Add debug logging for retry behavior diagnostics

Author: brandonkachen

cli/src/hooks/use-send-message.ts

@@ -2004,6 +2004,20 @@ export const useSendMessage = ({
         const shouldRetryError =
           timedOutDueToSdk || !isConnectedRef.current || isRetryableError(error)
 
+        // Debug: Log what's triggering retry
+        if (shouldRetryError) {
+          logger.warn(
+            {
+              userMessageId,
+              errorMessage,
+              timedOutDueToSdk,
+              isConnected: isConnectedRef.current,
+              isRetryableError: isRetryableError(error),
+            },
+            '[RETRY-DEBUG] Error detected as retryable - will retry',
+          )
+        }
+
         // Only mark as interrupted and show error if NOT retrying
         // (retryable errors will be retried silently)
         if (!shouldRetryError) {