getsentry · cursor · Apr 23, 2026
@@ -11,6 +11,9 @@
 from sentry_sdk.envelope import Envelope
 from sentry_sdk.utils import format_timestamp
 
+ENVELOPE_UPLOAD_MAX_ATTEMPTS = 3
+ENVELOPE_UPLOAD_TIMEOUT_SECONDS = 10
+
 
 class GithubSentryError(Exception):
     pass
@@ -128,13 +131,35 @@ def _send_envelope(self, trace):
         with gzip.GzipFile(fileobj=body, mode="w") as f:
             envelope.serialize_into(f)
 
-        req = requests.post(
-            self.sentry_project_url,
-            data=body.getvalue(),
-            headers=headers,
-        )
-        req.raise_for_status()
-        return req
+        for attempt in range(1, ENVELOPE_UPLOAD_MAX_ATTEMPTS + 1):
+            try:
+                req = requests.post(
+                    self.sentry_project_url,
+                    data=body.getvalue(),
+                    headers=headers,
+                    timeout=ENVELOPE_UPLOAD_TIMEOUT_SECONDS,
+                )
+                req.raise_for_status()
+                return req
+            except (
+                requests.exceptions.ConnectionError,
+                requests.exceptions.SSLError,
+                requests.exceptions.Timeout,
+            ) as err:
+                if attempt == ENVELOPE_UPLOAD_MAX_ATTEMPTS:
+                    logging.warning(
+                        "Failed sending Sentry envelope after %s attempts: %s",
+                        ENVELOPE_UPLOAD_MAX_ATTEMPTS,
+                        err,
+                    )
+                    return
+                logging.info(
+                    "Retrying Sentry envelope upload after transient network error "
+                    "(attempt %s/%s): %s",
+                    attempt,
+                    ENVELOPE_UPLOAD_MAX_ATTEMPTS,
+                    err,
+                )
 
     def send_trace(self, job):
         # This can happen when the workflow is skipped and there are no steps

@@ -1,7 +1,9 @@
 from __future__ import annotations
 
+import logging
 import sys
 from datetime import datetime
+from unittest.mock import Mock
 from unittest.mock import patch
 
 import pytest
@@ -11,6 +13,8 @@
 from requests import HTTPError
 from sentry_sdk.utils import format_timestamp
 
+from src.github_sdk import ENVELOPE_UPLOAD_MAX_ATTEMPTS
+from src.github_sdk import ENVELOPE_UPLOAD_TIMEOUT_SECONDS
 from src.github_sdk import GithubClient
 
 DSN = "https://foo@random.ingest.sentry.io/bar"
@@ -158,3 +162,53 @@ def test_send_trace(
     #     resp.request.body
     #     == b"\x1f\x8b\x08\x00\xf1\x16}b\x02\xff\xb5TM\x8f\xd30\x10\xbd\xef\xaf\x88|\x02\xa9m\x1c\xc7\x89\x93H\x08\xd0\x8a;\x12\x9c@\xa8\x9a\xd8\xe3&\xbb\xf9\"vX\xaa\xaa\xff\x1d{\xdb\xee\x97\x96n\xcb\x8aS\xd3\x99\xf1\xf8\xbd7o\xbc\xd9^l\x88]\x0fH\nbG\xe8\x0cH[\xf7\x1d\x99\x11\xd9w\x16;\xbb\xdc'a\x18\x9aZ\x82O\x86W\xe6\xb6\xa2\xc1ne+RD\x19\xa7\xbe\r\xfe\xf2\xf5\xb5r\xd5\t \x139H\x95g\x8c\xcbRC\x96P\xceh\x14K]\xea\xac\x14\xee\xf4\xb3\x97>\xfcW\x10=\xdebP\x81EcM\xf0\x86\xbe=\xe0\xfam\r)6\xbe\\\xa2\xff0\x03t\xbb\x9b\x81\xd3He\xb1\x14()\xcf\x13\xbdk*q\x97\xcd\xa2\x92\x96\x08)\xa0\xd2<\x8b\x04\x08\xaeb\xa6\x04Ms\x9a)\xcd\x1e\xe1r\xadgD\x81\x05\x7f\xc3U_\xbahe\xed`\x8a0\\\xd5\xb6\x9a\xca\x85\xec\xdbp\x85\xd68\xde\xe3:\xdc\xff\x8cSg\xc2$KD\xc2\x04O\xe8{Y\xa1\xbc^\x9a\xa9\xb6\xb8\xd4\xbd\x9c\xcc;;N\xbe\xf50\x9e\xd8q\x98\x9a&\x8c\xe3\x98\x0b\xb2\x9d\x91~\xf8\x9b4\n\x8d\x1c\xeb\xe1\x98z\xc6\x82\x9d\x9cv\xa4\xbf&[\xd7l28zz\x1d\xb4\x9e\xf5\xc7\xaaE\x15|\xb2\xa8\xd7\xae\x18[\xa8\x1b\xaf\xa9\x8f.\xd0G#\xf6a\xe5\xa3\x1e\xa8\x07\xe3\xfa\x8d\xce#u\xeb\xee\x80\xd6#c\x94\xb19\xe5s\x9a~\x8d\xf2\"aE$\xbeyY\x9f/a\xb4\xa0I\x11\xefJ`e\xf6R/\xefp\x9aIJ4\xc6\xa5K\xe7\rY\x1d\xe0\x84\xa0\xd4\xdc\xa1\xae\xbb\xd5\xbc\x81\xb5c\xe1\xad\xd1\xb6\xb5\xf5\xd4U.R\x16e\x90s\x95\x01\x95\x8aQ\xe7\x88(B\x10\xaa\xc44\x93\x89\x88Qs\xe5\xce\x8c8\xf4\xee\xc4S\xcd}f\xea\x96`-\xb6\x83k\x19\xcd\xc8M?^\xeb\xa6\xbf\xf1\x08\x1c\xa6\xc1:8\xb8X\xb7\x8d\x1f\xa5\x9b\xd0r\xc4\x9f\x93\xe3H\x8a\xdbQyq\x9c+\x1d\x87\xef\x9b\xdd\xcc\xbe\xa0\r\xa6!\xf0N\x9a\x1d\x04\x7f\x14\x1b`\xf4\x1bt\xd4\xcc\xf7I*X\xaaK\x0e,\xe6\x11\x17B\x92\xd3\xa6\x91.(\xa5G&\xb2+c\xf4\xae\xec\x8c\xed\xd9\xce\xf6T?;=\x82U%\xc7E\xdd?\xf0\xf3n\xb3\xe7\x95m\x9b\xb9\xed\xe7u\x0b+,\x1a\xf0\x06\xbd\x97\xe4\x9f\xce\x9e'\x1d\x08!RT\x11S\x00\x9c\xe7\xe5i\xd2=\xd0\xe4XY\x92\xbdN\xba\xde\xd8\xe0\xd2\xbf\x19\xfdd\x83;7\x1e\xc4y>{\x1e\xfd\x14\x9da\xb4\x8e\x05\xd39\xcf3x\x89\xfeaI_\xa0\xbf/K^E\xff\xb2o\x87\xc6=5\x8f\xd7\xe4I\xf4<\xba\x8e\xa2\xdbWT\x98\xe8\x88\xbb\xa7\xe1D\xba\xc9\xff\xa4\xfbc{\xf1\x07Hk>,{\x07\x00\x00"
     # )
+
+
+@responses.activate
+@patch("src.github_sdk.requests.post")
+def test_send_trace_retries_transient_upload_errors(
+    mock_post,
+    jobA_job,
+    jobA_runs,
+    jobA_workflow,
+):
+    responses.get(jobA_job["run_url"], json=jobA_runs)
+    responses.get(jobA_runs["workflow_url"], json=jobA_workflow)
+
+    success_response = Mock()
+    success_response.raise_for_status.return_value = None
+    mock_post.side_effect = [
+        requests.exceptions.SSLError("transient handshake failure"),
+        success_response,
+    ]
+
+    client = GithubClient(dsn=DSN, token=TOKEN)
+    response = client.send_trace(jobA_job)
+
+    assert response is success_response
+    assert mock_post.call_count == 2
+    for call in mock_post.call_args_list:
+        assert call.kwargs["timeout"] == ENVELOPE_UPLOAD_TIMEOUT_SECONDS
+
+
+@responses.activate
+@patch("src.github_sdk.requests.post")
+def test_send_trace_returns_none_when_retries_exhausted(
+    mock_post,
+    caplog,
+    jobA_job,
+    jobA_runs,
+    jobA_workflow,
+):
+    responses.get(jobA_job["run_url"], json=jobA_runs)
+    responses.get(jobA_runs["workflow_url"], json=jobA_workflow)
+
+    mock_post.side_effect = requests.exceptions.SSLError("still failing")
+    client = GithubClient(dsn=DSN, token=TOKEN)
+
+    with caplog.at_level(logging.WARNING):
+        response = client.send_trace(jobA_job)
+
+    assert response is None
+    assert mock_post.call_count == ENVELOPE_UPLOAD_MAX_ATTEMPTS
+    assert "Failed sending Sentry envelope after" in caplog.text