diff --git a/run_agent.py b/run_agent.py
index 4b1429bc7..a3a2b6d58 100644
--- a/run_agent.py
+++ b/run_agent.py
@@ -31,6 +31,7 @@ logger = logging.getLogger(__name__)
 import os
 import random
 import re
+import ssl
 import sys
 import tempfile
 import time
@@ -10923,6 +10924,14 @@ class AIAgent:
                         and not isinstance(
                             api_error, (UnicodeEncodeError, json.JSONDecodeError)
                         )
+                        # ssl.SSLError (and its subclass SSLCertVerificationError)
+                        # inherits from OSError *and* ValueError via Python MRO,
+                        # so the isinstance(ValueError) check above would
+                        # misclassify a TLS transport failure as a local
+                        # programming bug and abort without retrying.  Exclude
+                        # ssl.SSLError explicitly so the error classifier's
+                        # retryable=True mapping takes effect instead.
+                        and not isinstance(api_error, ssl.SSLError)
                     )
                     is_client_error = (
                         is_local_validation_error