Inject SSL context into urllib3 ProxyManager, too #13343
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When a proxy is involved, requests uses a urllib3 proxy manager instead of the pool manager. We only inject our SSL context into the pool manager, which means the truststore context is lost when a proxy is set. We can modify proxy manager construction by overriding proxy_manager_for on the requests adapters.
uranusjr
approved these changes
Apr 22, 2025
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@ichard26 I currently have no access to the system I encountered it, but I will test it in roughly 2 weeks. Thanks a lot for investigating it! |
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We're not in a rush, no worries! |
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@ichard26 I finally got to testing your code change and it actually fixes the issue for me! So I did get a reproducing environment (working with pip < 24.2) and updated to the latest pip afterwards the issue was the same as described in #13288 . When installing the zip file via pip I was afterwards able to install packages without any other change to the env. Installing then again pip 25.1.1 and the issue appeared again. Thanks a lot for the investigation and the fix! |
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Thank you @schribl, glad to hear that this fixes the issue for you! |
This was referenced May 26, 2025
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When a proxy is involved, requests uses a urllib3 proxy manager instead of the pool manager. We only inject our SSL context into the pool manager, which means the truststore context is lost when a proxy is set.
We can modify proxy manager construction by overriding
proxy_manager_foron the requests adapters as described here: psf/requests#6109 (comment)I have no idea how to write a test for this (at least for the time being), so @schribl I'd appreciate if you could check whether this fixes your issue or not. You can install this branch via
pip install https://github.com/ichard26/pip/archive/bug/lost-ssl-context.zip. No rush!Should fix #13288.