Requests security extras need to be updated (Fix)

The Fix

pip install requests==2.27.0

Based on closed psf/requests issue #3689 · 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%.

Open PR/Commit

@@ -94,7 +94,8 @@ def run_tests(self):
     tests_require=test_requirements,
     extras_require={
-        'security': ['pyOpenSSL>=0.13', 'ndg-httpsclient', 'pyasn1'],
+        'security': ['pyOpenSSL>=0.14', 'cryptography>=1.3.4', 'idna>=2.0.0'],
         'socks': ['PySocks>=1.5.6, !=1.5.7'],

fix.md

Option A — Upgrade to fixed release\npip install requests==2.27.0\nWhen NOT to use: This fix is not applicable if the application relies on deprecated dependencies.\n\n

Why This Fix Works in Production

Trigger: Users experience import errors when trying to use security features in requests.
Mechanism: Older versions of pyOpenSSL cause import errors when installing requests with security extras
Why the fix works: Updated the security extras in setup.py to replace deprecated dependencies with required ones. (first fixed release: 2.27.0).

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

Older versions of pyOpenSSL cause import errors when installing requests with security extras
Production symptom (often without a traceback): Users experience import errors when trying to use security features in requests.

Proof / Evidence

GitHub issue: #3689
Fix PR: https://github.com/psf/requests/pull/3693
First fixed release: 2.27.0
Reproduced locally: No (not executed)
Last verified: 2026-02-07
Confidence: 0.95
Did this fix it?: Yes (upstream fix exists)
Own content ratio: 0.72

Discussion

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

Jump to Sources Open on GitHub

“Given that we're shipping a patch release, I may just fix this myself and ship it today.”

@Lukasa · 2016-11-16 · source

Failure Signature (Search String)

Users experience import errors when trying to use security features in requests.

Copy-friendly signature

signature.txt

Failure Signature
-----------------
Users experience import errors when trying to use security features in requests.

Error Message

Signature-only (no traceback captured)

error.txt

Error Message
-------------
Users experience import errors when trying to use security features in requests.

What Broke

Users experience import errors when trying to use security features in requests.

Why It Broke

Older versions of pyOpenSSL cause import errors when installing requests with security extras

Fix Options (Details)

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

pip install requests==2.27.0

When NOT to use: This fix is not applicable if the application relies on deprecated dependencies.

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

Fix reference: https://github.com/psf/requests/pull/3693

First fixed release: 2.27.0

Last verified: 2026-02-07. Validate in your environment.

When NOT to Use This Fix

This fix is not applicable if the application relies on deprecated dependencies.

Did This Fix Work in Your Case?

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

Prevention

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
2.27.0	Fixed

Related Issues

No related fixes found.

Cluster: requests:configuration-error Requests hub Requests 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.