urllib3 PyOpenSSL: Fails to import after installation with

The Fix

pip install urllib3==1.25

Based on closed urllib3/urllib3 issue #839 · 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

@@ -40,7 +40,8 @@
       packages=['urllib3',
                 'urllib3.packages', 'urllib3.packages.ssl_match_hostname',
-                'urllib3.contrib', 'urllib3.util',
+                'urllib3.packages.backports', 'urllib3.contrib',
+                'urllib3.util',

repro.py

Traceback (most recent call last):
  File "/Users/davidf/Projects/webcrystal/venv/lib/python3.4/site-packages/urllib3/contrib/pyopenssl.py", line 60, in <module>
    from socket import _fileobject
ImportError: cannot import name '_fileobject'

During handling of the above exception, another exception occurred:

Traceback (most recent call last):
  File "<stdin>", line 1, in <module>
  File "/Users/davidf/Projects/webcrystal/venv/lib/python3.4/site-packages/urllib3/contrib/pyopenssl.py", line 63, in <module>
    from urllib3.packages.backports.makefile import backport_makefile
ImportError: No module named 'urllib3.packages.backports'

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==1.25\nWhen NOT to use: This fix should not be applied if the package structure is altered in future versions.\n\n

Why This Fix Works in Production

Trigger: from socket import _fileobject
Mechanism: The package was incorrectly configured, missing the backports module in the setup
Why the fix works: The issue was resolved by ensuring that backports are distributed correctly in the package setup. (first fixed release: 1.25).

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

Shows up under Python 3.4.4 in real deployments (not just unit tests).
The package was incorrectly configured, missing the backports module in the setup
Surfaces as: Traceback (most recent call last):

Proof / Evidence

GitHub issue: #839
Fix PR: https://github.com/urllib3/urllib3/pull/841
First fixed release: 1.25
Reproduced locally: No (not executed)
Last verified: 2026-02-09
Confidence: 0.85
Did this fix it?: Yes (upstream fix exists)
Own content ratio: 0.43

Discussion

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

Jump to Sources Open on GitHub

“Nope, that looks like a real bug to me! In particular, this looks like we incorrectly packaged the release”

@Lukasa · 2016-04-11 · source

Failure Signature (Search String)

from socket import _fileobject

Error Message

Stack trace

error.txt

Error Message
-------------
Traceback (most recent call last):
  File "/Users/davidf/Projects/webcrystal/venv/lib/python3.4/site-packages/urllib3/contrib/pyopenssl.py", line 60, in <module>
    from socket import _fileobject
ImportError: cannot import name '_fileobject'

During handling of the above exception, another exception occurred:

Traceback (most recent call last):
  File "<stdin>", line 1, in <module>
  File "/Users/davidf/Projects/webcrystal/venv/lib/python3.4/site-packages/urllib3/contrib/pyopenssl.py", line 63, in <module>
    from urllib3.packages.backports.makefile import backport_makefile
ImportError: No module named 'urllib3.packages.backports'

Minimal Reproduction

repro.py

Traceback (most recent call last):
  File "/Users/davidf/Projects/webcrystal/venv/lib/python3.4/site-packages/urllib3/contrib/pyopenssl.py", line 60, in <module>
    from socket import _fileobject
ImportError: cannot import name '_fileobject'

During handling of the above exception, another exception occurred:

Traceback (most recent call last):
  File "<stdin>", line 1, in <module>
  File "/Users/davidf/Projects/webcrystal/venv/lib/python3.4/site-packages/urllib3/contrib/pyopenssl.py", line 63, in <module>
    from urllib3.packages.backports.makefile import backport_makefile
ImportError: No module named 'urllib3.packages.backports'

Environment

Python: 3.4.4

Why It Broke

The package was incorrectly configured, missing the backports module in the setup

Fix Options (Details)

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

pip install urllib3==1.25

When NOT to use: This fix should not be applied if the package structure is altered in future versions.

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/841

First fixed release: 1.25

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

When NOT to Use This Fix

This fix should not be applied if the package structure is altered in future versions.

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
1.25	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.

urllib3 PyOpenSSL: Fails to import after installation with the provided instructions (Fix)