@Ben Woodman I'm glad that you were able to resolve your issue and thank you for posting your solution so that others experiencing the same thing can easily reference this! Since the Microsoft Q&A community has a policy that "The question author cannot accept their own answer. They can only accept answers by others ", I'll repost your solution in case you'd like to "Accept " the answer.
Issue: Azure Disk Encryption - Failing due to SSL/TLS secure connection
Error : A secure SSL/TLS connection could not be established,
Solution: The fix for this issue was to whitelist the processes below which were getting tunnelled via our proxy:
healthagent.exe windowsazureguestagent.exe bitlockeriaasvmextension.exe After whitelisting Azure Disk Encryption started working as expected.
Please let us know if you have any more questions and we will be glad to assist you further. Thank you!
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