diff --git a/agent/error_classifier.py b/agent/error_classifier.py
index 0cb397f3322..4d75502dab4 100644
--- a/agent/error_classifier.py
+++ b/agent/error_classifier.py
@@ -1043,6 +1043,17 @@ def _classify_by_status(
             )
         return result_fn(FailoverReason.overloaded, retryable=True)
 
+    # 408 Request Timeout — a transient timing failure the server itself flags
+    # as safe to retry (RFC 9110 §15.5.9), not a malformed request. Commonly
+    # emitted by reverse proxies sitting in front of self-hosted backends
+    # (llama.cpp / Ollama / vLLM) when a long generation outruns the proxy's
+    # request-read window. Route to the dedicated ``timeout`` reason (rebuild
+    # client + retry) instead of falling through to the generic 4xx bucket
+    # below, which would abort the turn on a retry-safe error the same way it
+    # aborts a 400 Bad Request.
+    if status_code == 408:
+        return result_fn(FailoverReason.timeout, retryable=True)
+
     # Other 4xx — non-retryable
     if 400 <= status_code < 500:
         return result_fn(
diff --git a/tests/agent/test_error_classifier.py b/tests/agent/test_error_classifier.py
index 3aff558062e..c336cc429a6 100644
--- a/tests/agent/test_error_classifier.py
+++ b/tests/agent/test_error_classifier.py
@@ -376,6 +376,26 @@ class TestClassifyApiError:
         result = classify_api_error(e)
         assert result.reason == FailoverReason.overloaded
 
+    def test_408_request_timeout_is_retryable_timeout(self):
+        """HTTP 408 Request Timeout is a transient timing failure the server
+        itself flags as safe to retry (RFC 9110 §15.5.9) — commonly emitted by
+        reverse proxies in front of self-hosted backends (llama.cpp / Ollama /
+        vLLM) when a long generation outruns the proxy's request-read window.
+        It must NOT fall into the generic 4xx bucket as a non-retryable
+        format_error, which would abort the turn on a retry-safe error."""
+        e = MockAPIError("Request Timeout", status_code=408)
+        result = classify_api_error(e, provider="vllm")
+        assert result.reason == FailoverReason.timeout
+        assert result.retryable is True
+
+    def test_400_bad_request_still_non_retryable_format_error(self):
+        """Guard the boundary: a genuine 400 Bad Request must remain a
+        non-retryable format_error and must not be swept up by the 408 branch."""
+        e = MockAPIError("Bad Request", status_code=400)
+        result = classify_api_error(e)
+        assert result.reason == FailoverReason.format_error
+        assert result.retryable is False
+
     def test_message_only_overloaded_without_status_is_overloaded(self):
         """Some Anthropic-compatible proxies surface 'overloaded' in the
         message with no 503/529 status_code. It must classify as overloaded