I migrated one of our SMB clients to O365 over the past week.  They were coming from a hosted POP3 environment and had a mixture of users that would be going to O365 E1 plans and some that were “phone only” P1 plans.  You would think it would be “easy” to migrate an organization like this, wouldn’t you?  Well, you’d be both right and wrong!  There are many things that can go wrong and many things you need to think about, here are a few things we learned along the way that can help you with your migration!

Pointing upThis one should be obvious … clean up your Outlook files!  I have lost count of the number of users that I have come across that have ridiculously messy Outlook – a gazillion items in their Inbox, just as many in the Deleted folder (I need to go back and look at stuff …), tonnes of old “crap” in their email (so gigabytes of email history).  The list goes on.  In order to have a clean migration up to O365 you want to limit the amount of data that you initially push up into O365 to something that is manageable.  As my customer was not saving anything in the hosted email system the user’s individual Outlook PST files were going to provide the historical data that they wanted to see in O365.  That is all well and good but you need to be sensible about what you migrate up into O365 and you need to be cognizant of the time it takes to migrate a volume of data.

In this case we were using Outlook to push up data to O365 after the users was connected to O365.  Outlook will take time to synchronize local data with O365 and vice versa.  You can use the PST import tool in O365 to perform much the same task but, either way, it will take time.  If you are under the gun you want user accounts “live” within O365 as quickly as possible so minimizing the amount of transferred data is a helpful first step.  Also, because Inbox and Deleted are special folders in Outlook and Exchange, the cleaner they are the better your chances of a successful migration.  Big, ugly Outlook profiles are a guarantee of possible migration problems!

Pointing up Use a third party tool like MigrationWiz to handle as much of the migration as possible (we used it for the “phone only” users that had a lot of data left in the hosted email system).  Microsoft’s provided O365 migration tools are “okay” but they are basic and leave lots to be desired.  The third-party tools that are on offer go a long way towards easing the task of migration.  They do not eliminate the possibility of issues during migration but they sure can reduce the overall work load!  A tool like MigWiz generally allows you to do trial runs and multiple passes so that you can find and fix potential migration problems.  And, of course, you probably still want to enlist the help of a Microsoft O365 partner to help you with the migration (hint, hint).

Pointing up If you are coming from a NON-EXCHANGE environment (like POP3) then you need to prep your users for the different way things will work on their phones (and possibly tablets) when they connect to O365.  This was the big challenge at my customer and, frankly, one I hadn’t really considered as I’m so used to customers having an Exchange environment.  The first thing that threw users was the simple fact that Outlook, phones and webmail were no all integrated and that what happens inside one “location” (Outlook, phone, webmail) was reflected almost immediately in the others.  One user made a habit of reading email on his phone then deleting it as he knew it would be in his Outlook in the office; he was shocked to find out that deleting it on the phone meant it was gone out of Outlook!  There were a few more “oopsies” along the way before users adjusted to the idea of how things work and it underlines the need to inform, prep and even train users on how things will work once you are moved on to O365.  In the case of my customer, the phone thing was far more “disruptive” than anything else during the migration and it was an eye-opener for me.  I was expecting problems from an Outlook perspective and there were none to speak of but the phone thing took a lot of handling, far more than I ever would have imagined!

UPDATE: You might want to consider the OWA app for iPhone and Android as it “containerizes” Outlook functions (email, calendar, contacts) within a single app and keeps that data completely separate from other email/calendar/contact info on the phone.  I discovered with my client that many users had a bunch of accounts set up on their phones and they were getting massively confused by the profusion of “stuff” on the phone.  OWA certainly made it clear what was what in terms of the “business” email and calendars and contacts.

Pointing up Check for “mail enabled” applications like accounting or other line-of-business applications.  You might run into issues with how the applications interact with O365 and Outlook.  This particular area has proven to be a challenge for a number of older mail-enabled apps (MAPI) although it is not insurmountable.  Relaying is less of a problem and can be easily configured inside O365 but you do have to follow the instructions properly (no cutting corners!).

UPDATE:  O365/Exchange Online sets a MAPI property on each user’s account (you can see it by looking at the user account in the O365 Management portal and selecting “Exchange Properties”; in those properties you will see MAPI and it is DISABLED by default.  If you have a user that uses MAPI-enabled apps you may find that enabling this setting for the user solves the problem.  In the case of the customer I referenced earlier it certainly fixed a problem with outbound email generated inside BusinessVision (SAGE) accounting.

And, again, don’t shy away from enlisting the help of a Microsoft O365 partner, specially one that has already performed a number of migrations.  O365 is a great platform but there is work involved with successfully migrating on to it.  It never hurts to leverage someone else’s knowledge and experience and that is doubly true for O365 migrations.

O365–Things you can do to help ensure a clean email migration
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