Office 365 Transition Notes – transitioning my family was a snap, once I stopped trying to outgeek the process

Well, I had a pretty painful Office 365 transition for this past weekend. However, I can now honestly say that most of it was my fault.  And the reason is, I signed up for the P1 plan which has no human support (just community/forum posts) and that I was simply too impatient.

Basically, between trying to rush DNS and trying to coordinate people (connecting to 6 family members so I could migrate their mailboxes and their phones, was maddening).

Here’s what I learned, because otherwise the service is pretty slick.

  1. Be patient. When they say something could take up to 72 hours, they mean it. Even DNS.  I was furiously proving to them that my DNS settings had propagated to every DNS server I tested against but my domain wouldn’t verify.  This is because they have internal processes (and scripts and such) and their own internal systems take as much time as their process does.  Lesson: No client migration should start on a Friday night and be expected to be done on the Monday AM.  Instead, start the DNS, etc. process a week in advance, get your ducks in a row and then schedule the actual cutover
  2. You can migrate email in pieces but the deal is this… all mail needs to go through your old system and then get routed to the new system, if you are moving mailboxes one at a time (you can’t do Office 365, forwarded back to on premise) as there is no way to provision an upstream routing path – no big deal, but just know this is true

Why I Did It

Because I’m Bat Shit Crazy.  And…

While a family SharePoint site collection is in the cards and Lync could be fun, I did it because I’m tired of supporting POP3 for family members. Email on desktops get lost, crappy anti-spam/antivirus and now they can access ALL (25gb worth) of their email from their phones, webmail and Outlook 2007 or better.  Sweet. My time is worth that.

Settings You’ll Want To Know

  • – to administer your setup, this is the primary URL
  • – this is the DNS website Microsoft recommends you use for validating your DNS.  While there are hundreds out there, you might as well check against this one, as that is where their tech support is looking
  • The name servers to point your domain at Microsoft (after you have verified the domain, you can configure either a bogus MX record or a TXT record – be patient when configuring this!!) will be: and
  • If you are like me, you’ll want to have a custom Webmail alias that you can remember, such as If you do, you’ll want to create a CNAME record that points to


On to some random notes and screenshots

  • I went for P1 ($6/user a month for up to 50 users, 1 shared SharePoint Site Collection, OWA (Office Web Apps), Lync, etc. and of course, 25GB mailboxes per user with Webmail, ActiveSync and Outlook Anywhere


  • You can create your own records when/if you decide to have Microsoft host the DNS for the domain (you don’t have to, but considering all the records involved, you might just want to).



  • You can have several domains pointed to the same account as I did (, and – the latter two being the domains for my dad’s business)

SNAGHTML211da782 is the domain that you start with and as such, you can do lots of testing with.

  • If you find you can’t configure an Outlook account (autodiscover works a treat in Outlook and iPhones), it is probably because the users account wants a password reset.  Login to as the user to get prompted for the password change and then retry Outlook setup again.


SLA’s are transparent and reasonably honest



  • You can run Powershell against your setup. Yep, its true.  Check out my OneNote for the settings I needed to do to force FOPE (Microsoft’s Forefront Anti-Spam platform) to trust my domain for inbound email after a (too quick) DNS move

You Can Have Forwarders/Aliases that deliver email to other systems

But it’s a little tricky…

For example, my sister didn’t want to be on the platform but she has had a email for years.  So I wanted to send [email protected] (her name isn’t Joe BTW Winking smile) to [email protected]

The trick is four (and a 1/2) things:

1. Create an external contact


2. Create a Distribution List (yep, even for just one person)


3. Add the External Contact as a Recipient (This is the 1/2 as well by the way, in that you will want to remove your admin account as a member, or plan on getting everyone’s spam as you’ll be added by default)


4. You then need to allow the Distribution Group to accept emails from outside Office 365 (and this is why you need the Distribution Group, because you can’t set this on the External Contact). Capiche?



Office 365 is Dope Yo.  Sure you can have 150 POP3 accounts for $5 a month. But what is your time and data worth?  This platform offers KILLER value and a lot of folks are going to be transitioning (at least email) to it.

And you just know Microsoft will continue to enhance/add value to the platform…