I've got an active directory domain (2008 level) which predates our email moving to Exchange, so the domain names are different. The AD one is a ".local" created in the days before the best practice was to match external domain names. This means that email addresses (using our external domain) differ from internal identifiers. We now have an on-premise Exchange 2016 server. I've implemented autodiscover which was fine before Outlook 2016 came along as we could always specify the domain name in setting up. Now with Outlook 2016 the option to set this are so hard to discover that I decided to find out why I couldn't login to Outlook with just the external facing email address. It seems to work with setting up Outlook inside the domain, but I've got some external email users who don't have this option.
After much investigation, I found that the AD field userPrincipalName is set to email@example.com instead of firstname.lastname@example.org and that this governs whether you can login with the external email address on OWA. Here's the link that gave me the clue: https://social.technet.microsoft.com/Forums/en-US/15eef306-69b5-4008-904e-50e0116c223f/setup-outlook-anywhere-to-not-ask-for-domainusername-just-email-address-only?forum=exchange2010
So if I reset the field in the user's record in AD to the external email domain, I can then login with just the email address, and set up new Outlook 2016 profiles again with just the email address. So far this seems to work.
The question is whether this is good practice, or whether I should change my AD to use the external domain name, or some combination perhaps involving having both internal and external domains defined. Are there any gotchas if I simply change the userPrincipalName to match the email address in all cases?
I'm intending to migrate some of our mailboxes to Office 365 in the next month or two, so it would be good if there's a best practice to make this migration easier.