This problem has been addressed countless times and yet I do not think there is a magic solution at least that worked for me. I perfectly was able to publish some private python packages to the Azure Artifacts so I can use them to build a bigger project but no, Azure decided that I won't be allowed to work on WSL or Docker. On windows I run pip install --index-url https://pkgs.dev.azure.com/MY_ORG... package-name it works absolutely perfectly. But as soon as I switch to WSL or Docker and follow the official and unofficial doc (updating pip, installing artifacts-keyring etc..) I stumble up the same wonderful error: ... ERROR: Could not install packages due to an OSError: HTTPSConnectionPool(host='....blob.core.windows.net', port=443): Max retries exceeded with url:... Very quickly adding the --trusted-host=...blob.core.windows.net works, sometimes, but obviously the URL changes every few seconds so it's not a forever fix. Continue reading...