@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. Accepted answers show up at the top, resulting in improved discoverability for others.
Issue: When trying to enable ADE on our Azure Virtual Machines they keep failing due to an error: System.Net.WebException: The request was aborted: Could not create SSL/TLS secure channel.
Cause: Customer proxy was causing this issue.
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