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Lessons learned from migrating to Office 365


My migration of staff email accounts from our onsite Exchange Server to Office 365 continues as I write this, though now at a somewhat quicker pace. With just under 50 mailboxes left to move, I should be done by the the end of this school term. So far the move has been mostly trouble free, with no email being lost. There have been some small incidents that have helped to shape future mailbox moves and have provided valuable lessons. In no order, here’s some of what I’ve learnt along the way:

  • If you plan to migrate your user’s existing mailboxes up to the cloud, you absolutely need a fast internet connection. 20Mbp/s minimum in both directions, but the faster the better.
  • If possible, get your users to perform mail cleanups before you move their mailbox. The less items in a mailbox, the less time it takes to move said mailbox into the cloud. There’s also less clutter for users after the move, which usually makes people happy, since less clutter is always a good thing.
  • If you are doing a staged migration, try to move as many mailboxes as you can per batch, so that you don’t draw the process out too long. The longer you run two systems, the more risk of something breaking or going wrong along the way.
  • Watch out for user accounts that have been renamed, i.e. people with surname changes. If this isn’t cleaned up properly before being synced to the cloud, it can come back to bite you in the ass. Cue frantic searching and entering arcane commands into Powershell.
  • Users don’t always appreciate or use manuals you may have written. Write a manual anyway, so that you’ve covered your ass.
  • Mailbox moves often don’t happen as fast as you think they should. Budget extra time for a large move.
  • Modern Outlook Web App is a really nice mail client. Light years from Exchange 2007 version obviously.
  • Use Office 2016 for fixed desktop users to connect to Exchange where possible. All previous versions are not going to get the same attention and support from Microsoft in case of trouble.
  • Office 2016 perpetual (i.e. the version you volume license and uses MSI installer) won’t get feature updates over its lifespan. This means no new and cool features like Focussed Inbox.
  • Some programs that interface with Outlook don’t like the 64 bit version of Office.
  • Direct users to the stand alone Outlook apps on Android and iOS. The built in mail client should connect with too much hassles, but Android and Exchange have always had a slightly rocky relationship in my view.

I’m in the process of moving the last giant mailboxes over in the coming week. Once that’s done, the pace of migration should go up as I move other users over with more “normal” size mailboxes. Once everyone has moved, it’s a case of testing to make sure everything is ok, then changing MX records to cut over for direct email delivery to the cloud and to cut out mail coming onsite and then back out again.

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  1. June 2, 2017 at 21:22
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