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Requests https GET request fails with "handshake failure" (Fix)

Fixed
Spec
Package
Requests
Python
2.7
Dependency
urllib3 v1.8
Verdict
Status
Fixed
Safe for prod
No
Risk
Medium
Last verified
2026-02-04
Own content ratio
0.23
#2022 ai connection-leak corruption security tls Updated: 2026-02-13
Issue #2022

The Fix

I want to see if the workaround actually resolves the issue for confirmed cases ( this will mean I didnt screw something up while trying to do it).

Based on closed psf/requests issue #2022

Jump to Verify
repro.py
>> import requests >> requests.get('https://docs.apitools.com/2014/04/24/a-small-router-for-openresty.html') Traceback (most recent call last): File "<stdin>", line 1, in <module> File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/api.py", line 55, in get return request('get', url, **kwargs) File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/api.py", line 44, in request return session.request(method=method, url=url, **kwargs) File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/sessions.py", line 383, in request resp = self.send(prep, **send_kwargs) File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/sessions.py", line 486, in send r = adapter.send(request, **kwargs) File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/adapters.py", line 385, in send raise SSLError(e) requests.exceptions.SSLError: [Errno 1] _ssl.c:504: error:14077410:SSL routines:SSL23_GET_SERVER_HELLO:sslv3 alert handshake failure
verify
Re-run the minimal reproduction on your broken version, then apply the fix and re-run.
fix.md
Option A — Apply the official fix\nI want to see if the workaround actually resolves the issue for confirmed cases ( this will mean I didnt screw something up while trying to do it).\nWhen NOT to use: Do not use if it changes public behavior or if the failure cannot be reproduced.\n\nOption C — Workaround\nfor broken servers.`\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: >> import requests
  • Mechanism: I want to see if the workaround actually resolves the issue for confirmed cases ( this will mean I didnt screw something up while trying to do it).

Why This Breaks in Prod

  • Dependency interaction matters here: urllib3 v1.8.
  • Shows up under Python 2.7 in real deployments (not just unit tests).
  • Surfaces as: >> import requests

Proof / Evidence

  • GitHub issue: #2022
  • Reproduced locally: No (not executed)
  • Last verified: 2026-02-04
  • Confidence: 0.00
  • Did this fix it?: No (no upstream fix linked)
  • Own content ratio: 0.23

Discussion

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

Jump to Sources Open on GitHub
“Sadly, this is unrelated to the issue you identified, and entirely down to the crappy OpenSSL that OS X ships with by default”
@Lukasa · 2014-04-26 · source
“@jvanasco i'm still here. I was wondering, do you have a public URL i could test this with? I want to see if the workaround…”
@Lekinho · 2016-06-07 · confirmation · source
“No need to apologise, asking that question was the right thing to do: it's bizarrely specific knowledge to know that OS X has this problem.…”
@Lukasa · 2014-04-26 · source
“OK, I may have just answered my own question. What I did boils down to:”
@lsemel · 2015-09-25 · source

Failure Signature (Search String)

  • >> import requests

Error Message

Stack trace
error.txt
Error Message ------------- >> import requests >> requests.get('https://docs.apitools.com/2014/04/24/a-small-router-for-openresty.html') Traceback (most recent call last): File "<stdin>", line 1, in <module> File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/api.py", line 55, in get return request('get', url, **kwargs) File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/api.py", line 44, in request return session.request(method=method, url=url, **kwargs) File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/sessions.py", line 383, in request resp = self.send(prep, **send_kwargs) File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/sessions.py", line 486, in send r = adapter.send(request, **kwargs) File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/adapters.py", line 385, in send raise SSLError(e) requests.exceptions.SSLError: [Errno 1] _ssl.c:504: error:14077410:SSL routines:SSL23_GET_SERVER_HELLO:sslv3 alert handshake failure
Stack trace
error.txt
Error Message ------------- >> adapter = SSLAdapter('TLSv1') >> s = requests.Session() >> s.mount('https://', adapter) >> s.get('https://docs.apitools.com/2014/04/24/a-small-router-for-openresty.html') Traceback (most recent call last): File "<stdin>", line 1, in <module> File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/sessions.py", line 395, in get return self.request('GET', url, **kwargs) File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/sessions.py", line 383, in request resp = self.send(prep, **send_kwargs) File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/sessions.py", line 486, in send r = adapter.send(request, **kwargs) File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/adapters.py", line 385, in send raise SSLError(e) requests.exceptions.SSLError: [Errno 1] _ssl.c:504: error:14094410:SSL routines:SSL3_READ_BYTES:sslv3 alert handshake failure
Stack trace
error.txt
Error Message ------------- >> adapter = SSLAdapter('SSLv3') >> s = requests.Session() >> s.mount('https://', adapter) >> s.get('https://docs.apitools.com/2014/04/24/a-small-router-for-openresty.html') Traceback (most recent call last): File "<stdin>", line 1, in <module> File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/sessions.py", line 395, in get return self.request('GET', url, **kwargs) File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/sessions.py", line 383, in request resp = self.send(prep, **send_kwargs) File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/sessions.py", line 486, in send r = adapter.send(request, **kwargs) File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/adapters.py", line 385, in send raise SSLError(e) requests.exceptions.SSLError: [Errno 1] _ssl.c:504: error:14094410:SSL routines:SSL3_READ_BYTES:sslv3 alert handshake failure

Minimal Reproduction

repro.py
>> import requests >> requests.get('https://docs.apitools.com/2014/04/24/a-small-router-for-openresty.html') Traceback (most recent call last): File "<stdin>", line 1, in <module> File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/api.py", line 55, in get return request('get', url, **kwargs) File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/api.py", line 44, in request return session.request(method=method, url=url, **kwargs) File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/sessions.py", line 383, in request resp = self.send(prep, **send_kwargs) File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/sessions.py", line 486, in send r = adapter.send(request, **kwargs) File "/Users/jaddison/.virtualenvs/techtown/lib/python2.7/site-packages/requests/adapters.py", line 385, in send raise SSLError(e) requests.exceptions.SSLError: [Errno 1] _ssl.c:504: error:14077410:SSL routines:SSL23_GET_SERVER_HELLO:sslv3 alert handshake failure

Environment

  • Python: 2.7
  • urllib3: 1.8

Fix Options (Details)

Option A — Apply the official fix

I want to see if the workaround actually resolves the issue for confirmed cases ( this will mean I didnt screw something up while trying to do it).

When NOT to use: Do not use if it changes public behavior or if the failure cannot be reproduced.

Option C — Workaround Temporary workaround

for broken servers.`

When NOT to use: Do not use if it changes public behavior or if the failure cannot be reproduced.

Use only if you cannot change versions today. Treat this as a stopgap and remove once upgraded.

Fix reference: https://github.com/psf/requests/issues/2022

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When NOT to Use This Fix

  • Do not use if it changes public behavior or if the failure cannot be reproduced.

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 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.
  • Track RSS + object counts after deployments; alert on monotonic growth and GC pressure.
  • Add a long-running test that repeats the failing call path and asserts stable memory.

Related Issues

No related fixes found.

Cluster: requests:ssl-handshake Requests hub Requests best practices All hubs All clusters
Related clusters: Configuration error Data consistency Other

Sources

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

Source & Disclaimer: Analysis derived from GitHub Issue #2022. Not affiliated with the library maintainers. Verify before production use.