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The Fix

pip install requests==2.27.0

Based on closed psf/requests issue #5212 · 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
@@ -3,8 +3,8 @@ following: -1. Read our [Contributor's Guide](http://docs.python-requests.org/en/latest/dev/contributing/). -2. Understand our [development philosophy](http://docs.python-requests.org/en/latest/dev/philosophy/). +1. Read our [Contributor's Guide](https://requests.readthedocs.io/en/latest/dev/contributing/).
repro.py
>> import requests >> requests.get('https://2.python-requests.org/') Traceback (most recent call last): File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/urllib3/contrib/pyopenssl.py", line 472, in wrap_socket cnx.do_handshake() File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/OpenSSL/SSL.py", line 1716, in do_handshake self._raise_ssl_error(self._ssl, result) File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/OpenSSL/SSL.py", line 1456, in _raise_ssl_error _raise_current_error() File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/OpenSSL/_util.py", line 54, in exception_from_error_queue raise exception_type(errors) OpenSSL.SSL.Error: [('SSL routines', 'ssl3_read_bytes', 'tlsv1 alert internal error')] During handling of the above exception, another exception occurred: Traceback (most recent call last): File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/urllib3/connectionpool.py", line 603, in urlopen chunked=chunked) File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/urllib3/connectionpool.py", line 344, in _make_request self._validate_conn(conn) File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/urllib3/connectionpool.py", line 843, in _validate_conn conn.connect() File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/urllib3/connection.py", line 370, in connect ssl_context=context) File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/urllib3/util/ssl_.py", line 355, in ssl_wrap_socket return context.wrap_socket(sock, server_hostname=server_hostname) File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/urllib3/contrib/pyopenssl.py", line 478, in wrap_socket raise ssl.SSLError('bad handshake: %r' % e) ssl.SSLError: ("bad handshake: Error([('SSL routines', 'ssl3_read_bytes', 'tlsv1 alert internal error')],)",) During handling of the above exception, another exception occurred: Traceback (most recent call last): File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/requests/adapters.py", line 449, in send timeout=timeout File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/urllib3/connectionpool.py", line 641, in urlopen _stacktrace=sys.exc_info()[2]) File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/urllib3/util/retry.py", line 399, in increment raise MaxRetryError(_pool, url, error or ResponseError(cause)) urllib3.exceptions.MaxRetryError: HTTPSConnectionPool(host='2.python-requests.org', port=443): Max retries exceeded with url: / (Caused by SSLError(SSLError("bad handshake: Error([('SSL routines', 'ssl3_read_bytes', 'tlsv1 alert internal error')],)",),)) During handling of the above exception, another exception occurred: Traceback (most recent call last): File "<stdin>", line 1, in <module> File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/requests/api.py", line 75, in get return request('get', url, params=params, **kwargs) File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/requests/api.py", line 60, in request return session.request(method=method, url=url, **kwargs) File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/requests/sessions.py", ... (truncated) ...
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 requests==2.27.0\nWhen NOT to use: This fix is not applicable if the documentation needs to reference the old site for legacy support.\n\n

Why This Fix Works in Production

  • Trigger: >> import requests
  • Mechanism: The documentation contained outdated links that pointed to a non-existent HTTPS version of the site
  • Why the fix works: Updated documentation links to point to requests.readthedocs.io instead of the deprecated 2.python-requests.org. (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

  • Shows up under Python 3.6 in real deployments (not just unit tests).
  • The documentation contained outdated links that pointed to a non-existent HTTPS version of the site
  • Surfaces as: >> import requests

Proof / Evidence

  • GitHub issue: #5212
  • Fix PR: https://github.com/psf/requests/pull/5236
  • First fixed release: 2.27.0
  • Reproduced locally: No (not executed)
  • Last verified: 2026-02-07
  • Confidence: 0.75
  • Did this fix it?: Yes (upstream fix exists)
  • Own content ratio: 0.30

Discussion

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

“Can you fix up the redirect from docs.pyhon-requests.org' so that it doesn't redirect to a URL that cannot work? http://docs.python-requests.org/en/master/objects.inv -> https://2.python-requests.org//en/master/objects.inv which now doesn't…”
@ashb · 2019-09-25 · source
“URL in readme was changed by @Leetcore https://github.com/psf/requests/commit/74b72ce4265583db0430080ab67d3d5e0c4b44b2 Closing this issue, as 2.python-requests.org is no longer mentioned anywhere in docs”
@chmreid · 2019-10-17 · confirmation · source
“Re-opening until @ssbarnea's pull request #5236 is merged, since there are a lot more links than I initially thought when I closed this issue”
@chmreid · 2019-10-19 · confirmation · source
“I moved the site to requests.kennethreitz.org, in preparation to it being requests.psf.org (or something similar, ideally).”
@kennethreitz · 2019-09-25 · source

Failure Signature (Search String)

  • >> import requests

Error Message

Stack trace
error.txt
Error Message ------------- >> import requests >> requests.get('https://2.python-requests.org/') Traceback (most recent call last): File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/urllib3/contrib/pyopenssl.py", line 472, in wrap_socket cnx.do_handshake() File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/OpenSSL/SSL.py", line 1716, in do_handshake self._raise_ssl_error(self._ssl, result) File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/OpenSSL/SSL.py", line 1456, in _raise_ssl_error _raise_current_error() File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/OpenSSL/_util.py", line 54, in exception_from_error_queue raise exception_type(errors) OpenSSL.SSL.Error: [('SSL routines', 'ssl3_read_bytes', 'tlsv1 alert internal error')] During handling of the above exception, another exception occurred: Traceback (most recent call last): File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/urllib3/connectionpool.py", line 603, in urlopen chunked=chunked) File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/urllib3/connectionpool.py", line 344, in _make_request self._validate_conn(conn) File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/urllib3/connectionp ... (truncated) ...

Minimal Reproduction

repro.py
>> import requests >> requests.get('https://2.python-requests.org/') Traceback (most recent call last): File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/urllib3/contrib/pyopenssl.py", line 472, in wrap_socket cnx.do_handshake() File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/OpenSSL/SSL.py", line 1716, in do_handshake self._raise_ssl_error(self._ssl, result) File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/OpenSSL/SSL.py", line 1456, in _raise_ssl_error _raise_current_error() File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/OpenSSL/_util.py", line 54, in exception_from_error_queue raise exception_type(errors) OpenSSL.SSL.Error: [('SSL routines', 'ssl3_read_bytes', 'tlsv1 alert internal error')] During handling of the above exception, another exception occurred: Traceback (most recent call last): File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/urllib3/connectionpool.py", line 603, in urlopen chunked=chunked) File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/urllib3/connectionpool.py", line 344, in _make_request self._validate_conn(conn) File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/urllib3/connectionpool.py", line 843, in _validate_conn conn.connect() File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/urllib3/connection.py", line 370, in connect ssl_context=context) File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/urllib3/util/ssl_.py", line 355, in ssl_wrap_socket return context.wrap_socket(sock, server_hostname=server_hostname) File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/urllib3/contrib/pyopenssl.py", line 478, in wrap_socket raise ssl.SSLError('bad handshake: %r' % e) ssl.SSLError: ("bad handshake: Error([('SSL routines', 'ssl3_read_bytes', 'tlsv1 alert internal error')],)",) During handling of the above exception, another exception occurred: Traceback (most recent call last): File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/requests/adapters.py", line 449, in send timeout=timeout File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/urllib3/connectionpool.py", line 641, in urlopen _stacktrace=sys.exc_info()[2]) File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/urllib3/util/retry.py", line 399, in increment raise MaxRetryError(_pool, url, error or ResponseError(cause)) urllib3.exceptions.MaxRetryError: HTTPSConnectionPool(host='2.python-requests.org', port=443): Max retries exceeded with url: / (Caused by SSLError(SSLError("bad handshake: Error([('SSL routines', 'ssl3_read_bytes', 'tlsv1 alert internal error')],)",),)) During handling of the above exception, another exception occurred: Traceback (most recent call last): File "<stdin>", line 1, in <module> File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/requests/api.py", line 75, in get return request('get', url, params=params, **kwargs) File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/requests/api.py", line 60, in request return session.request(method=method, url=url, **kwargs) File "/Users/charles/.pyenv/versions/miniconda3-4.3.30/lib/python3.6/site-packages/requests/sessions.py", ... (truncated) ...

Environment

  • Python: 3.6

What Broke

Users encountered broken links leading to a non-functional HTTPS site, causing confusion.

Why It Broke

The documentation contained outdated links that pointed to a non-existent HTTPS version of the site

Fix Options (Details)

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

pip install requests==2.27.0

When NOT to use: This fix is not applicable if the documentation needs to reference the old site for legacy support.

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/5236

First fixed release: 2.27.0

Last verified: 2026-02-07. Validate in your environment.

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When NOT to Use This Fix

  • This fix is not applicable if the documentation needs to reference the old site for legacy support.

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.

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.