Attempted to install AWS CLI on MSYS2 with pip and ran into the following issue:

pip3 search aws

WARNING: Retrying (Retry(total=4, connect=None, read=None, redirect=None, status=None)) after connection broken by 'SSLError(SSLCertVerificationError(1, '[SSL: CERTIFICATE_VERIFY_FAILED] certificate verify failed: self signed certificate in certificate chain (_ssl.c:1108)'))': /pypi

Although it was just a warning, the installation ultimately fails because of it. According to github.com/pypa/pip/issues/5288, whitelisting the package repositories fixes this issue. Sure enough, searching for aws with the trusted-host args works:

pip3 --trusted-host pypi.python.org --trusted-host files.pythonhosted.org --trusted-host pypi.org search aws

So I added the hosts to my pip configuration file:

mkdir -p ~/.config/pip/
touch ~/.config/pip/pip.conf
pip3 config --editor vim edit

touch ~/.config/pip/pip.conf

[global]
trusted-host=
  pypi.org
  pypi.python.org
  files.pythonhosted.org

Finally, installed AWS CLI:

pip3 install awscli

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