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Moving from SBS Exchange to Office 365

November 19, 2012

In order to keep the benefits of an Exchange Server and lose the complexity of Small Business Server I need to move to a cloud Exchange provider. At $4/month/user, and Microsoft standing behind it, Office 365 seemed to fit the bill.

My first attempts at migration met with failure. I could not get Office 365 to connect to my Exchange Server. Hours on the phone with Office 365 support yielded no solution. My strong suspicion was that some misconfiguration in SBS Exchange was the source of the problem. This was the complexity of SBS striking out at my from its position with one foot in the grave. Fortunately I had access to free MS technical support from Microsoft to assist in the migration.

Finally someone suggested simply exporting my 5 users’ accounts to a PST file, signing on to Office 365 and then importing that PST file. It was a kludge, but with only five users it was the path of least resistance.

This approach worked and I could finally cease using SBS Exchange. A few more Snafus lay in wait, however:

  • I discovered the hard way (not getting emai for a weekend) that I needed to change my users over to use our domain manually within Office 365. This does not happen automatically when configuring Office 365 to work with a user’s domain.
  • I needed to disable auto discover on my old SBS box so that clients could connect to Office 365 instead of the dead Exchange server.
  • I also needed to change a setting on the group I had created as a common email address for my wife and me so that emails from outside the organization could go to that address.

This would prove to be the hardest part of the move away from Small Business Server.

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