How To Migrate Messages Using Outlook for Mac 2011

Ben Greiner -

We've been recently spent a lot of time in Outlook for Mac 2011 and our experience has NOT been good.

  • We can't move entire folders from one mail server to another
  • We can't select multiple folders using either the Shift or Command keys
  • It's frustrating to perform a simple task like rename a folder because any progress (sending, receiving, updating) that takes place in Outlook during the renaming process will kick you out of the folder and you'll be forced to try again.
  • Outlook is just plain slow compared to Apple Mail.
It's little stuff but it amounts to a HUGE pain when trying to migrate an Outlook user from one IMAP mail server to another -- especially a user with a lot of folders, and subfolders.

Here's a workflow we've developed, that is far from ideal but seems to get the job done most consistently, efficiently and with the least amount of errors.

  1. Confirm the following in Outlook > Preferences > Accounts > Source IMAP Account > Advanced > Server 
    • CHECK: Always download complete messages bodies
    • UNCHECK: In Inbox only
  2. Check for missing IMAP folders: Outlook 2011 for Mac - Missing IMAP Folders
  3. Drag and drop individual folders from Outlook to a folder on the desktop. (See Step 2 in How To Archive & Restore Email from Outlook 2011 for Mac for details.) Be sure to copy the top-most folder and any subfolders because just copying the top folder will not copy any of the subfolders. Also, empty folders will not copy so you'll need to manually create these if needed. It's faster to crete them in Apple Mail than in Outlook.
  4. Setup your new IMAP account in Apple Mail. Within Mail choose File > Import Mailboxes > Files in mbox format > and choose the folder from your desktop with the Outlook mbox folders. Confirm and Continue, then Done (when the import completes).
  5. Now drag and drop the folders from the newly created Mail Import folder "ON MY MAC" to the new IMAP account. Unlike in Outlook, you can drag and drop multiple folders at once. Although the rule still applies that if the copy fails try moving only a few folders at a time. If you have subfolders, then drag the top-most folder first, followed by the sub-folders.
  6. Once the folder move is complete, go back to Outlook and compare the number of messages in each folder between the original account and the new account to ensure nothing is missing. To be extra safe, rename the original folders, "MOVED -  Original Name" rather than deleting them.

One downside to this process is that all migrated mail will arrive as "unread". You plan to read them all again at some point, right? That's why you're saving them. :) In Apple Mail you can select a folder, right-click and choose to Mark All Messages as Read.
At this point you are done. You can either remain in Mail and ditch Outlook (recommended) or go back to Outlook and setup your new IMAP account. All your old messages and folder structures will be available. Hooray!

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