TWC/RR email setup with Outlook/O365 - Time Warner Internet

This question is about "TWC/RR email setup with Outlook/O365", with Time Warner Cable internet and apps. I spent time on the phone with Microsoft and TWC/Spectrum yesterday trying to get my RR email account setup with Outlook. Of course as you can imagine, each is pointing to the other as the issue, which is frustrating to say the least.

The message in Outlook is that there is an SMTP SSL check failure. It's stating there is an invalid or expired certificate. I tried logging via an insecure connection, but it doesn't work either. And frankly, that's not what I would prefer to do.

I have it setup as IMAP using for incoming/outgoing servers. I've tried adding or leaving off the port extension, but no luck. Weird thing is that i'm able to setup using gmail. So i'm still not sure if it's a Microsoft or TWC/Spectrum issue.

Has anyone had any success or any thoughts on how to resolve?

TWC/RR email setup with Outlook/O365?