EMClient with RDP Windows 2016 DataCenter

I’m evaluating EMClient to replace Office 365 Outlook client on our Azure Cloud based  RDP server (Windows 2016 Datacenter) where we host about 30 users.

In testing EMClient, I can install it on a local Windows 10 desktop, enter my Office 365 email address and app password, and it works perfectly, finding and populating my account with my emails, contacts, calendar, etc.

However, if I try to do the same thing on a remote desktop session, it does not work. Nor does manually entering in the Office 365 SMTP, MAPI settings. I get error messages which say “authentication failed” is the response they are getting.

My point is the setup is exactly the same as what I do on a Windows 10 desktop which works perfectly, which is to say the default, automatic setup works fine on Windows 10 desktop.

However when I do the same thing on my remote desktop session no luck.

Note: Office 365 Outlook works and authenticates fine from the same remote desktop, using it’s automatic account search and setup. (no tweaking required) So I know it’s not a firewall issue, or connectivity issue, etc.

The reason I want to get rid of Outlook is to get rid of it’s security, which makes it a pain to use in conjunction with 3rd party apps, because you have to approve every email sent through it. My users cannot turn that off because they are not System Admins in an RDP environment. 

Just to add, the setup goes wrong almost immediately.

After I enter my email address on the desktop, it finds the account and asks me for my password. The next screen I see has my correct name and email address in the fields.

However when I do the same on the RDP desktop, it does NOT ask me for a password.  Instead it goes to the next screen and shows my email address under both the Name and Email Address fields.

So basically I can see that it is not detecting the account properly right from the start, yet it tries to go through and set it up anyway, and then just spits out errors.