Comment by thewisenerd

slightly related, one of the more interesting issues i've faced due to mitm tls by the $job mandated CASB (cloud-access security broker)

is when python 3.13 [1] introduced some stricter validations and the CASB issued certs were not compliant (missing AKI); which broke REQUESTS_CA_BUNDLE/SSL_CERT_FILE for us

[1] https://discuss.python.org/t/python-3-13-x-ssl-security-chan...