urllib3 pypy tests often fail in CI with reason "cancelled

The Fix

pip install urllib3==2.2.0

Based on closed urllib3/urllib3 issue #3305 · 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

@@ -67,7 +67,7 @@ jobs:
             experimental: false
             nox-session: test-pypy
-          - python-version: "pypy-3.9"
+          - python-version: "pypy-3.9-v7.3.13"
             os: ubuntu-latest

repro.py

nox -s ${NOX_SESSION:-test-$PYTHON_VERSION}
  shell: /usr/bin/bash --noprofile --norc -e -o pipefail {0}
  env:
    pythonLocation: /opt/hostedtoolcache/PyPy/3.9.18/x64
    Python_ROOT_DIR: /opt/hostedtoolcache/PyPy/3.9.18/x64
    Python2_ROOT_DIR: /opt/hostedtoolcache/PyPy/3.9.18/x64
    Python3_ROOT_DIR: /opt/hostedtoolcache/PyPy/3.9.18/x64
    PKG_CONFIG_PATH: /opt/hostedtoolcache/PyPy/3.9.18/x64/bin/lib/pkgconfig
    PYTHON_VERSION: pypy-3.9
    NOX_SESSION: test-pypy3.9
nox > Running session test-pypy3.9
nox > Creating virtual environment (virtualenv) using pypy3.9 in .nox/test-pypy3-9
nox > python -m pip install -r dev-requirements.txt
nox > python -m pip install '.[socks,brotli,zstd,h2]'
nox > pip --version
pip 23.3.1 from /home/runner/work/urllib3/urllib3/.nox/test-pypy3-9/lib/pypy3.9/site-packages/pip (python 3.9)
nox > python --version
Python 3.9.18 (9c4f8ef178b6, Jan 14 2024, 11:28:13)
[PyPy 7.3.15 with GCC 10.2.1 20210130 (Red Hat 10.2.1-11)]
nox > python -c 'import struct; print(struct.calcsize('"'"'P'"'"') * 8)'
64
nox > python -m OpenSSL.debug
pyOpenSSL: 23.2.0
cryptography: 41.0.6
cffi: 1.16.0
cryptography's compiled against OpenSSL: OpenSSL 3.1.4 24 Oct 2023
cryptography's linked OpenSSL: OpenSSL 3.1.4 24 Oct 2023
Python's OpenSSL: OpenSSL 3.0.12 24 Oct 2023
Python executable: /home/runner/work/urllib3/urllib3/.nox/test-pypy3-9/bin/python
Python version: 3.9.18 (9c4f8ef178b6, Jan 14 2024, 11:28:13)
[PyPy 7.3.15 with GCC 10.2.1 20210130 (Red Hat 10.2.1-11)]
Platform: linux
sys.path: ['/home/runner/work/urllib3/urllib3', '/opt/hostedtoolcache/PyPy/3.9.18/x64/lib/pypy3.9', '/home/runner/work/urllib3/urllib3/.nox/test-pypy3-9/lib/pypy3.9/site-packages']
nox > python -c 'import sys; print(sys.implementation.name, sys.version_info.releaselevel)'
nox > python -m coverage run --parallel-mode -m pytest -v -ra --color=yes --tb=native --durations=10 --strict-config --strict-markers test/
============================= test session starts ==============================
platform linux -- Python 3.9.18[pypy-7.3.15-final], pytest-7.4.2, pluggy-1.3.0 -- /home/runner/work/urllib3/urllib3/.nox/test-pypy3-9/bin/python
cachedir: .pytest_cache
rootdir: /home/runner/work/urllib3/urllib3
configfile: pyproject.toml
plugins: anyio-4.2.0, timeout-2.1.0
collecting ... collected 2085 items / 1 skipped

test/test_collections.py::TestLRUContainer::test_maxsize PASSED          [  0%]
...
test/contrib/test_pyopenssl.py::TestSSL::test_is_ipaddress_false[v2.sg.media-imdb.com1] PASSED [ 51%]
Error: The operation was canceled.

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==2.2.0\nWhen NOT to use: This fix is not suitable if a different PyPy version is required for compatibility.\n\n

Why This Fix Works in Production

Trigger: Error: The operation was canceled.
Mechanism: The CI was timing out due to the PyPy version causing excessive test durations
Why the fix works: Pins the PyPy version in CI to prevent timeouts during tests. (first fixed release: 2.2.0).

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 3.9 in real deployments (not just unit tests).
The CI was timing out due to the PyPy version causing excessive test durations
Surfaces as: Error: The operation was canceled.

Proof / Evidence

GitHub issue: #3305
Fix PR: https://github.com/urllib3/urllib3/pull/3308
First fixed release: 2.2.0
Reproduced locally: No (not executed)
Last verified: 2026-02-09
Confidence: 0.95
Did this fix it?: Yes (upstream fix exists)
Own content ratio: 0.48

Discussion

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

Jump to Sources Open on GitHub

“### Subject I have submitted a couple of PRs and it feel like I never got a passing CI , usually it fails on pypy3.9 with "cancelled after 30m". Looking at the logs of the CI jobs the test suite is around 50% when the CI job is killed. ###”

Issue thread · issue description · source

Failure Signature (Search String)

Error: The operation was canceled.

Error Message

Stack trace

error.txt

Error Message
-------------
Error: The operation was canceled.

Minimal Reproduction

repro.py

nox -s ${NOX_SESSION:-test-$PYTHON_VERSION}
  shell: /usr/bin/bash --noprofile --norc -e -o pipefail {0}
  env:
    pythonLocation: /opt/hostedtoolcache/PyPy/3.9.18/x64
    Python_ROOT_DIR: /opt/hostedtoolcache/PyPy/3.9.18/x64
    Python2_ROOT_DIR: /opt/hostedtoolcache/PyPy/3.9.18/x64
    Python3_ROOT_DIR: /opt/hostedtoolcache/PyPy/3.9.18/x64
    PKG_CONFIG_PATH: /opt/hostedtoolcache/PyPy/3.9.18/x64/bin/lib/pkgconfig
    PYTHON_VERSION: pypy-3.9
    NOX_SESSION: test-pypy3.9
nox > Running session test-pypy3.9
nox > Creating virtual environment (virtualenv) using pypy3.9 in .nox/test-pypy3-9
nox > python -m pip install -r dev-requirements.txt
nox > python -m pip install '.[socks,brotli,zstd,h2]'
nox > pip --version
pip 23.3.1 from /home/runner/work/urllib3/urllib3/.nox/test-pypy3-9/lib/pypy3.9/site-packages/pip (python 3.9)
nox > python --version
Python 3.9.18 (9c4f8ef178b6, Jan 14 2024, 11:28:13)
[PyPy 7.3.15 with GCC 10.2.1 20210130 (Red Hat 10.2.1-11)]
nox > python -c 'import struct; print(struct.calcsize('"'"'P'"'"') * 8)'
64
nox > python -m OpenSSL.debug
pyOpenSSL: 23.2.0
cryptography: 41.0.6
cffi: 1.16.0
cryptography's compiled against OpenSSL: OpenSSL 3.1.4 24 Oct 2023
cryptography's linked OpenSSL: OpenSSL 3.1.4 24 Oct 2023
Python's OpenSSL: OpenSSL 3.0.12 24 Oct 2023
Python executable: /home/runner/work/urllib3/urllib3/.nox/test-pypy3-9/bin/python
Python version: 3.9.18 (9c4f8ef178b6, Jan 14 2024, 11:28:13)
[PyPy 7.3.15 with GCC 10.2.1 20210130 (Red Hat 10.2.1-11)]
Platform: linux
sys.path: ['/home/runner/work/urllib3/urllib3', '/opt/hostedtoolcache/PyPy/3.9.18/x64/lib/pypy3.9', '/home/runner/work/urllib3/urllib3/.nox/test-pypy3-9/lib/pypy3.9/site-packages']
nox > python -c 'import sys; print(sys.implementation.name, sys.version_info.releaselevel)'
nox > python -m coverage run --parallel-mode -m pytest -v -ra --color=yes --tb=native --durations=10 --strict-config --strict-markers test/
============================= test session starts ==============================
platform linux -- Python 3.9.18[pypy-7.3.15-final], pytest-7.4.2, pluggy-1.3.0 -- /home/runner/work/urllib3/urllib3/.nox/test-pypy3-9/bin/python
cachedir: .pytest_cache
rootdir: /home/runner/work/urllib3/urllib3
configfile: pyproject.toml
plugins: anyio-4.2.0, timeout-2.1.0
collecting ... collected 2085 items / 1 skipped

test/test_collections.py::TestLRUContainer::test_maxsize PASSED          [  0%]
...
test/contrib/test_pyopenssl.py::TestSSL::test_is_ipaddress_false[v2.sg.media-imdb.com1] PASSED [ 51%]
Error: The operation was canceled.

Environment

Python: 3.9

What Broke

CI jobs were cancelled after exceeding the 30-minute timeout limit.

Why It Broke

The CI was timing out due to the PyPy version causing excessive test durations

Fix Options (Details)

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

pip install urllib3==2.2.0

When NOT to use: This fix is not suitable if a different PyPy version is required for compatibility.

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

Option D — Guard side-effects with OnceOnly Guardrail for side-effects

Mitigate duplicate external side-effects under retries/timeouts/agent loops by gating the operation before calling external systems.

Place OnceOnly between your code/agent and real side-effects (Stripe, emails, CRM, APIs).
Use a stable key per side-effect (e.g., customer_id + action + idempotency_key).
Fail-safe: configure fail-open vs fail-closed based on blast radius and spend risk.

Show example snippet (optional)

onceonly.py

from onceonly import OnceOnly
import os

once = OnceOnly(api_key=os.environ["ONCEONLY_API_KEY"], fail_open=True)

# Stable idempotency key per real side-effect.
# Use a request id / job id / webhook delivery id / Stripe event id, etc.
event_id = "evt_..."  # replace
key = f"stripe:webhook:{event_id}"

res = once.check_lock(key=key, ttl=3600)
if res.duplicate:
    return {"status": "already_processed"}

# Safe to execute the side-effect exactly once.
handle_event(event_id)

See OnceOnly SDK

When NOT to use: Do not use this to hide logic bugs or data corruption. Use it to block duplicate external side-effects and enforce tool permissions/spend caps.

Fix reference: https://github.com/urllib3/urllib3/pull/3308

First fixed release: 2.2.0

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

When NOT to Use This Fix

This fix is not suitable if a different PyPy version is required for compatibility.
Do not use this to hide logic bugs or data corruption. Use it to block duplicate external side-effects and enforce tool permissions/spend caps.

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

Version	Status
2.2.0	Fixed

Related Issues

No related fixes found.

Cluster: urllib3:configuration-error urllib3 hub urllib3 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.

urllib3 pypy tests often fail in CI with reason "cancelled after 30 minutes" (Fix)