From e25b158218aa37e6a782d11fb37476c02f254221 Mon Sep 17 00:00:00 2001
From: Aran Yogesh <yogesh.mahendran@langchain.dev>
Date: Tue, 7 Apr 2026 17:57:21 -0700
Subject: [PATCH] fix: add retry with delay for sandbox proxy config to avoid
 500 when proxy isn't ready (#1168)

* fix: add retry with delay for sandbox proxy config to avoid 500 when proxy isn't ready

* fix: add retry with exponential backoff and connection error handling for proxy config
---
 agent/integrations/langsmith.py | 38 +++++++++++++++++++++++++++------
 1 file changed, 32 insertions(+), 6 deletions(-)

diff --git a/agent/integrations/langsmith.py b/agent/integrations/langsmith.py
index 9324be2a..d031c7e6 100644
--- a/agent/integrations/langsmith.py
+++ b/agent/integrations/langsmith.py
@@ -69,13 +69,39 @@ def _configure_github_proxy(sandbox_name: str, github_token: str) -> None:
             ]
         }
     }
+    max_retries = 3
+    retry_delay = 5
     with httpx.Client() as client:
-        response = client.patch(
-            url,
-            json=payload,
-            headers={"X-API-Key": api_key},
-        )
-        response.raise_for_status()
+        for attempt in range(max_retries):
+            if attempt > 0:
+                time.sleep(retry_delay)
+            try:
+                response = client.patch(
+                    url,
+                    json=payload,
+                    headers={"X-API-Key": api_key},
+                )
+            except httpx.HTTPError as e:
+                logger.warning(
+                    "Proxy config attempt %d/%d connection error: %s",
+                    attempt + 1,
+                    max_retries,
+                    e,
+                )
+                if attempt == max_retries - 1:
+                    raise
+                continue
+            if response.is_success:
+                break
+            logger.warning(
+                "Proxy config attempt %d/%d failed (%s): %s",
+                attempt + 1,
+                max_retries,
+                response.status_code,
+                response.text,
+            )
+            if attempt == max_retries - 1:
+                response.raise_for_status()
     logger.info("Configured GitHub proxy for sandbox %s", sandbox_name)