I've been using Office 365 Small Business (P1) since its launch back in 2011. It's a great service, and it's proven extremely reliable for my use. Coupled with my Lumia 920, it's a great user experience. Great mail, great collaborative doc editing, sharepoint, etc. For me to stick to a mail service for this long says a lot (especially if you look at my post history...oof).

My email address domain hasn't changed since 2006. I registered omfgoggles.net as a joke, set up my own mail server and have used that since I registered it. Last year, after having to repeat my address to people over and over, having to phoneticize it and spell it over the phone, I realized that it would be in my best interest to figure out something shorter. I shortened the username down to three characters, but it left the whole long 14 character domain+tld extension. Finally, I decided I'd buck up and just buy a shorter domain to give people that I would just alias to my regular address, providing me with a shorter option to read to people that wasn't on a totally different system (my other address is on outlook.com).

First course of action was to add the domain to Office 365, jump through the hoops (easy) to activate it, then add my desired address as an alias to my primary address. Totally straightforward. After some thought, I somehow convinced myself that maybe I should use the shorter address as my primary, so I changed my login and primary address to the new one. This is where things got screwy. After making the change, I left it for a few hours before realizing what a hideous, godawful pain in the ass it would be to have to change my address everywhere so I don't confuse myself, and how confusing or annoying it might be to my contacts to have another new address, etc. At this point, I changed it back.

I'm not sure what happened exactly, but somehow, my original address got put in some weird state of limbo within the Azure-based AD instance my domain lives in within Office365. At any rate, I messed with it, trying to remove the new domain, but had no luck. I'd remove the new address' alias, and would save the change, but when I went back to check, it was still there. I waited a couple hours after removing it one final time, realizing I wasn't making any progress, and submitted a post on Office365's community forum.

A couple hours later, a MS rep replied and suggested using Powershell with the Microsoft Online cmdlet to remove the domain. If you're interested in how that works, take a look here.

So, what did I do?

  • Connect Powershell's cmdlet to O365: connect-msolservice or, follow the guide in the previous link to write your creds locally so you don't have to type them out.

  • Next, execute:

    Set-MsolUserPrincipalName -UserPrincipalName [email protected] -NewUserPrincipalName [email protected]

Be sure you actually put legit addresses where [email protected] and [email protected] are. What this does is change your principal user within O365 from one user to another. The MS rep felt this would fix the ActiveSync issue I had as a result of stuff going sideways w/my domain. It relieved the issue and allowed me to remove the domain using...

  • This command: Remove-MsolDomain, which asks you which domain you'd like to remove? In my case, I only had a couple in the system so it was easy for me to type it in. You could also have it list all domains on your account by using Get-MsolDomain to show which domains they have provisioned in the system.

At this point, the new domain was blown out of AD and I was left with the old alias domain and my old primary domain. Cool. I then attempted to re-add my mail account to my phone, but it hung up on retrieving settings. I went into the Office365 admin panel to remove my phone's config from Exchange settings, but it was saying it couldn't find it provisioned as an endpoint at all. I figured this might be related to the domain's state within AD, and it turned out I was on the right track.

I used the tool here to test connectivity to O365 as my user, selecting first, the ActiveSync autodiscover test, then the ActiveSync w/inbox sync test tool. The output from the tool showed intermittent errors from the server depending on what content the tool tried retrieving. I found that if I used the generic "Exchange" profile config on my phone, under "Advanced", I could add my mail account to my phone but it wouldn't properly hook into any of the cool Sharepoint stuff. A side effect of setting it up this way was that I was finally able to delete it from the Exchange Admin panel on Office365. Now, this is where I got a little nervous about stuff.

This is what ended up fixing it for me:

  • I re-added the new domain.
  • Waited a few minutes, then set it as the primary domain (you can do this via the Admin panel, click your organization name in the top right corner, then changing it in the drop-down)
  • I added my alias for my new domain as my primary account.
  • Removed all old account aliases and accounts.
  • Removed the old domain from Office365.
  • Waited a few minutes for changes to propagate.
  • Re-added the domain to Office365, validated it, made NS changes.
  • Set the old domain back as the primary domain within the organization panel referenced earlier.
  • Changed the primary account back to my original email address.

At this point, my phone immediately finished setting itself up and everything functioned normally again.

I'm not entirely certain why it broke, because this seems like a pretty typical use case. I'm hoping that if anyone else encounters this, they might find my post on the community board or on the blog here and find it useful somehow. My own searches during troubleshooting didn't provide any insight into anything, since most of the issues I could find between Office365 and Windows Phone were related to bad practices by Verizon Wireless breaking IPv6 access on WP8 devices. That issue had its own failure mode with an actual error code and stuff. Unfortunately for me, my failure mode had no error code.