I ran into issues updating Expedition through my PAN Firewall running SSL decryption.
After a bit of troubleshooting there are two changes I needed to make on the expedition VM.
[global] cert = /etc/ssl/certs/ca-certificates.crt
I also needed to allow this system to download EXE's from the Internet, once PIP started trusting my decryption certificate, I discovered that PIP is downloading EXE's(normally for windows) as part of its script for some reason and this was causing it to throw errors.
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