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I'm in the unenviable situation of being asked to migrate a mail server from Exchange 5.5 to Exchange 2010. The domain has two sites connected via T1 and an exchange 5.5 server (neither are installed on DCs). I know there is no direct path from 5.5 to 2010 so I've been working on trying to migrate to an Exchange 2003 VM first before migrating to 2010, but it's been hellish.

The domain only has about 150 users, I'm wondering if it's worth it to fight through this or to simply stand up a new mail server and manually recreate accounts, public folders, and calendars. Maybe, I can even export the calendars and recreate them, since they're fairly important. If I can convince the users to backup their entire mail box to PSTs, I think I can add them to a configuration in Postini that will push their mail to the new exchange server. I feel if we do this in small batches it won't be a complete disaster. Anyone have any thoughts on this? I'm not married to the idea, so I was hoping someone would be willing to either poke holes in it or give me some extra information with which to work. Thanks.

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2 Answers 2

In short, there is no way I would start from scratch....it would probably end up being more work in the long run. You will also have too many little issues, like things with free/busy data, not being right. Other things, like when people reply to existing e-mails, won't work. Depending on the attitudes and political power of the users, you will potentially have a lot of grumbling. That said, I have done the migration from 5.5 to 2003 many times, and 2003 to 2007/2010 many times, so it is not a big deal to me.

You might be better off trying to force your company to hire an outside consultant to do at least portions of the migration...like 5.5 to 2003 especially. Maybe you can do the second half? Or all of it even. After all, they are the ones, who put it off, and now it is already less familiar technology.

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I also would not start from scratch. I would suggest looking at the quest migration tools for exchange. The web page states you can go from 5.5 to 2007, but I think you can go to 2010 directly. If not it's certainly easier to migrate from a temporary 2007 install to 2010 than from 2003 to 2010. As another option I'd look into migrate to office 365, or exchange hosted services with so few users it might make more sense. (and it sounds like the have postini so they are already used to having their mail stored online)

If you decide to to the route of exporting the mail to PST files, I think your idea of moving users in batches is on the right track.

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