The Fix
pip install urllib3==1.25
Based on closed urllib3/urllib3 issue #764 · 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%.
@@ -199,9 +199,11 @@ have restrictions in their ``ssl`` module that limit the configuration that
features to be unavailable.
-If you encounter this warning, it is strongly recommended you upgrade to a
-newer Python version, or that you use pyOpenSSL as described in the
-:ref:`pyopenssl` section.
Option A — Upgrade to fixed release\npip install urllib3==1.25\nWhen NOT to use: This fix is not applicable if the underlying Python version cannot be upgraded.\n\n
Why This Fix Works in Production
- Trigger: The [documentation for InsecurePlatformWarning](https://urllib3.readthedocs.org/en/latest/security.html#insecureplatformwarning) suggests that to fix…
- Mechanism: The documentation did not include upgrading ndg-httpsclient as a solution for InsecurePlatformWarning
- Why the fix works: The documentation was updated to include upgrading ndg-httpsclient as a solution for InsecurePlatformWarning. (first fixed release: 1.25).
- 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 did not include upgrading ndg-httpsclient as a solution for InsecurePlatformWarning
- Production symptom (often without a traceback): The [documentation for InsecurePlatformWarning](https://urllib3.readthedocs.org/en/latest/security.html#insecureplatformwarning) suggests that to fix InsecurePlatformWarning messages you must either upgrade Python or use PyOpenSSL.
Proof / Evidence
- GitHub issue: #764
- Fix PR: https://github.com/urllib3/urllib3/pull/765
- 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: 0.67
Discussion
High-signal excerpts from the issue thread (symptoms, repros, edge-cases).
“ndg-httpsclient is mentioned here: https://urllib3.readthedocs.org/en/latest/security.html#openssl-pyopenssl But you're right, we should at least include the --upgrade flag in that example. Would you like to send a…”
Failure Signature (Search String)
- The [documentation for InsecurePlatformWarning](https://urllib3.readthedocs.org/en/latest/security.html#insecureplatformwarning) suggests that to fix InsecurePlatformWarning
- ndg-httpsclient is mentioned here: https://urllib3.readthedocs.org/en/latest/security.html#openssl-pyopenssl
Copy-friendly signature
Failure Signature
-----------------
The [documentation for InsecurePlatformWarning](https://urllib3.readthedocs.org/en/latest/security.html#insecureplatformwarning) suggests that to fix InsecurePlatformWarning messages you must either upgrade Python or use PyOpenSSL.
ndg-httpsclient is mentioned here: https://urllib3.readthedocs.org/en/latest/security.html#openssl-pyopenssl
Error Message
Signature-only (no traceback captured)
Error Message
-------------
The [documentation for InsecurePlatformWarning](https://urllib3.readthedocs.org/en/latest/security.html#insecureplatformwarning) suggests that to fix InsecurePlatformWarning messages you must either upgrade Python or use PyOpenSSL.
ndg-httpsclient is mentioned here: https://urllib3.readthedocs.org/en/latest/security.html#openssl-pyopenssl
Why It Broke
The documentation did not include upgrading ndg-httpsclient as a solution for InsecurePlatformWarning
Fix Options (Details)
Option A — Upgrade to fixed release Safe default (recommended)
pip install urllib3==1.25
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/765
First fixed release: 1.25
Last verified: 2026-02-09. Validate in your environment.
When NOT to Use This Fix
- This fix is not applicable if the underlying Python version cannot be upgraded.
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.
Sources
We don’t republish the full GitHub discussion text. Use the links above for context.