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The Fix

pip install requests==2.27.0

Based on closed psf/requests issue #5214 · 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
@@ -103,7 +103,7 @@ Requests officially supports Python 2.7 & 3.4–3.8. ------------------------------------- -## P.S. — Documentation is Available at [`//2.python-requests.org`](https://2.python-requests.org/). +## P.S. — Documentation is Available at [`//requests.readthedocs.io`](https://requests.readthedocs.io/en/master/).
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: This fix should not be used if the documentation is still hosted at the old URL.\n\n

Why This Fix Works in Production

  • Trigger: Looks like www.python-requests.org and docs.python-requests.org are redirecting to https://2.python-requests.org and failing SSL negotiation, making the site…
  • Mechanism: The documentation link in the README was pointing to an outdated URL that failed SSL negotiation
  • Why the fix works: Fixed the documentation link in the README to point to the correct URL. (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

  • The documentation link in the README was pointing to an outdated URL that failed SSL negotiation
  • Production symptom (often without a traceback): Looks like www.python-requests.org and docs.python-requests.org are redirecting to https://2.python-requests.org and failing SSL negotiation, making the site appear down. Google links are all dead, documentation links don't work, etc.

Proof / Evidence

  • GitHub issue: #5214
  • Fix PR: https://github.com/psf/requests/pull/5216
  • 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: 0.67

Discussion

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

“This should be resolved now with #5236. Thanks everyone!”
@nateprewitt · 2019-10-25 · confirmation · source
“My first Google result is 2.python-requests.org, which is down. Came here to report this.”
@CarlosDomingues · 2019-09-26 · source
“Chiming in here vs”
@nicktimko · 2019-11-08 · source
“With (I believe) the same root cause, the search functionality on all (working) versions of the docs (eg https://requests.readthedocs.io/en/master/, https://requests.kennethreitz.org/en/master/) is broken, as all search…”
@jaypeedevlin · 2019-10-03 · source

Failure Signature (Search String)

  • Looks like www.python-requests.org and docs.python-requests.org are redirecting to https://2.python-requests.org and failing SSL negotiation, making the site appear down. Google
  • Redirection to https://2.python-requests.org breaks the site
Copy-friendly signature
signature.txt
Failure Signature ----------------- Looks like www.python-requests.org and docs.python-requests.org are redirecting to https://2.python-requests.org and failing SSL negotiation, making the site appear down. Google links are all dead, documentation links don't work, etc. Redirection to https://2.python-requests.org breaks the site

Error Message

Signature-only (no traceback captured)
error.txt
Error Message ------------- Looks like www.python-requests.org and docs.python-requests.org are redirecting to https://2.python-requests.org and failing SSL negotiation, making the site appear down. Google links are all dead, documentation links don't work, etc. Redirection to https://2.python-requests.org breaks the site

Minimal Reproduction

  1. Steps

What Broke

Users experienced broken links leading to documentation, causing confusion and inability to access resources.

Why It Broke

The documentation link in the README was pointing to an outdated URL that failed SSL negotiation

Fix Options (Details)

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

pip install requests==2.27.0

When NOT to use: This fix should not be used if the documentation is still hosted at the old URL.

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/5216

First fixed release: 2.27.0

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

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When NOT to Use This Fix

  • This fix should not be used if the documentation is still hosted at the old URL.

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?

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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

VersionStatus
2.27.0 Fixed

Related Issues

No related fixes found.

Sources

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