Office 365 / Outlook Autodiscover and Certificate error behind roaming agent

We are currently using Umbrella with the virtual appliance in our offices. We are looking at switching to the Roaming agent to cover laptops when they're not in the office.

I can install the roaming agent and it works fine, the only issue I seem to have is with Office 365 Exchange mail and Outlook.

1) Autodiscover (setting up a new profile) does not work.

2) Existing profiles throw a certificate error and will not connect to Exchange behind the roaming agent

Per the article on the Roaming agent page, I added my existing "local domains" that were configured for the virtual appliances to the local domains list for the roaming agent as well.

I've also tried adding the Office 365 Outlook domains to the whitelist, but I don't seem show any results that they are getting blocked.

Can someone show an example of what should be in the Internal domains list and the whitelist for O365 Exchange to function with Outlook?

Office 365 / Outlook Autodiscover and Certificate error behind roaming agent

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