Requests GHA: Tests fail with ubuntu-20.04 (Fix)

The Fix

pip install requests==2.27.0

Based on closed psf/requests issue #5662 · 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

@@ -10,7 +10,7 @@ jobs:
       matrix:
         python-version: [2.7, 3.5, 3.6, 3.7, 3.8, 3.9]
-        os: [ubuntu-latest, macOS-latest, windows-latest]
+        os: [ubuntu-18.04, macOS-latest, windows-latest]
         include:

repro

Steps

verify

Follow the reproduction steps, confirm the failure, apply the fix, and repeat the same steps to verify the behavior changes.

fix.md

Option A — Upgrade to fixed release\npip install requests==2.27.0\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: GHA: Tests fail with ubuntu-20.04
Mechanism: Pins the GitHub Actions to Ubuntu 18.04 to avoid test failures on Ubuntu 20.04.
Why the fix works: Pins the GitHub Actions to Ubuntu 18.04 to avoid test failures on Ubuntu 20.04. (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

Production symptom (often without a traceback): GHA: Tests fail with ubuntu-20.04

Proof / Evidence

GitHub issue: #5662
Fix PR: https://github.com/psf/requests/pull/5663
First fixed release: 2.27.0
Reproduced locally: No (not executed)
Last verified: 2026-02-09
Confidence: 0.85
Did this fix it?: Yes (upstream fix exists)
Own content ratio: 0.69

Discussion

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

Jump to Sources Open on GitHub

“Good catch, @hugovk! It looks like our local httpbin server for tests is having trouble either with the newer version of openssl or configuration being…”

@nateprewitt · 2020-11-18 · confirmation · source

Failure Signature (Search String)

GHA: Tests fail with ubuntu-20.04
GitHub Actions fails when using the Ubuntu 20.04 image, and pass with 18.04.

Copy-friendly signature

signature.txt

Failure Signature
-----------------
GHA: Tests fail with ubuntu-20.04
GitHub Actions fails when using the Ubuntu 20.04 image, and pass with 18.04.

Error Message

Signature-only (no traceback captured)

error.txt

Error Message
-------------
GHA: Tests fail with ubuntu-20.04
GitHub Actions fails when using the Ubuntu 20.04 image, and pass with 18.04.

Minimal Reproduction

Steps

Fix Options (Details)

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

pip install requests==2.27.0

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/psf/requests/pull/5663

First fixed release: 2.27.0

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

Follow the reproduction steps, confirm the failure, apply the fix, and repeat the same steps to verify the behavior changes.

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.