This is my first time using a cloudflare domain and dns setup but Autodiscover does not want to work correctly.
In the Outlook testing tool, I am getting failures for all of the Autodiscover calls.
I don’t see anything in there that points to Cloudflare.
The auto discover record is hosted in cloudflares dns
What’s the domain name?
Can you also post a screenshot of that DNS record here?
Without that info, all I can suggest is that you make sure that DNS record is set to 
DNS Only.