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Add troubleshooting guidance for SSL verification errors#7556

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LKoech wants to merge 2 commits into
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LKoech:docs/ssl-troubleshooting
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Add troubleshooting guidance for SSL verification errors#7556
LKoech wants to merge 2 commits into
psf:mainfrom
LKoech:docs/ssl-troubleshooting

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@LKoech

@LKoech LKoech commented Jul 3, 2026

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Closes #7547

Adds a "Troubleshooting SSL Errors" subsection to the SSL Cert
Verification section in docs/user/advanced.rst, covering:

  • common causes of SSL verification failures
  • how to diagnose which check failed (error message, openssl, clock)
  • how to fix each cause
  • when verify=False is acceptable and its security implications

Docs-only change. Line width kept under 79 chars and Python examples
use single quotes per the contributor guide.

vamsiduppala added a commit to vamsiduppala/thereviewman2 that referenced this pull request Jul 4, 2026
…ion suite

- pallets/click#3642 (merged, code+test), psf/requests#7556 (open, docs-only,
  one 152-line hunk), Kludex/starlette#3360 (open, 3-file code+test)
- REST payloads captured verbatim (provenance in each meta.json); diffs
  computed from the PRs' real git objects via the git transport
- e2e proves parser/chunker reproduce GitHub's own accounting exactly:
  per-file +/- counts, file counts, PR totals, on all three PRs
- real-data split-hunk test (requests mega-hunk at budget 400)
- 42 offline tests + 2 live-marked; ruff + mypy --strict clean
Comment thread docs/user/advanced.rst
Comment on lines +254 to +268
Security Implications of Disabling SSL Verification (``verify=False``)
^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^^

- Man-in-the-middle (MitM) attacks are a form of active eavesdropping
in which the attacker intercepts or impersonates the server, especially
on public networks.

- Data exposure, where all data transmitted over the network can be
intercepted and read by the attacker. This includes sensitive information
such as login credentials, personal data and financial information.

- Regulatory and compliance issues with regulations like SOC 2 and
GDPR regarding data security and privacy. Disabling SSL verification
can lead to non-compliance with these regulations, resulting in legal
consequences and reputational damage.

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This is unnecessary. You're repeating what's already said above.

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yeah that's true, thanks for pointing that out.

Comment thread docs/user/advanced.rst
``verify='/path/to/certfile'`` is better because it allows you to
validate the server's certificate against a known trusted certificate,
providing a higher level of security than disabling verification entirely.

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Again, you've just generated way more words than what was already said above adding no value

Comment thread docs/user/advanced.rst
validate the server's certificate against a known trusted certificate,
providing a higher level of security than disabling verification entirely.

Troubleshooting SSL Verification Errors

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This is the only section actually requested.

Comment thread docs/user/advanced.rst
Comment on lines +295 to +297
- Outdated or missing CA certificates on the client machine.
Requests trust the CAs shipped by the ``certifi`` package, which
may be old or may not include the CA that signed the server's certificate.

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"Outdated" is unlikely. CAs are not added that frequently to the bundle. When CAs expire, they can stay in the bundle. It's not likely that. It's most likely someone using an expired certificate, a self-signed certificate, or a CA that's not a public CA (e.g., internal PKI implementations).

You've added lots and lots of text here that's not addressing the most common problems.

Comment thread docs/user/advanced.rst

- Old Python version or OpenSSL library that does not support modern TLS protocols.

- An expired certificate on the server. The server's certificate may have expired,

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There's no example of what this would look like as an error and it's easily the most common one.

Comment thread docs/user/advanced.rst
Comment on lines +324 to +327



Diagnosing the problem can be done by following these steps:

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Why so many new lines?

Oh this is "AI" drivel. Might as well stop reviewing now. You put zero real effort into reviewing this at all eh?

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Documentation suggestion: Add troubleshooting guidance for common SSL verification errors

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