An redirect like from HTTP to HTTPS?
May I ask what SSL option have you got selected for your domain at SSL/TLS tab on Cloudflare dashboard (Flexible, Full, Strict …)?
Does it work when you temporarly make this DNS record cloud (unproxied)?
While visiting https://xxxxxx.com/Autodiscover/Autodiscover.xml, I got shown the homepage - without any redirect in the headers.
May I ask, shouldn’t it load the physical file from the server instead?
Also, is the file actually existing one at the origin host/server?
Furthermore, from my experience the autoconfig and autodiscover sub-domains which I use are both CNAME type pointed to my mail.domain.com (covered by an SSL certificate) and both of them (including A recordmail.domain.com) set on cloud.
mail.domain.com is pointed to my server IP (unproxied, cloud)
MX record for the domain.com is using mail.domain.com
Nevertheless, I use Let’s encrypt SSL certificate for mail.mydomain.com which works okay even with multiple domains on it (SNI), while for my naked domain.com and www.domain.com I use Cloudflare Origin CA certificate with the SSL option which is being set on Full (Strict) SSL.
Furthermore, may I ask what Outlook client version are you using?
If 2013, unfortunately, as far as I seen, even on older ones like Windows XP (not even supporting TLS v1.2 without Service Pack installed), you would have some issues due to the connection to your e-mail server as the SNI is being present in the SSL certificate (from Cloudflare) while having the cloud.
Please check the Exchange Certificate to make sure sub.xxxxxx.com, xxxxxx.com and www.xxxxxx.com is included.
it could be also if using cloud as it would end up with the different IP (Cloudflare one) as your Exchange server is it so it could not work either …
If so, better approach, using some sub-domain for this situation. Secure it with SSL. Try to connect over it - test while having it and (again, check your SSL/TLS tab).
I’m really sorry, I replaced our domain with the xxxx stuff. Can’t believe it converted to a porn site. So Even if I turn off the proxy it doesn’t work. Using testconnectivity.microsoft.com my activsync even fails now on the SSL… That piece was passing yesterday… ugh.