SSL handshake error with some Azure CLI commands

Question

I am using Azure CLI in bash within PowerShell in Windows 10. I sit behind a corporate proxy. My goal is to automate the deployment and setup of Azure resources.

Some of

Answer 1

I've updated this with my comment from https://github.com/Azure/azure-cli/issues/5099

@rzand 's process was the only one that worked for me, I'll expand on his solution though as there were extra steps required. All from elevated Shells

1. "C:\Program Files (x86)\Microsoft SDKs\Azure\CLI2\python" -m pip install --upgrade pip
2. "C:\Program Files (x86)\Microsoft Visual Studio\Shared\Python36_64\Scripts\pip" install python-certifi-win32
3. Add the Cloud services root CA to cacert.pem exported from the downloaded certificate. I specifically needed Microsoft IT TLS CA 5 and the "Baltimore CyberTrust Root" from that cert. Simply open the certs in text editor and append the contents to the bottom of C:\Program Files (x86)\Microsoft SDKs\Azure\CLI2\Lib\site-packages\certifi\cacert.pem
4. Add the Self-signed certificate given to you by the network team. Simply open the cert in text editor and append the contents to the bottom of C:\Program Files (x86)\Microsoft SDKs\Azure\CLI2\Lib\site-packages\certifi\cacert.pem
5. Set the system/environment variable in Command prompt setx /m REQUESTS_CA_BUNDLE "C:\Program Files (x86)\Microsoft SDKs\Azure\CLI2\Lib\site-packages\certifi\cacert.pem"
6. Set the system/environment variable in Powershell $env:REQUESTS_CA_BUNDLE="C:\Program Files (x86)\Microsoft SDKs\Azure\CLI2\Lib\site-packages\certifi\cacert.pem"
7. Close and open Bash / Command Prompt

FINALLY no errors. I can even retrieve Key Vault secrets