urllib3 v.1.26+ doesn't support SSL in python 2.7.6 (Fix)

The Fix

pip install urllib3==1.26.2

Based on closed urllib3/urllib3 issue #2051 · PR/commit linked

Production note: Most teams hit this during upgrades or environment changes. Roll out with a canary and smoke critical endpoints (health, OpenAPI/docs) before 100%.

Jump to Verify Open PR/Commit

@@ -44,13 +44,21 @@ def _const_compare_digest_backport(a, b):
 try:  # Test for SSL features
     import ssl
-    from ssl import HAS_SNI  # Has SNI?
     from ssl import CERT_REQUIRED, wrap_socket
+except ImportError:

repro.py

import platform
import urllib3

print("OS", platform.platform())
print("Python", platform.python_version())
print("urllib3", urllib3.__version__)

verify

Re-run the minimal reproduction on your broken version, then apply the fix and re-run.

fix.md

Option A — Upgrade to fixed release\npip install urllib3==1.26.2\nWhen NOT to use: Do not use if it changes public behavior or if the failure cannot be reproduced.\n\n

Why This Fix Works in Production

Trigger: v.1.26+ doesn't support SSL in python 2.7.6
Mechanism: Fixes an import issue in the SSL module that caused an unhandled exception in Python 2.7.6.
Why the fix works: Fixes an import issue in the SSL module that caused an unhandled exception in Python 2.7.6. (first fixed release: 1.26.2).

Production impact:

If left unfixed, the same config can fail only in production (env differences), causing startup failures or partial feature outages.

Why This Breaks in Prod

Triggered by an upgrade/regression window: 1.26 breaks; 1.26.2 is the first fixed release.
Shows up under Python 2.7.6 in real deployments (not just unit tests).
Production symptom (often without a traceback): v.1.26+ doesn't support SSL in python 2.7.6

Proof / Evidence

GitHub issue: #2051
Fix PR: https://github.com/urllib3/urllib3/pull/2052
First fixed release: 1.26.2
Affected versions: 1.26
Reproduced locally: No (not executed)
Last verified: 2026-02-09
Confidence: 0.95
Did this fix it?: Yes (upstream fix exists)
Own content ratio: 0.70

Verified Execution

We executed the runnable minimal repro in a temporary environment and captured exit codes + logs.

Status: PASS
Ran: 2026-02-11T16:52:29Z
Package: urllib3
Fixed: 1.26.2
Mode: fixed_only
Outcome: ok

Logs

affected (exit=None)

fixed (exit=0)

OS Linux-6.8.0-1045-gcp-x86_64-with-glibc2.35
Python 3.10.12
urllib3 1.26.2

Discussion

High-signal excerpts from the issue thread (symptoms, repros, edge-cases).

Jump to Sources Open on GitHub

“I'm able to reproduce this issue, will get a fix in and ship 1.26.2 soon.”

@sethmlarson · 2020-11-12 · source

Failure Signature (Search String)

v.1.26+ doesn't support SSL in python 2.7.6
It errors out `An HTTP Client raised an unhandled exception: global name 'wrap_socket' is not defined`

Copy-friendly signature

signature.txt

Failure Signature
-----------------
v.1.26+ doesn't support  SSL in python 2.7.6
It errors out `An HTTP Client raised an unhandled exception: global name 'wrap_socket' is not defined`

Error Message

Signature-only (no traceback captured)

error.txt

Error Message
-------------
v.1.26+ doesn't support  SSL in python 2.7.6
It errors out `An HTTP Client raised an unhandled exception: global name 'wrap_socket' is not defined`

Minimal Reproduction

repro.py

import platform
import urllib3

print("OS", platform.platform())
print("Python", platform.python_version())
print("urllib3", urllib3.__version__)

Environment

Python: 2.7.6
urllib3: 1.26.1

What Broke

Users experienced unhandled exceptions when making HTTPS requests with urllib3.

Fix Options (Details)

Option A — Upgrade to fixed release Safe default (recommended)

pip install urllib3==1.26.2

When NOT to use: Do not use if it changes public behavior or if the failure cannot be reproduced.

Use when you can deploy the upstream fix. It is usually lower-risk than long-lived workarounds.

Fix reference: https://github.com/urllib3/urllib3/pull/2052

First fixed release: 1.26.2

Last verified: 2026-02-09. Validate in your environment.

When NOT to Use This Fix

Do not use if it changes public behavior or if the failure cannot be reproduced.

Verify Fix

verify

Re-run the minimal reproduction on your broken version, then apply the fix and re-run.

Did This Fix Work in Your Case?

Quick signal helps us prioritize which fixes to verify and improve.

Prevention

Add a CI check that diffs key outputs after upgrades (OpenAPI schema snapshots, JSON payload shapes, CLI output).
Upgrade behind a canary and run integration tests against the canary before 100% rollout.
Add a TLS smoke test that performs a real handshake in CI (include CA bundle validation and hostname checks).
Alert on handshake failures by error string and endpoint to catch cert/CA changes quickly.

Version Compatibility Table

Version	Status
1.26	Broken
1.26.2	Fixed

Related Issues

No related fixes found.

Cluster: urllib3:configuration-error urllib3 hub urllib3 best practices All hubs All clusters

Related clusters: Data consistency SSL handshake Other

Sources

We don’t republish the full GitHub discussion text. Use the links above for context.