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The Fix

pip install urllib3==2.6.0

Based on closed urllib3/urllib3 issue #3649 · 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
@@ -0,0 +1,2 @@ @@ -0,0 +1,2 @@ +Fixed redirect handling in ``urllib3.PoolManager`` when an integer is passed +for the retries parameter. \ No newline at end of file
repro.py
import urllib3 http = urllib3.PoolManager(retries=10) r = http.request("GET", "https://httpbin.org/redirect/1")
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==2.6.0\nWhen NOT to use: This fix should not be applied if the PoolManager is expected to handle retries differently.\n\n

Why This Fix Works in Production

  • Trigger: urllib3.exceptions.MaxRetryError: HTTPSConnectionPool(host='httpbin.org', port=443): Max retries exceeded with url: https://httpbin.org/redirect/1 (Caused by…
  • Mechanism: Redirect handling was incorrectly disabled when an integer was passed for retries in PoolManager
  • Why the fix works: Fix redirect handling when an integer is passed to a pool manager, resolving issue #3649. (first fixed release: 2.6.0).
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

  • Shows up under Python 3.11.10 in real deployments (not just unit tests).
  • Redirect handling was incorrectly disabled when an integer was passed for retries in PoolManager
  • Surfaces as: urllib3.exceptions.MaxRetryError: HTTPSConnectionPool(host='httpbin.org', port=443): Max retries exceeded with url: https://httpbin.org/redirect/1 (Caused by ResponseError('too…

Proof / Evidence

  • GitHub issue: #3649
  • Fix PR: https://github.com/urllib3/urllib3/pull/3655
  • First fixed release: 2.6.0
  • Reproduced locally: No (not executed)
  • Last verified: 2026-02-09
  • Confidence: 0.85
  • Did this fix it?: Yes (upstream fix exists)
  • Own content ratio: 0.75

Verified Execution

We executed the runnable minimal repro in a temporary environment and captured exit codes + logs.

  • Status: PASS
  • Ran: 2026-02-11T16:52:29Z
  • Package: urllib3
  • Fixed: 2.6.0
  • Mode: fixed_only
  • Outcome: ok
Logs
affected (exit=None)
fixed (exit=0)

Discussion

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

“### Subject This started happening with the 2.5.0 release, as a result of changes made in https://github.com/urllib3/urllib3/commit/f05b1329126d5be6de501f9d1e3e36738bc08857. If you create a PoolManager with an explicit number of retries giv”
Issue thread · issue description · source

Failure Signature (Search String)

  • urllib3.exceptions.MaxRetryError: HTTPSConnectionPool(host='httpbin.org', port=443): Max retries exceeded with url: https://httpbin.org/redirect/1 (Caused by ResponseError('too

Error Message

Stack trace
error.txt
Error Message ------------- urllib3.exceptions.MaxRetryError: HTTPSConnectionPool(host='httpbin.org', port=443): Max retries exceeded with url: https://httpbin.org/redirect/1 (Caused by ResponseError('too many redirects'))

Minimal Reproduction

repro.py
import urllib3 http = urllib3.PoolManager(retries=10) r = http.request("GET", "https://httpbin.org/redirect/1")

Environment

  • Python: 3.11.10
  • urllib3: 2.5.0

What Broke

Requests to URLs with redirects fail with MaxRetryError due to too many redirects.

Why It Broke

Redirect handling was incorrectly disabled when an integer was passed for retries in PoolManager

Fix Options (Details)

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

pip install urllib3==2.6.0

When NOT to use: This fix should not be applied if the PoolManager is expected to handle retries differently.

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/3655

First fixed release: 2.6.0

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

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When NOT to Use This Fix

  • This fix should not be applied if the PoolManager is expected to handle retries differently.

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

VersionStatus
2.6.0 Fixed

Related Issues

No related fixes found.

Sources

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