How can I troubleshoot pip installations behind a proxy using CNTLM?

Troubleshooting Proxy-Based pip Installations with CNTLM

When implementing pip behind a proxy using CNTLM, users may encounter difficulties ensuring its proper configuration. To verify its functionality, consider the following steps:

Run the command:

cntlm.exe -c cntlm.ini -I -M http://google.com

If this command fails with a "Connection to proxy failed" error, it indicates an issue with your CNTLM setup.

Furthermore, using the command:

pip install --proxy=user:pass@localhost:3128

where "user" and "pass" are your proxy credentials, may result in an error fetching the index base URL.

Alternative Solution

If CNTLM proves problematic, you can alternatively set the https_proxy environment variable to point to your proxy server. Note that this variable is different from http_proxy. Execute the command:

export https_proxy=http://web-proxy.mydomain.com

This will route all HTTPS requests, including those made by pip, through your proxy server.

Finally, run the following command to install a package using pip:

sudo -E pip install somepackage

This command ensures that the https_proxy environment variable is inherited during the installation process.

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