diff --git a/backend/app/api/helpers.py b/backend/app/api/helpers.py
index 8de9c40..5cdb1d7 100644
--- a/backend/app/api/helpers.py
+++ b/backend/app/api/helpers.py
@@ -184,9 +184,14 @@ def api_error_handler(err: ApiError):
 
 
 def internal_error(message: str, exc: BaseException, status: int = 500) -> ApiError:
-    """Log only the exception type; never expose exception text to clients."""
+    """Log the exception type and detail server-side; never expose text to clients.
+
+    The detail is what makes 500s diagnosable — without it the log says only
+    "LLMError" and the real cause (404 unknown model / 401 bad key / ...) is
+    lost. Client-facing text stays the generic message.
+    """
     current_app.logger.error(
-        "%s (error_type=%s)", message, type(exc).__name__
+        "%s (error_type=%s) %s", message, type(exc).__name__, exc
     )
     return ApiError(message, status)
 
diff --git a/backend/app/config.py b/backend/app/config.py
index dfd2f46..5a4da91 100644
--- a/backend/app/config.py
+++ b/backend/app/config.py
@@ -153,6 +153,14 @@ class Config:
 
     # LLM
     LLM_BASE_URL, LLM_MODEL, LLM_API_KEY, LLM_PROVIDER = resolve_llm()
+    # The local LLM server is shared (also serves Hermes): a concurrent long
+    # generation serializes requests, so a request can sit in the server queue
+    # well beyond a single attempt. Retry transient connection/timeout failures
+    # a few times so chat survives the queue instead of failing with 500.
+    LLM_MAX_ATTEMPTS = _get_int("LLM_MAX_ATTEMPTS", 3, minimum=1)
+    LLM_RETRY_DELAY_SECONDS = _get_float(
+        "LLM_RETRY_DELAY_SECONDS", 5.0, minimum=0.0
+    )
 
     # OAuth (Google + Facebook) — all optional; OAuth is disabled unless creds
     # are fully configured (fail closed). Client IDs / app IDs are public and
diff --git a/backend/app/llm.py b/backend/app/llm.py
index e8b45c8..348c45c 100644
--- a/backend/app/llm.py
+++ b/backend/app/llm.py
@@ -6,6 +6,7 @@ from __future__ import annotations
 
 import json
 import re
+import time
 from typing import Any
 
 from openai import OpenAI
@@ -55,8 +56,47 @@ class LLMClient:
             raise LLMError("LLM_API_KEY is not configured in .env")
         if not self.base_url:
             raise LLMError("LLM_BASE_URL is not configured (unknown provider)")
+        self.max_attempts = max(1, Config.LLM_MAX_ATTEMPTS)
+        self.retry_delay = Config.LLM_RETRY_DELAY_SECONDS
         self.client = OpenAI(base_url=self.base_url, api_key=self.api_key, timeout=180.0, max_retries=0)
 
+    def _create(self, *, model: str, temperature: float, max_tokens: int, messages, extra_body):
+        """Run chat.completions.create, retrying transient failures.
+
+        The local LLM server is shared (it also serves Hermes): a concurrent long
+        generation serializes requests, so a request can be dropped by a client
+        timeout or a connection reset while it is queued. Retry those transient
+        cases (openai.APIConnectionError — incl. APITimeoutError) up to
+        Config.LLM_MAX_ATTEMPTS times so chat survives the queue; a 4xx from the
+        server (bad key/model) is NOT transient and raises immediately.
+        """
+        import logging
+        from openai import APIConnectionError
+
+        logger = logging.getLogger(__name__)
+        for attempt in range(1, self.max_attempts + 1):
+            try:
+                return self.client.chat.completions.create(
+                    model=model,
+                    temperature=temperature,
+                    max_tokens=max_tokens,
+                    messages=messages,
+                    extra_body=extra_body,
+                )
+            except APIConnectionError as exc:
+                if attempt == self.max_attempts:
+                    raise
+                logger.warning(
+                    "LLM attempt %d/%d failed (%s); retrying in %.1fs",
+                    attempt,
+                    self.max_attempts,
+                    exc,
+                    self.retry_delay,
+                )
+                time.sleep(self.retry_delay)
+        # Unreachable: the loop either returns a response or raises.
+        raise LLMError("LLM call failed after retries")
+
     def complete(
         self,
         system_prompt: str,
@@ -72,7 +112,7 @@ class LLMClient:
             # (measured 313s -> 44s per persona on the local tabbyAPI server).
             extra_body = {"enable_thinking": False}
         try:
-            resp = self.client.chat.completions.create(
+            resp = self._create(
                 model=self.model,
                 temperature=temperature,
                 max_tokens=max_tokens,
@@ -141,11 +181,12 @@ class LLMClient:
                 mapped = "user"
             api_messages.append({"role": mapped, "content": m.get("text") or m.get("content") or ""})
         try:
-            resp = self.client.chat.completions.create(
+            resp = self._create(
                 model=self.model,
                 temperature=temperature,
                 max_tokens=max_tokens,
                 messages=api_messages,
+                extra_body=None,
             )
         except Exception as exc:
             raise LLMError(f"LLM call failed: {exc}") from exc
diff --git a/backend/tests/test_internal_error_logging.py b/backend/tests/test_internal_error_logging.py
new file mode 100644
index 0000000..5bc26c7
--- /dev/null
+++ b/backend/tests/test_internal_error_logging.py
@@ -0,0 +1,60 @@
+"""internal_error: server log must carry the exception detail for 500 diagnosis,
+while the client only ever sees the generic message.
+
+Uses a handler attached directly to the app logger so the assertion is
+independent of suite-wide logging configuration (other tests may set levels
+or propagation flags on shared loggers).
+"""
+from __future__ import annotations
+
+import logging
+
+import pytest
+
+from app.api.helpers import internal_error
+
+
+class _Capture(logging.Handler):
+    def __init__(self):
+        super().__init__(level=logging.ERROR)
+        self.messages: list[str] = []
+
+    def emit(self, record: logging.LogRecord):
+        self.messages.append(record.getMessage())
+
+
+@pytest.fixture()
+def captured_logs(app):
+    handler = _Capture()
+    app.logger.addHandler(handler)
+    # Other tests (alembic migrations in test_db_schema) run logging.config
+    # with disable_existing_loggers=True, which disables the app logger.
+    # Restore it so this assertion is independent of test order.
+    app.logger.disabled = False
+    yield handler
+    app.logger.removeHandler(handler)
+
+
+def test_internal_error_logs_detail_and_hides_it_from_client(app, captured_logs):
+    sentinel = "404 model 'qwen3.8' not found on this endpoint"
+    with app.app_context():
+        err = internal_error("LLM service unavailable", ValueError(sentinel))
+
+    # Client-facing payload stays generic — the sentinel must not leak.
+    assert err.message == "LLM service unavailable"
+    assert err.status == 500
+    assert sentinel not in err.message
+
+    # Server-side log DOES carry the detail, so a 500 is diagnosable.
+    logged = " ".join(captured_logs.messages)
+    assert "LLM service unavailable" in logged
+    assert "ValueError" in logged
+    assert sentinel in logged
+
+
+def test_internal_error_default_status_and_type(app, captured_logs):
+    with app.app_context():
+        err = internal_error("boom", RuntimeError("disk full"))
+    assert err.status == 500
+    logged = " ".join(captured_logs.messages)
+    assert "RuntimeError" in logged and "disk full" in logged
diff --git a/backend/tests/test_llm_retry_queue.py b/backend/tests/test_llm_retry_queue.py
new file mode 100644
index 0000000..8cd8204
--- /dev/null
+++ b/backend/tests/test_llm_retry_queue.py
@@ -0,0 +1,95 @@
+"""LLM client: transient failures (timeout / connection reset — what a shared,
+queueing LLM server produces under load) are retried so chat survives the queue;
+a 4xx from the server (bad key / model) is NOT retried and fails fast.
+"""
+from __future__ import annotations
+
+import httpx
+import pytest
+
+from app.llm import LLMClient, LLMError
+from openai import APIStatusError, APITimeoutError
+
+
+def _make_client(max_attempts: int = 3) -> LLMClient:
+    c = LLMClient(base_url="http://localhost:9/v1", api_key="test-key", model="m")
+    c.max_attempts = max_attempts
+    c.retry_delay = 0.0
+    return c
+
+
+def _resp():
+    message = type("M", (), {"content": "ok"})()
+    choice = type("C", (), {"message": message})()
+    return type("R", (), {"choices": [choice]})()
+
+
+def _patch_sleep(monkeypatch):
+    import app.llm as llm
+
+    monkeypatch.setattr(llm.time, "sleep", lambda s: None)
+
+
+def test_transient_failure_retries_then_succeeds(monkeypatch):
+    c = _make_client(max_attempts=3)
+    _patch_sleep(monkeypatch)
+    calls = {"n": 0}
+
+    def flaky(**kwargs):
+        calls["n"] += 1
+        if calls["n"] < 3:
+            raise APITimeoutError(request="req")
+        return _resp()
+
+    c.client.chat.completions.create = flaky
+    assert c.complete("sys", "user") == "ok"
+    assert calls["n"] == 3
+
+
+def test_persistent_transient_failure_raises_after_max_attempts(monkeypatch):
+    c = _make_client(max_attempts=3)
+    _patch_sleep(monkeypatch)
+    calls = {"n": 0}
+
+    def always_timeout(**kwargs):
+        calls["n"] += 1
+        raise APITimeoutError(request="req")
+
+    c.client.chat.completions.create = always_timeout
+    with pytest.raises(LLMError):
+        c.complete("sys", "user")
+    assert calls["n"] == 3
+
+
+def test_4xx_not_retried_fails_fast(monkeypatch):
+    c = _make_client(max_attempts=3)
+    _patch_sleep(monkeypatch)
+    calls = {"n": 0}
+
+    def bad_model(**kwargs):
+        calls["n"] += 1
+        raise APIStatusError(
+            message="model not found",
+            response=httpx.Response(404, request="req"),
+            body=None,
+        )
+
+    c.client.chat.completions.create = bad_model
+    with pytest.raises(LLMError):
+        c.complete("sys", "user")
+    # A 4xx is not transient: exactly one attempt, no retry.
+    assert calls["n"] == 1
+
+
+def test_success_no_retry(monkeypatch):
+    c = _make_client(max_attempts=3)
+    _patch_sleep(monkeypatch)
+    calls = {"n": 0}
+
+    def ok(**kwargs):
+        calls["n"] += 1
+        return _resp()
+
+    c.client.chat.completions.create = ok
+    assert c.complete("sys", "user") == "ok"
+    assert calls["n"] == 1