diff --git a/run_agent.py b/run_agent.py
index eaafac5b43f78..0aa18f11024b2 100644
--- a/run_agent.py
+++ b/run_agent.py
@@ -31,6 +31,7 @@
 import os
 import random
 import re
+import ssl
 import sys
 import tempfile
 import time
@@ -10680,7 +10681,7 @@ def _stop_spinner():
                     # errors (ValueError, TypeError) are programming bugs.
                     is_local_validation_error = (
                         isinstance(api_error, (ValueError, TypeError))
-                        and not isinstance(api_error, UnicodeEncodeError)
+                        and not isinstance(api_error, (UnicodeEncodeError, ssl.SSLError))  # ssl.SSLError subclasses ValueError via OSError — transport error, not a programming bug
                     )
                     is_client_error = (
                         is_local_validation_error
diff --git a/tests/run_agent/test_14367_ssl_local_validation.py b/tests/run_agent/test_14367_ssl_local_validation.py
new file mode 100644
index 0000000000000..e76031666e297
--- /dev/null
+++ b/tests/run_agent/test_14367_ssl_local_validation.py
@@ -0,0 +1,77 @@
+"""Tests for #14367 — ssl.SSLCertVerificationError mis-classified as local validation error.
+
+ssl.SSLCertVerificationError inherits from SSLError → OSError → ValueError.
+The is_local_validation_error guard in run_agent.py caught it via isinstance(e, ValueError)
+and triggered a non-retryable abort, even though the error classifier returns retryable=True
+for all OSError subclasses (transport heuristic, step 7).
+
+Fix: add ssl.SSLError to the exclusion tuple alongside UnicodeEncodeError.
+"""
+
+import ssl
+
+
+# ── Helper: replicate the fixed guard from run_agent.py ───────────────────
+
+def _is_local_validation_error(api_error: BaseException) -> bool:
+    """Mirror of the is_local_validation_error check in run_agent.py."""
+    return (
+        isinstance(api_error, (ValueError, TypeError))
+        and not isinstance(api_error, (UnicodeEncodeError, ssl.SSLError))
+    )
+
+
+# ── Tests ──────────────────────────────────────────────────────────────────
+
+class TestSSLErrorNotLocalValidation:
+    """ssl.SSLError and its subclasses must not be treated as local
+    validation errors — they are transport errors and should be retried."""
+
+    def test_ssl_cert_verification_error_is_not_local(self):
+        """SSLCertVerificationError (the reported bug case) should not be
+        classified as a local validation error."""
+        e = ssl.SSLCertVerificationError("certificate verify failed: self-signed certificate")
+        assert not _is_local_validation_error(e)
+
+    def test_ssl_error_base_is_not_local(self):
+        """ssl.SSLError itself (parent of all SSL errors) should not be
+        classified as a local validation error."""
+        e = ssl.SSLError("unknown SSL error")
+        assert not _is_local_validation_error(e)
+
+    def test_ssl_cert_verification_error_is_value_error_via_mro(self):
+        """Confirm the MRO bug exists: SSLCertVerificationError IS a ValueError,
+        which is why the pre-fix guard misfired."""
+        e = ssl.SSLCertVerificationError("cert error")
+        assert isinstance(e, ValueError), (
+            "Prerequisite: SSLCertVerificationError must subclass ValueError via MRO"
+        )
+
+
+class TestExistingExclusionsPreserved:
+    """Existing exclusions (UnicodeEncodeError) must remain effective."""
+
+    def test_unicode_encode_error_is_not_local(self):
+        """Pre-existing: UnicodeEncodeError should not be a local validation error."""
+        e = UnicodeEncodeError("utf-8", "x", 0, 1, "invalid char")
+        assert not _is_local_validation_error(e)
+
+
+class TestValueErrorAndTypeErrorStillLocal:
+    """Plain ValueError and TypeError remain local validation errors — the fix
+    must not weaken detection of real programming bugs."""
+
+    def test_plain_value_error_is_local(self):
+        e = ValueError("unexpected keyword argument 'stream_options'")
+        assert _is_local_validation_error(e)
+
+    def test_plain_type_error_is_local(self):
+        e = TypeError("got an unexpected keyword argument 'stream_options'")
+        assert _is_local_validation_error(e)
+
+    def test_json_decode_error_is_still_local(self):
+        """json.JSONDecodeError is a ValueError subclass — still local until
+        #14366 lands its own exclusion."""
+        import json
+        e = json.JSONDecodeError("Expecting value", "doc", 0)
+        assert _is_local_validation_error(e)