that honours the configured timeout."""
+        return httpx.AsyncClient(
+            base_url=self._host,
+            timeout=self._timeout,
+            headers=getattr(self, "_headers", None),
+            transport=self._async_transport,
+        )
+
+    def _get_async_client(self) -> httpx.AsyncClient:
+        """Return the shared async client for the running event loop.
+
+        Reusing one client across calls preserves connection pooling — without
+        it every conversation turn pays a fresh TCP (and TLS) handshake. The
+        client is cached per event loop: pooled connections die with their
+        loop, so CLI flows that run ``asyncio.run()`` per turn transparently
+        get a fresh client while a long-lived server loop keeps one pool.
+        """
+        loop = asyncio.get_running_loop()
+        client = self._async_client
+        if client is None or client.is_closed or self._async_client_loop is not loop:
+            # Any previous client belonged to a finished loop; its pooled
+            # connections are already dead, so just drop the reference.
+            client = self._make_async_client()
+            self._async_client = client
+            self._async_client_loop = loop
+        return client
+
+    def _close_async_client(self) -> None:
+        """Best-effort close of the shared async client (for ``close()``)."""
+        client = self._async_client
+        loop = self._async_client_loop
+        self._async_client = None
+        self._async_client_loop = None
+        if client is None or client.is_closed:
+            return
+        try:
+            if loop is not None and not loop.is_closed():
+                if loop.is_running():
+                    loop.create_task(client.aclose())
+                else:
+                    loop.run_until_complete(client.aclose())
+        except Exception:  # noqa: BLE001 — cleanup must never mask the close
+            logger.debug("Async client did not close cleanly", exc_info=True)
+
+    def _raise_stream_http_error(self, status: int, detail: str) -> NoReturn:
+        """Map a non-success streaming HTTP response to a clean engine error."""
+        detail = (detail or "").strip()
+        if (
+            status == 400
+            and self._stream_400_signals_context_length
+            and looks_like_context_length_error(detail)
+        ):
+            raise EngineContextLengthError(_CONTEXT_LENGTH_USER_MESSAGE)
+        detail_suffix = f": {detail}" if detail else ""
+        raise EngineConnectionError(
+            f"{self.engine_id} engine at {self._host} returned HTTP "
+            f"{status}{detail_suffix}"
+        )
+
+
+__all__ = ["AsyncHTTPEngineMixin", "STREAM_TRANSPORT_ERRORS"]
diff --git a/src/openjarvis/engine/_openai_compat.py b/src/openjarvis/engine/_openai_compat.py
index 5f767478..507b6d83 100644
--- a/src/openjarvis/engine/_openai_compat.py
+++ b/src/openjarvis/engine/_openai_compat.py
@@ -12,18 +12,27 @@ import httpx
 from openjarvis.core.types import Message
 from openjarvis.engine._base import (
     EngineConnectionError,
+    EngineContextLengthError,
     InferenceEngine,
     estimate_prompt_tokens,
     messages_to_dicts,
 )
+from openjarvis.engine._http_async import (
+    STREAM_TRANSPORT_ERRORS,
+    AsyncHTTPEngineMixin,
+)
 from openjarvis.engine._stubs import StreamChunk
 
 logger = logging.getLogger(__name__)
 
 
-class _OpenAICompatibleEngine(InferenceEngine):
+class _OpenAICompatibleEngine(AsyncHTTPEngineMixin, InferenceEngine):
     """Base for engines that serve the OpenAI ``/v1/chat/completions`` API."""
 
+    # vLLM/SGLang report context-window overflows in 400 bodies; the shared
+    # ``_raise_stream_http_error`` types those as ``EngineContextLengthError``.
+    _stream_400_signals_context_length = True
+
     engine_id: str = ""
     _default_host: str = "http://localhost:8000"
     _api_prefix: str = "/v1"
@@ -50,6 +59,16 @@ class _OpenAICompatibleEngine(InferenceEngine):
         headers = (
             {"Authorization": f"Bearer {self._api_key}"} if self._api_key else None
         )
+        # Used by the shared async streaming plumbing (AsyncHTTPEngineMixin) so
+        # the bounded request timeout is applied to streaming reads, not just
+        # the synchronous methods (a wedged token read fails at ``timeout``
+        # rather than hanging the caller for the httpx default).
+        self._timeout = timeout
+        self._headers = headers
+        # Injection seam for tests: an ``httpx.MockTransport`` swapped in here lets
+        # the async stream path be exercised with a mocked transport and no real
+        # server. ``None`` in production so httpx uses its default networking.
+        self._async_transport: httpx.AsyncBaseTransport | None = None
         self._client = httpx.Client(
             base_url=self._host, timeout=timeout, headers=headers
         )
@@ -168,11 +187,26 @@ class _OpenAICompatibleEngine(InferenceEngine):
         # Default to tool_choice=auto when tools are provided
         if "tools" in payload and "tool_choice" not in payload:
             payload["tool_choice"] = "auto"
+        url = f"{self._api_prefix}/chat/completions"
         try:
-            url = f"{self._api_prefix}/chat/completions"
-            with self._client.stream("POST", url, json=payload) as resp:
-                resp.raise_for_status()
-                for line in resp.iter_lines():
+            # ASYNC streaming: ``httpx.AsyncClient`` + ``aiter_lines`` never
+            # blocks the event loop between tokens (the previous SYNC
+            # ``httpx.Client`` + ``iter_lines`` inside this ``async def`` blocked
+            # the single uvicorn worker on every inter-token wait, serializing all
+            # concurrent chats and letting one wedged read freeze the whole API).
+            # The shared client keeps pooled connections across turns.
+            client = self._get_async_client()
+            async with client.stream("POST", url, json=payload) as resp:
+                # ``not is_success`` covers 3xx as well as 4xx/5xx. With
+                # ``follow_redirects`` off (the default) an unexpected redirect
+                # would otherwise fall through to ``aiter_lines`` and surface as
+                # a silent EMPTY stream instead of a clean engine error.
+                if not resp.is_success:
+                    # Load the (short) error body before touching ``.text``:
+                    # a streaming response is otherwise unread.
+                    await resp.aread()
+                    self._raise_stream_http_error(resp.status_code, resp.text)
+                async for line in resp.aiter_lines():
                     if not line.startswith("data:"):
                         continue
                     data_str = line[len("data:") :].strip()
@@ -186,7 +220,11 @@ class _OpenAICompatibleEngine(InferenceEngine):
                     content = delta.get("content")
                     if content:
                         yield content
-        except (httpx.ConnectError, httpx.TimeoutException) as exc:
+        except STREAM_TRANSPORT_ERRORS as exc:
+            # A wedged upstream read trips ``timeout`` (ReadTimeout) and is mapped
+            # here, so the request fails cleanly at the configured bound instead
+            # of hanging indefinitely (see STREAM_TRANSPORT_ERRORS for why the
+            # set is exactly this narrow).
             raise EngineConnectionError(
                 f"{self.engine_id} engine not reachable at {self._host}"
             ) from exc
@@ -212,11 +250,20 @@ class _OpenAICompatibleEngine(InferenceEngine):
         }
         if "tools" in payload and "tool_choice" not in payload:
             payload["tool_choice"] = "auto"
+        url = f"{self._api_prefix}/chat/completions"
         try:
-            url = f"{self._api_prefix}/chat/completions"
-            with self._client.stream("POST", url, json=payload) as resp:
-                resp.raise_for_status()
-                for line in resp.iter_lines():
+            # ASYNC streaming (see ``stream``): non-blocking shared client so
+            # rich streaming never stalls the event loop and honours ``timeout``.
+            client = self._get_async_client()
+            async with client.stream("POST", url, json=payload) as resp:
+                # ``not is_success`` covers 3xx as well as 4xx/5xx. With
+                # ``follow_redirects`` off (the default) an unexpected redirect
+                # would otherwise fall through to ``aiter_lines`` and surface as
+                # a silent EMPTY stream instead of a clean engine error.
+                if not resp.is_success:
+                    await resp.aread()
+                    self._raise_stream_http_error(resp.status_code, resp.text)
+                async for line in resp.aiter_lines():
                     if not line.startswith("data:"):
                         continue
                     data_str = line[len("data:") :].strip()
@@ -240,7 +287,10 @@ class _OpenAICompatibleEngine(InferenceEngine):
                             finish_reason=finish,
                             usage=usage,
                         )
-        except (httpx.ConnectError, httpx.TimeoutException) as exc:
+        except STREAM_TRANSPORT_ERRORS as exc:
+            # See ``stream``: transport failures (incl. a mid-stream server
+            # disconnect) map to a clean error; the set is kept narrow so
+            # cancellation still propagates.
             raise EngineConnectionError(
                 f"{self.engine_id} engine not reachable at {self._host}"
             ) from exc
@@ -279,6 +329,9 @@ class _OpenAICompatibleEngine(InferenceEngine):
 
     def close(self) -> None:
         self._client.close()
+        self._close_async_client()
 
 
-__all__ = ["_OpenAICompatibleEngine"]
+# ``EngineContextLengthError`` moved to ``openjarvis.engine._base``; re-exported
+# here for callers/tests that import it from this module.
+__all__ = ["_OpenAICompatibleEngine", "EngineContextLengthError"]
diff --git a/src/openjarvis/engine/litellm.py b/src/openjarvis/engine/litellm.py
index a90ec474..6e9c114b 100644
--- a/src/openjarvis/engine/litellm.py
+++ b/src/openjarvis/engine/litellm.py
@@ -123,8 +123,12 @@ class LiteLLMEngine(InferenceEngine):
             call_kwargs["api_base"] = self._api_base
         call_kwargs.update(kwargs)
 
-        resp = litellm.completion(**call_kwargs)
-        for chunk in resp:
+        # ``acompletion`` + ``async for``: the sync ``litellm.completion`` used
+        # before made a blocking network call (and blocking per-chunk reads)
+        # inside this ``async def``, stalling the whole event loop between
+        # tokens — the same bug the httpx engines' streaming paths had.
+        resp = await litellm.acompletion(**call_kwargs)
+        async for chunk in resp:
             delta = chunk.choices[0].delta if chunk.choices else None
             if delta and delta.content:
                 yield delta.content
diff --git a/src/openjarvis/engine/ollama.py b/src/openjarvis/engine/ollama.py
index c959d44f..ae07e3cc 100644
--- a/src/openjarvis/engine/ollama.py
+++ b/src/openjarvis/engine/ollama.py
@@ -18,6 +18,10 @@ from openjarvis.engine._base import (
     estimate_prompt_tokens,
     messages_to_dicts,
 )
+from openjarvis.engine._http_async import (
+    STREAM_TRANSPORT_ERRORS,
+    AsyncHTTPEngineMixin,
+)
 from openjarvis.engine._stubs import StreamChunk
 
 logger = logging.getLogger(__name__)
@@ -80,11 +84,15 @@ def _default_num_ctx() -> int:
 
 
 @EngineRegistry.register("ollama")
-class OllamaEngine(InferenceEngine):
+class OllamaEngine(AsyncHTTPEngineMixin, InferenceEngine):
     """Ollama backend via its native HTTP API."""
 
     engine_id = "ollama"
 
+    # Ollama has no context-length overflow signal in its 400 bodies, so the
+    # shared ``_raise_stream_http_error`` keeps its default (no
+    # ``EngineContextLengthError`` branch, unlike the OpenAI-compat engines).
+
     _DEFAULT_HOST = "http://localhost:11434"
 
     def __init__(
@@ -98,6 +106,14 @@ class OllamaEngine(InferenceEngine):
             env_host = os.environ.get("OLLAMA_HOST")
             host = env_host or self._DEFAULT_HOST
         self._host = host.rstrip("/")
+        # Used by the shared async streaming plumbing (AsyncHTTPEngineMixin) so a
+        # wedged token read is bounded by ``timeout`` instead of hanging the
+        # single event loop for the httpx default.
+        self._timeout = timeout
+        # Injection seam for tests: an ``httpx.MockTransport`` swapped in here drives
+        # the async stream path with no real Ollama server. ``None`` in production so
+        # httpx uses its default networking.
+        self._async_transport: httpx.AsyncBaseTransport | None = None
         self._client = httpx.Client(base_url=self._host, timeout=timeout)
         # Last stream usage — captured from Ollama's final chunk
         self._last_stream_usage: Dict[str, int] = {}
@@ -263,9 +279,26 @@ class OllamaEngine(InferenceEngine):
         elif kwargs["think"] is not None:
             payload["think"] = kwargs["think"]
         try:
-            with self._client.stream("POST", "/api/chat", json=payload) as resp:
-                resp.raise_for_status()
-                for line in resp.iter_lines():
+            # ASYNC streaming: ``httpx.AsyncClient`` + ``aiter_lines`` never
+            # blocks the event loop between tokens (the previous SYNC
+            # ``self._client`` + ``iter_lines`` inside this ``async def`` blocked
+            # the single uvicorn worker on every inter-token wait, serializing all
+            # concurrent chats and letting one wedged read freeze the whole API).
+            # The shared client keeps pooled connections across turns.
+            client = self._get_async_client()
+            async with client.stream("POST", "/api/chat", json=payload) as resp:
+                # ``not is_success`` covers 3xx as well as 4xx/5xx and maps
+                # to ``EngineConnectionError`` (matching the OpenAI-compat
+                # path) instead of leaking a raw ``httpx.HTTPStatusError``.
+                # With redirects off (the default) an unexpected 3xx would
+                # otherwise fall through to ``aiter_lines`` and surface as a
+                # silent EMPTY stream rather than a clean engine error.
+                if not resp.is_success:
+                    # Read the (short) error body before touching ``.text``:
+                    # a streaming response is otherwise unread.
+                    await resp.aread()
+                    self._raise_stream_http_error(resp.status_code, resp.text)
+                async for line in resp.aiter_lines():
                     if not line.strip():
                         continue
                     try:
@@ -290,7 +323,10 @@ class OllamaEngine(InferenceEngine):
                             "total_tokens": full_prompt + comp,
                         }
                         break
-        except (httpx.ConnectError, httpx.TimeoutException) as exc:
+        except STREAM_TRANSPORT_ERRORS as exc:
+            # Transport failures (incl. a mid-stream server disconnect) map to a
+            # clean error; the set is kept narrow (see STREAM_TRANSPORT_ERRORS)
+            # so cancellation still propagates.
             raise EngineConnectionError(
                 f"Ollama not reachable at {self._host}"
             ) from exc
@@ -356,19 +392,34 @@ class OllamaEngine(InferenceEngine):
     ) -> AsyncIterator[StreamChunk]:
         """Execute the streaming request and yield parsed StreamChunks."""
         try:
-            with self._client.stream("POST", "/api/chat", json=payload) as resp:
+            # ASYNC streaming (see ``stream``): shared ``AsyncClient`` +
+            # ``aiter_lines`` so rich streaming never stalls the event loop and
+            # honours ``timeout``.
+            client = self._get_async_client()
+            async with client.stream("POST", "/api/chat", json=payload) as resp:
                 if resp.status_code == 400 and retry_without_tools:
                     # Model doesn't support tools — retry without them.
+                    # PRESERVED: this specific 400 path must still trigger the
+                    # tools-less retry; only OTHER non-2xx responses map to
+                    # EngineConnectionError below.
                     payload.pop("tools", None)
                     async for c in self._run_stream(
                         payload, messages, retry_without_tools=False
                     ):
                         yield c
                     return
-                resp.raise_for_status()
+                # ``not is_success`` covers 3xx as well as 4xx/5xx and maps
+                # to ``EngineConnectionError`` (matching the OpenAI-compat
+                # path) instead of leaking a raw ``httpx.HTTPStatusError``.
+                # With redirects off (the default) an unexpected 3xx would
+                # otherwise fall through to ``aiter_lines`` and surface as a
+                # silent EMPTY stream rather than a clean engine error.
+                if not resp.is_success:
+                    await resp.aread()
+                    self._raise_stream_http_error(resp.status_code, resp.text)
 
                 finish_reason: str | None = None
-                for line in resp.iter_lines():
+                async for line in resp.aiter_lines():
                     if not line.strip():
                         continue
                     try:
@@ -441,7 +492,10 @@ class OllamaEngine(InferenceEngine):
                             usage=dict(self._last_stream_usage),
                         )
                         break
-        except (httpx.ConnectError, httpx.TimeoutException) as exc:
+        except STREAM_TRANSPORT_ERRORS as exc:
+            # See ``stream``: transport failures (incl. a mid-stream server
+            # disconnect) map to a clean error; the set is kept narrow so
+            # cancellation still propagates.
             raise EngineConnectionError(
                 f"Ollama not reachable at {self._host}"
             ) from exc
@@ -474,6 +528,7 @@ class OllamaEngine(InferenceEngine):
 
     def close(self) -> None:
         self._client.close()
+        self._close_async_client()
 
 
 __all__ = ["OllamaEngine"]
diff --git a/src/openjarvis/server/api_routes.py b/src/openjarvis/server/api_routes.py
index cac2623c..b70b4f5e 100644
--- a/src/openjarvis/server/api_routes.py
+++ b/src/openjarvis/server/api_routes.py
@@ -741,8 +741,11 @@ async def websocket_chat_stream(websocket: WebSocket):
                                 )
                     except TypeError:
                         # stream() didn't return an iterable; fall back to
-                        # generate()
-                        result = engine.generate(messages, model=model)
+                        # generate(). It makes a blocking upstream call, so run
+                        # it in a worker thread to keep the event loop free.
+                        result = await asyncio.to_thread(
+                            engine.generate, messages, model=model
+                        )
                         content = (
                             result.get("content", "")
                             if isinstance(
@@ -767,8 +770,11 @@ async def websocket_chat_stream(websocket: WebSocket):
                         ended_at=_time.time(),
                     )
                 else:
-                    # No stream method — single-shot generate
-                    result = engine.generate(messages, model=model)
+                    # No stream method — single-shot generate. Blocking upstream
+                    # call, so run in a worker thread to keep the event loop free.
+                    result = await asyncio.to_thread(
+                        engine.generate, messages, model=model
+                    )
                     content = (
                         result.get("content", "")
                         if isinstance(
diff --git a/src/openjarvis/server/routes.py b/src/openjarvis/server/routes.py
index cda60f56..ec8f187e 100644
--- a/src/openjarvis/server/routes.py
+++ b/src/openjarvis/server/routes.py
@@ -231,8 +231,13 @@ async def chat_completions(request_body: ChatCompletionRequest, request: Request
     # tools (e.g. injecting MCP tools through this endpoint and wanting
     # the agent to execute them), add an explicit opt-in header rather
     # than removing this guard — silent re-routing is what produced #414.
+    # ``_handle_agent`` (sync ``agent.run()``) and ``_handle_direct`` (sync
+    # ``engine.generate()``) both make blocking upstream calls; run them in a
+    # worker thread so a slow/wedged non-streaming request can't stall the
+    # event loop and every other concurrent request with it.
     if agent is not None and not request_body.tools:
-        response = _handle_agent(
+        response = await asyncio.to_thread(
+            _handle_agent,
             agent,
             model,
             request_body,
@@ -242,7 +247,8 @@ async def chat_completions(request_body: ChatCompletionRequest, request: Request
         )
     else:
         bus = getattr(request.app.state, "bus", None)
-        response = _handle_direct(
+        response = await asyncio.to_thread(
+            _handle_direct,
             engine,
             model,
             request_body,
diff --git a/src/openjarvis/server/stream_bridge.py b/src/openjarvis/server/stream_bridge.py
index 386a677f..6d331021 100644
--- a/src/openjarvis/server/stream_bridge.py
+++ b/src/openjarvis/server/stream_bridge.py
@@ -16,6 +16,7 @@ from fastapi.responses import StreamingResponse
 
 from openjarvis.agents._stubs import AgentContext, BaseAgent
 from openjarvis.core.events import Event, EventBus, EventType
+from openjarvis.engine._base import looks_like_context_length_error
 from openjarvis.server.models import (
     ChatCompletionChunk,
     ChatCompletionRequest,
@@ -194,8 +195,10 @@ class AgentStreamBridge:
                 logger.error("Agent stream error: %s", exc, exc_info=True)
 
                 error_str = str(exc)
-                if "context length" in error_str.lower() or (
-                    "400" in error_str and "too long" in error_str.lower()
+                if (
+                    getattr(exc, "is_context_length_error", False)
+                    or looks_like_context_length_error(error_str)
+                    or ("400" in error_str and "too long" in error_str.lower())
                 ):
                     error_content = (
                         "The input is too long for the model's context window. "
diff --git a/tests/agents/test_errors.py b/tests/agents/test_errors.py
index 72b7ae46..94341912 100644
--- a/tests/agents/test_errors.py
+++ b/tests/agents/test_errors.py
@@ -56,3 +56,30 @@ class TestErrorClassification:
         assert retry_delay(2) == 40
         # Capped at 300 seconds
         assert retry_delay(10) == 300
+
+    def test_classify_context_length_is_fatal(self):
+        # A context-window overflow is deterministic — retrying the identical
+        # over-length request can never succeed, so it must NOT be classified
+        # retryable (which would burn ~30s of backoff on guaranteed failures).
+        from openjarvis.agents.errors import classify_error
+        from openjarvis.engine._base import EngineContextLengthError
+
+        typed = classify_error(
+            EngineContextLengthError(
+                "The conversation is too long for the model's context window."
+            )
+        )
+        assert typed.retryable is False
+
+        # Same for untyped errors whose message reads like a context overflow
+        # (e.g. raw vendor errors from engines without the typed mapping).
+        untyped = classify_error(
+            Exception("This model's maximum context length is 4096 tokens.")
+        )
+        assert untyped.retryable is False
+
+    def test_suggest_action_context_length(self):
+        from openjarvis.agents.errors import FatalError, suggest_action
+
+        action = suggest_action(FatalError("prompt exceeds the model's context window"))
+        assert "context window" in action or "too long" in action.lower()
diff --git a/tests/engine/test_litellm.py b/tests/engine/test_litellm.py
index b46b5b61..ed8793ed 100644
--- a/tests/engine/test_litellm.py
+++ b/tests/engine/test_litellm.py
@@ -158,6 +158,9 @@ class TestLiteLLMEngineGenerate:
 
 class TestLiteLLMEngineStream:
     def test_stream(self) -> None:
+        # stream() must use the ASYNC litellm entry point (acompletion): the
+        # sync litellm.completion makes blocking network reads inside an
+        # ``async def``, stalling the event loop between tokens.
         chunk1 = SimpleNamespace(
             choices=[SimpleNamespace(delta=SimpleNamespace(content="Hel"))]
         )
@@ -168,8 +171,12 @@ class TestLiteLLMEngineStream:
             choices=[SimpleNamespace(delta=SimpleNamespace(content=None))]
         )
 
+        async def _chunks():
+            for c in (chunk1, chunk2, chunk3):
+                yield c
+
         fake_litellm = mock.MagicMock()
-        fake_litellm.completion.return_value = iter([chunk1, chunk2, chunk3])
+        fake_litellm.acompletion = mock.AsyncMock(return_value=_chunks())
 
         with mock.patch.dict("sys.modules", {"litellm": fake_litellm}):
             engine = LiteLLMEngine()
@@ -186,6 +193,8 @@ class TestLiteLLMEngineStream:
             tokens = asyncio.run(collect())
 
         assert tokens == ["Hel", "lo!"]
+        fake_litellm.acompletion.assert_awaited_once()
+        assert fake_litellm.completion.call_count == 0
 
 
 class TestLiteLLMEngineListModels:
diff --git a/tests/engine/test_ollama.py b/tests/engine/test_ollama.py
index 0e62a343..30317481 100644
--- a/tests/engine/test_ollama.py
+++ b/tests/engine/test_ollama.py
@@ -6,13 +6,27 @@ import json
 
 import httpx
 import pytest
-import respx
+
+try:
+    import respx
+
+    _HAS_RESPX = True
+except ImportError:  # respx is an optional test-only dep; the async MockTransport
+    respx = None  # type: ignore[assignment]  # pins below run without it.
+    _HAS_RESPX = False
 
 from openjarvis.core.registry import EngineRegistry
 from openjarvis.core.types import Message, Role
 from openjarvis.engine._base import EngineConnectionError
 from openjarvis.engine.ollama import OllamaEngine, _is_control_token_only_args
 
+# respx-backed tests exercise the SYNC client paths (generate/list_models/health)
+# and the respx-driven stream tests; they skip cleanly when respx is absent. The
+# async pins in TestOllamaStreamIsAsyncAndBounded use httpx.MockTransport directly.
+requires_respx = pytest.mark.skipif(
+    not _HAS_RESPX, reason="respx not installed (optional test-only dependency)"
+)
+
 
 @pytest.fixture()
 def engine() -> OllamaEngine:
@@ -20,6 +34,7 @@ def engine() -> OllamaEngine:
     return OllamaEngine(host="http://testhost:11434")
 
 
+@requires_respx
 class TestOllamaGenerate:
     def test_generate_returns_content(self, engine: OllamaEngine) -> None:
         with respx.mock:
@@ -53,6 +68,7 @@ class TestOllamaGenerate:
                 )
 
 
+@requires_respx
 class TestOllamaListModels:
     def test_list_models(self, engine: OllamaEngine) -> None:
         with respx.mock:
@@ -66,6 +82,7 @@ class TestOllamaListModels:
         assert models == ["qwen3:8b", "llama3.2:3b"]
 
 
+@requires_respx
 class TestOllamaHealth:
     def test_health_true(self, engine: OllamaEngine) -> None:
         with respx.mock:
@@ -120,6 +137,7 @@ class TestControlTokenFilter:
         assert _is_control_token_only_args(raw_args) is False
 
 
+@requires_respx
 class TestOllamaGenerateControlToken:
     def test_generate_drops_control_token_tool_call(self, engine: OllamaEngine) -> None:
         with respx.mock:
@@ -219,6 +237,7 @@ class TestOllamaGenerateControlToken:
         assert json.loads(result["tool_calls"][0]["arguments"]) == {"command": "date"}
 
 
+@requires_respx
 class TestOllamaStreamFullControlToken:
     @pytest.mark.asyncio
     async def test_stream_full_drops_control_token_tool_call(
@@ -257,6 +276,7 @@ class TestOllamaStreamFullControlToken:
         assert all(not c.tool_calls for c in chunks)
 
 
+@requires_respx
 class TestOllamaStream:
     @pytest.mark.asyncio
     async def test_stream_yields_content(self, engine: OllamaEngine) -> None:
@@ -275,3 +295,214 @@ class TestOllamaStream:
             ):
                 tokens.append(tok)
         assert "Hello" in tokens
+
+
+def _ndjson_transport(lines: list[str]) -> httpx.MockTransport:
+    body = "\n".join(lines) + "\n"
+
+    def handler(request: httpx.Request) -> httpx.Response:
+        return httpx.Response(200, text=body)
+
+    return httpx.MockTransport(handler)
+
+
+class TestOllamaStreamIsAsyncAndBounded:
+    """Regression pins: the Ollama stream paths are async (never iterate the SYNC
+    httpx client between tokens, which blocked the single uvicorn worker on every
+    inter-token wait) and a mid-stream disconnect is bounded and mapped to a clean
+    error. Uses httpx.MockTransport directly, so it runs without respx."""
+
+    @pytest.mark.asyncio
+    async def test_stream_does_not_use_blocking_sync_client(self) -> None:
+        # PIN: the old code iterated ``self._client`` (a SYNC httpx.Client) via
+        # ``iter_lines`` inside this ``async def``. The async path must not touch the
+        # sync client at all — swap in a bomb that explodes if ``.stream`` is used.
+        engine = OllamaEngine(host="http://localhost:11434")
+        engine._async_transport = _ndjson_transport(
+            [
+                json.dumps({"message": {"content": "Hi"}, "done": False}),
+                json.dumps({"message": {"content": " there"}, "done": True}),
+            ]
+        )
+
+        class _Boom:
+            def stream(self, *a, **k):  # pragma: no cover - must never run
+                raise AssertionError("streaming used the blocking sync client")
+
+        engine._client = _Boom()  # type: ignore[assignment]
+        tokens = [
+            tok
+            async for tok in engine.stream(
+                [Message(role=Role.USER, content="Hi")], model="qwen3:8b"
+            )
+        ]
+        assert tokens == ["Hi", " there"]
+
+    @pytest.mark.asyncio
+    async def test_stream_full_does_not_use_blocking_sync_client(self) -> None:
+        # stream_full delegates to _run_stream; prove that path is async too.
+        engine = OllamaEngine(host="http://localhost:11434")
+        engine._async_transport = _ndjson_transport(
+            [
+                json.dumps({"message": {"content": "Hi"}, "done": False}),
+                json.dumps(
+                    {"message": {"content": "", "tool_calls": []}, "done": True}
+                ),
+            ]
+        )
+
+        class _Boom:
+            def stream(self, *a, **k):  # pragma: no cover - must never run
+                raise AssertionError("stream_full used the blocking sync client")
+
+        engine._client = _Boom()  # type: ignore[assignment]
+        chunks = [
+            c
+            async for c in engine.stream_full(
+                [Message(role=Role.USER, content="Hi")], model="qwen3:8b"
+            )
+        ]
+        assert any(c.content == "Hi" for c in chunks)
+
+    @pytest.mark.asyncio
+    async def test_timeout_is_applied_to_async_stream_client(self) -> None:
+        # The configured timeout must be APPLIED to the async stream client, so a
+        # wedged read is actually bounded (not just stored on the engine).
+        engine = OllamaEngine(host="http://localhost:11434", timeout=0.05)
+        assert engine._timeout == 0.05
+        client = engine._make_async_client()
+        try:
+            assert client.timeout == httpx.Timeout(0.05)
+        finally:
+            await client.aclose()
+
+    @pytest.mark.asyncio
+    async def test_mid_stream_disconnect_maps_to_connection_error(self) -> None:
+        # PIN: a server dying MID-STREAM raises httpx.RemoteProtocolError from
+        # aiter_lines; it must surface as a clean EngineConnectionError, not raw.
+        class _MidStreamCrashStream(httpx.AsyncByteStream):
+            def __init__(self, request: httpx.Request) -> None:
+                self._request = request
+
+            async def __aiter__(self):
+                yield b'{"message": {"content": "Hi"}, "done": false}\n'
+                raise httpx.RemoteProtocolError(
+                    "peer closed connection mid-stream", request=self._request
+                )
+
+            async def aclose(self) -> None:  # pragma: no cover - trivial
+                pass
+
+        def handler(request: httpx.Request) -> httpx.Response:
+            return httpx.Response(200, stream=_MidStreamCrashStream(request))
+
+        engine = OllamaEngine(host="http://localhost:11434")
+        engine._async_transport = httpx.MockTransport(handler)
+        tokens: list[str] = []
+        with pytest.raises(EngineConnectionError):
+            async for tok in engine.stream(
+                [Message(role=Role.USER, content="Hi")], model="qwen3:8b"
+            ):
+                tokens.append(tok)
+        # The disconnect happened AFTER the first token was delivered (mid-stream).
+        assert tokens == ["Hi"]
+
+
+class TestOllamaStreamHttpErrorMapping:
+    """Regression pins: Ollama streaming non-2xx responses map to the same
+    ``EngineConnectionError`` as the OpenAI-compat engine (via
+    ``_raise_stream_http_error``), instead of leaking a raw
+    ``httpx.HTTPStatusError`` from ``raise_for_status()``. A 3xx must NOT fall
+    through to a silent empty stream. Uses ``httpx.MockTransport`` directly, so
+    it runs without respx."""
+
+    @staticmethod
+    def _status_transport(
+        status: int, *, text: str = "", headers: dict | None = None
+    ) -> httpx.MockTransport:
+        def handler(request: httpx.Request) -> httpx.Response:
+            return httpx.Response(status, text=text, headers=headers or {})
+
+        return httpx.MockTransport(handler)
+
+    @pytest.mark.asyncio
+    async def test_stream_500_maps_to_connection_error(self) -> None:
+        # PIN: the old code called ``resp.raise_for_status()`` and leaked a raw
+        # httpx.HTTPStatusError on a streaming 500. It must now be a clean
+        # EngineConnectionError carrying the status + body, like the compat path.
+        engine = OllamaEngine(host="http://localhost:11434")
+        engine._async_transport = self._status_transport(500, text="internal boom")
+        tokens: list[str] = []
+        with pytest.raises(EngineConnectionError) as excinfo:
+            async for tok in engine.stream(
+                [Message(role=Role.USER, content="Hi")], model="qwen3:8b"
+            ):
+                tokens.append(tok)
+        assert not isinstance(excinfo.value, httpx.HTTPStatusError)
+        assert "500" in str(excinfo.value)
+        assert "internal boom" in str(excinfo.value)
+        assert tokens == []
+
+    @pytest.mark.asyncio
+    async def test_stream_full_500_maps_to_connection_error(self) -> None:
+        # Same pin for the rich (_run_stream-backed) path.
+        engine = OllamaEngine(host="http://localhost:11434")
+        engine._async_transport = self._status_transport(500, text="internal boom")
+        with pytest.raises(EngineConnectionError) as excinfo:
+            async for _ in engine.stream_full(
+                [Message(role=Role.USER, content="Hi")], model="qwen3:8b"
+            ):
+                pass
+        assert not isinstance(excinfo.value, httpx.HTTPStatusError)
+        assert "500" in str(excinfo.value)
+        assert "internal boom" in str(excinfo.value)
+
+    @pytest.mark.asyncio
+    async def test_stream_3xx_maps_to_connection_error_not_silent(self) -> None:
+        # PIN: with redirects off, a 3xx must map to EngineConnectionError, NOT
+        # fall through to ``aiter_lines`` as a silent empty stream.
+        engine = OllamaEngine(host="http://localhost:11434")
+        engine._async_transport = self._status_transport(
+            302, headers={"location": "http://elsewhere/api/chat"}
+        )
+        tokens: list[str] = []
+        with pytest.raises(EngineConnectionError) as excinfo:
+            async for tok in engine.stream(
+                [Message(role=Role.USER, content="Hi")], model="qwen3:8b"
+            ):
+                tokens.append(tok)
+        assert "302" in str(excinfo.value)
+        assert tokens == []
+
+    @pytest.mark.asyncio
+    async def test_400_tools_retry_still_fires(self) -> None:
+        # REGRESSION GUARD: the tools-retry (400 WITH tools -> retry WITHOUT
+        # tools) must keep working; only OTHER non-2xx map to
+        # EngineConnectionError. A 400 carrying tools must NOT be treated as a
+        # generic connection error.
+        calls: list[bool] = []  # whether each request carried "tools"
+
+        def handler(request: httpx.Request) -> httpx.Response:
+            payload = json.loads(request.content)
+            had_tools = "tools" in payload
+            calls.append(had_tools)
+            if had_tools:
+                return httpx.Response(400, text="model does not support tools")
+            body = (
+                json.dumps({"message": {"content": "recovered"}, "done": True}) + "\n"
+            )
+            return httpx.Response(200, text=body)
+
+        engine = OllamaEngine(host="http://localhost:11434")
+        engine._async_transport = httpx.MockTransport(handler)
+        chunks = [
+            c
+            async for c in engine.stream_full(
+                [Message(role=Role.USER, content="Hi")],
+                model="qwen3:8b",
+                tools=[{"type": "function", "function": {"name": "shell_exec"}}],
+            )
+        ]
+        # First request had tools (400), second retried without them (200).
+        assert calls == [True, False]
+        assert any(c.content == "recovered" for c in chunks)
diff --git a/tests/engine/test_openai_compat.py b/tests/engine/test_openai_compat.py
index 31cc2af8..3df1a283 100644
--- a/tests/engine/test_openai_compat.py
+++ b/tests/engine/test_openai_compat.py
@@ -4,13 +4,37 @@ from __future__ import annotations
 
 import httpx
 import pytest
-import respx
+
+try:
+    import respx
+
+    _HAS_RESPX = True
+except ImportError:  # respx is an optional test-only dep; MockTransport tests
+    respx = None  # type: ignore[assignment]  # still run without it.
+    _HAS_RESPX = False
 
 from openjarvis.core.registry import EngineRegistry
 from openjarvis.core.types import Message, Role
 from openjarvis.engine._base import EngineConnectionError
+from openjarvis.engine._openai_compat import EngineContextLengthError
 from openjarvis.engine.openai_compat_engines import VLLMEngine
 
+# respx-backed tests exercise the SYNC client paths (generate/list_models/health)
+# and skip cleanly when respx is absent; the async stream/timeout/disconnect tests
+# below use httpx.MockTransport directly and never need respx.
+requires_respx = pytest.mark.skipif(
+    not _HAS_RESPX, reason="respx not installed (optional test-only dependency)"
+)
+
+
+def _sse_transport(sse_lines: list[str]) -> httpx.MockTransport:
+    body = "\n".join(sse_lines) + "\n"
+
+    def handler(request: httpx.Request) -> httpx.Response:
+        return httpx.Response(200, text=body)
+
+    return httpx.MockTransport(handler)
+
 
 @pytest.fixture()
 def engine() -> VLLMEngine:
@@ -18,6 +42,7 @@ def engine() -> VLLMEngine:
     return VLLMEngine(host="http://testhost:8000")
 
 
+@requires_respx
 class TestOpenAICompatGenerate:
     def test_generate_returns_content(self, engine: VLLMEngine) -> None:
         with respx.mock:
@@ -83,6 +108,7 @@ class TestOpenAICompatGenerate:
                 )
 
 
+@requires_respx
 class TestOpenAICompatListModels:
     def test_list_models(self, engine: VLLMEngine) -> None:
         with respx.mock:
@@ -95,6 +121,7 @@ class TestOpenAICompatListModels:
             assert engine.list_models() == ["model-a", "model-b"]
 
 
+@requires_respx
 class TestOpenAICompatHealth:
     def test_health_true(self, engine: VLLMEngine) -> None:
         with respx.mock:
@@ -111,6 +138,7 @@ class TestOpenAICompatHealth:
             assert engine.health() is False
 
 
+@requires_respx
 class TestOpenAICompatStream:
     @pytest.mark.asyncio
     async def test_stream_sse(self, engine: VLLMEngine) -> None:
@@ -129,3 +157,199 @@ class TestOpenAICompatStream:
             ):
                 tokens.append(tok)
         assert tokens == ["Hi", " there"]
+
+
+class TestStreamIsAsyncAndBounded:
+    """Regression pins for BC2: the stream path is async (never blocks the event
+    loop on the SYNC httpx client) and a wedged/oversized upstream is bounded and
+    mapped to a clean error instead of hanging or surfacing raw HTTP."""
+
+    @pytest.mark.asyncio
+    async def test_timeout_is_applied_to_async_stream_client(self) -> None:
+        # HARDENED: assert the configured timeout is actually APPLIED to the async
+        # stream client, not merely stored on the engine. Deleting
+        # ``timeout=self._timeout`` from ``_make_async_client`` drops the client to
+        # httpx's 5s default and fails this (a stored-only assertion would not).
+        engine = VLLMEngine(host="http://testhost:8000", timeout=180.0)
+        assert engine._timeout == 180.0
+        client = engine._make_async_client()
+        try:
+            assert client.timeout == httpx.Timeout(180.0)
+        finally:
+            await client.aclose()
+
+    @pytest.mark.asyncio
+    async def test_stream_does_not_use_blocking_sync_client(self) -> None:
+        # PIN: the old code iterated ``self._client`` (a SYNC httpx.Client) inside
+        # this ``async def``, blocking the single uvicorn worker between tokens.
+        # The async path must not touch the sync client at all.
+        engine = VLLMEngine(host="http://localhost:8000")
+        engine._async_transport = _sse_transport(
+            [
+                'data: {"choices":[{"delta":{"content":"Hi"}}]}',
+                'data: {"choices":[{"delta":{"content":" there"}}]}',
+                "data: [DONE]",
+            ]
+        )
+
+        class _Boom:
+            def stream(self, *a, **k):  # pragma: no cover - must never run
+                raise AssertionError("streaming used the blocking sync client")
+
+        engine._client = _Boom()  # type: ignore[assignment]
+        tokens = [
+            tok
+            async for tok in engine.stream(
+                [Message(role=Role.USER, content="Hello")], model="m"
+            )
+        ]
+        assert tokens == ["Hi", " there"]
+
+    @pytest.mark.asyncio
+    async def test_wedged_read_is_bounded_by_timeout(self) -> None:
+        # A wedged upstream read trips the (small, honoured) timeout and maps to a
+        # clean EngineConnectionError rather than hanging the caller.
+        seen: dict = {}
+
+        def handler(request: httpx.Request) -> httpx.Response:
+            # httpx populates request.extensions["timeout"] with the per-op timeouts
+            # that were actually applied to THIS request; capturing it here proves
+            # the configured 0.05s reached the wire, not just the engine attribute.
+            seen["timeout"] = request.extensions["timeout"]
+            raise httpx.ReadTimeout("wedged upstream", request=request)
+
+        engine = VLLMEngine(host="http://localhost:8000", timeout=0.05)
+        engine._async_transport = httpx.MockTransport(handler)
+        with pytest.raises(EngineConnectionError):
+            async for _ in engine.stream(
+                [Message(role=Role.USER, content="Hello")], model="m"
+            ):
+                pass
+        # HARDENED: the configured timeout was APPLIED to the request. Deleting
+        # ``timeout=self._timeout`` from ``_make_async_client`` drops this to httpx's
+        # 5.0s default and fails the assertion.
+        assert seen["timeout"]["read"] == 0.05
+
+    @pytest.mark.asyncio
+    async def test_context_length_400_maps_to_context_error(self) -> None:
+        def handler(request: httpx.Request) -> httpx.Response:
+            return httpx.Response(
+                400,
+                text=(
+                    "This model's maximum context length is 4096 tokens. "
+                    "However, you requested 5200 tokens. Please reduce the length."
+                ),
+            )
+
+        engine = VLLMEngine(host="http://localhost:8000")
+        engine._async_transport = httpx.MockTransport(handler)
+        with pytest.raises(EngineContextLengthError) as excinfo:
+            async for _ in engine.stream(
+                [Message(role=Role.USER, content="Hello")], model="m"
+            ):
+                pass
+        assert getattr(excinfo.value, "is_context_length_error", False) is True
+
+    @pytest.mark.asyncio
+    async def test_other_upstream_error_maps_to_connection_error(self) -> None:
+        def handler(request: httpx.Request) -> httpx.Response:
+            return httpx.Response(500, text="internal server error")
+
+        engine = VLLMEngine(host="http://localhost:8000")
+        engine._async_transport = httpx.MockTransport(handler)
+        with pytest.raises(EngineConnectionError) as excinfo:
+            async for _ in engine.stream(
+                [Message(role=Role.USER, content="Hello")], model="m"
+            ):
+                pass
+        # A generic upstream failure is NOT reported as a context-length problem.
+        assert not isinstance(excinfo.value, EngineContextLengthError)
+
+    @pytest.mark.asyncio
+    async def test_mid_stream_disconnect_maps_to_connection_error(self) -> None:
+        # PIN: a server dying MID-STREAM raises httpx.RemoteProtocolError from
+        # aiter_lines. Before the except tuple was widened it propagated raw; it
+        # must now surface as a clean EngineConnectionError.
+        class _MidStreamCrashStream(httpx.AsyncByteStream):
+            def __init__(self, request: httpx.Request) -> None:
+                self._request = request
+
+            async def __aiter__(self):
+                yield b'data: {"choices":[{"delta":{"content":"Hi"}}]}\n\n'
+                raise httpx.RemoteProtocolError(
+                    "peer closed connection mid-stream", request=self._request
+                )
+
+            async def aclose(self) -> None:  # pragma: no cover - trivial
+                pass
+
+        def handler(request: httpx.Request) -> httpx.Response:
+            return httpx.Response(200, stream=_MidStreamCrashStream(request))
+
+        engine = VLLMEngine(host="http://localhost:8000")
+        engine._async_transport = httpx.MockTransport(handler)
+        tokens: list[str] = []
+        with pytest.raises(EngineConnectionError) as excinfo:
+            async for tok in engine.stream(
+                [Message(role=Role.USER, content="Hello")], model="m"
+            ):
+                tokens.append(tok)
+        # The disconnect happened AFTER the first token was delivered (mid-stream),
+        # and did not masquerade as a context-length error.
+        assert tokens == ["Hi"]
+        assert not isinstance(excinfo.value, EngineContextLengthError)
+
+    @pytest.mark.asyncio
+    async def test_unrelated_400_is_not_context_error(self) -> None:
+        # PIN: the context-length markers are anchored on "context" so generic
+        # 400 bodies containing phrases like "please reduce" (max_tokens
+        # validation, rate limiting, oversized images) are NOT misclassified
+        # as "conversation too long" — that message would send the user off to
+        # shorten a conversation that isn't the problem.
+        def handler(request: httpx.Request) -> httpx.Response:
+            return httpx.Response(
+                400,
+                text=(
+                    "Invalid max_tokens: the maximum number of tokens you can "
+                    "request is 4096; please reduce max_tokens and retry."
+                ),
+            )
+
+        engine = VLLMEngine(host="http://localhost:8000")
+        engine._async_transport = httpx.MockTransport(handler)
+        with pytest.raises(EngineConnectionError) as excinfo:
+            async for _ in engine.stream(
+                [Message(role=Role.USER, content="Hello")], model="m"
+            ):
+                pass
+        assert not isinstance(excinfo.value, EngineContextLengthError)
+
+    @pytest.mark.asyncio
+    async def test_async_client_is_reused_across_streams(self) -> None:
+        # PIN: consecutive streams on the same event loop share one AsyncClient
+        # (connection pooling). A per-call client would pay a fresh TCP/TLS
+        # handshake on every conversation turn.
+        engine = VLLMEngine(host="http://localhost:8000")
+        engine._async_transport = _sse_transport(
+            [
+                'data: {"choices":[{"delta":{"content":"Hi"}}]}',
+                "data: [DONE]",
+            ]
+        )
+
+        async def one_turn() -> list[str]:
+            return [
+                tok
+                async for tok in engine.stream(
+                    [Message(role=Role.USER, content="Hello")], model="m"
+                )
+            ]
+
+        assert await one_turn() == ["Hi"]
+        first_client = engine._async_client
+        assert first_client is not None and not first_client.is_closed
+        assert await one_turn() == ["Hi"]
+        assert engine._async_client is first_client
+        # close() tears the shared client down with the sync one.
+        engine.close()
+        assert engine._async_client is None
diff --git a/tests/engine/test_stream_full.py b/tests/engine/test_stream_full.py
index 4003738c..94a8979a 100644
--- a/tests/engine/test_stream_full.py
+++ b/tests/engine/test_stream_full.py
@@ -5,12 +5,27 @@ from __future__ import annotations
 import json
 from collections.abc import AsyncIterator
 from typing import Any, Dict, List
-from unittest.mock import MagicMock
 
+import httpx
 import pytest
 
 from openjarvis.core.types import Message, Role
 from openjarvis.engine._stubs import InferenceEngine, StreamChunk
+from openjarvis.engine.openai_compat_engines import VLLMEngine
+
+
+def _sse_transport(sse_lines: list[str]) -> httpx.MockTransport:
+    """A MockTransport that replies to /v1/chat/completions with SSE ``sse_lines``.
+
+    Exercises the REAL async httpx streaming path (aiter_lines) with no server.
+    """
+    body = "\n".join(sse_lines) + "\n"
+
+    def handler(request: httpx.Request) -> httpx.Response:
+        return httpx.Response(200, text=body)
+
+    return httpx.MockTransport(handler)
+
 
 # ---------------------------------------------------------------------------
 # StreamChunk dataclass tests
@@ -147,8 +162,6 @@ class TestOpenAICompatStreamFull:
 
     @pytest.mark.asyncio
     async def test_parses_sse_with_content_and_finish(self):
-        from openjarvis.engine._openai_compat import _OpenAICompatibleEngine
-
         # Build mock SSE lines
         sse_lines = []
         for token in ["Hello", " world"]:
@@ -164,22 +177,8 @@ class TestOpenAICompatStreamFull:
         sse_lines.append(f"data: {json.dumps(final)}")
         sse_lines.append("data: [DONE]")
 
-        # Mock the httpx client stream context manager
-        mock_resp = MagicMock()
-        mock_resp.raise_for_status = MagicMock()
-        mock_resp.iter_lines.return_value = iter(sse_lines)
-
-        engine = _OpenAICompatibleEngine.__new__(_OpenAICompatibleEngine)
-        engine.engine_id = "test"
-        engine._host = "http://localhost:8000"
-        engine._api_prefix = "/v1"
-
-        mock_client = MagicMock()
-        mock_stream_ctx = MagicMock()
-        mock_stream_ctx.__enter__ = MagicMock(return_value=mock_resp)
-        mock_stream_ctx.__exit__ = MagicMock(return_value=False)
-        mock_client.stream.return_value = mock_stream_ctx
-        engine._client = mock_client
+        engine = VLLMEngine(host="http://localhost:8000")
+        engine._async_transport = _sse_transport(sse_lines)
 
         chunks = []
         async for chunk in engine.stream_full(
@@ -198,8 +197,6 @@ class TestOpenAICompatStreamFull:
 
     @pytest.mark.asyncio
     async def test_parses_tool_call_fragments(self):
-        from openjarvis.engine._openai_compat import _OpenAICompatibleEngine
-
         # Simulate streamed tool_call fragments
         _tc1 = (
             '{"choices": [{"delta": {"tool_calls": [{"index": 0, "id": "call_1",'
@@ -218,21 +215,8 @@ class TestOpenAICompatStreamFull:
             "data: [DONE]",
         ]
 
-        mock_resp = MagicMock()
-        mock_resp.raise_for_status = MagicMock()
-        mock_resp.iter_lines.return_value = iter(sse_lines)
-
-        engine = _OpenAICompatibleEngine.__new__(_OpenAICompatibleEngine)
-        engine.engine_id = "test"
-        engine._host = "http://localhost:8000"
-        engine._api_prefix = "/v1"
-
-        mock_client = MagicMock()
-        mock_stream_ctx = MagicMock()
-        mock_stream_ctx.__enter__ = MagicMock(return_value=mock_resp)
-        mock_stream_ctx.__exit__ = MagicMock(return_value=False)
-        mock_client.stream.return_value = mock_stream_ctx
-        engine._client = mock_client
+        engine = VLLMEngine(host="http://localhost:8000")
+        engine._async_transport = _sse_transport(sse_lines)
 
         chunks = []
         async for chunk in engine.stream_full(