How to migrate almost half a million messages to Office 365 (without tears)

Back in March, I described my move from my regional Exchange hosting provider to Office 365. I explained why I chose Office 365 over Google Apps, my experiences with Microsoft's support, and even my ongoing dismay at the dismal quality of hold music customers are subjected to by cloud service providers. Here's the entire DIY-IT project page on that project.

But what I didn't do was tell you how I moved 20 some-odd gigabytes of email between the two Exchange providers. That's what this article is about.

Here was the scope of the problem. There were only two mailboxes: mine and my wife's. On the surface, that might seem like an easy migration. But we'd used our old hosting provider for over a decade and we get a lot of messages (and I get an absolutely mind-boggling amount of mail daily).

We'd also gotten into the habit of using our email as the "database of record" for everything we've done, from online purchases to the details of business relationships. As a result, we file everything in our various email folders, and delete little besides spam.

And we had all that, going back to 2002. All told, we had 480,000+ messages to move, along with all their associated attachments.

This is a non-trivial task. One way would be to go into Outlook, establish a connection with both services, and copy all the messages over, folder-by-folder. I've done this before, on a much smaller scale, and even on a much smaller scale, it's incredibly error-prone, Outlook doesn't play along with any degree of enthusiasm, and there are both transfer failures and corrupted messages.

It's ugly. I needed a better way.

And that's when I stumbled on YippeeMove. Yeah, the name alone almost put me off, but I needed a workable solution. And, believe it or not, that solution cost me $30 — $15 each for my wife's mailbox and mine.

I'll tell you this, the folks over at YippeeMove earned that thirty bucks, not even because they moved all my messages, but because I was an absolute Nervous Nellie during the transport process and I probably bugged them 20 times during the week of the move.

Let's talk about the details first. They can move from most email providers to most other email providers. The key is that both providers need to have an IMAP interface available.

What you do (and this, too, was a bit nerve-wracking) is you go to the YippeeMove Web site, log in, and enter your login details for both your source and destination email accounts. You enter in a few more details (no more than you'd need to connect to your email on a smartphone), and then kick off the job.

This is not a fast process. It took a little over a week for the messages to get from provider to provider. It is, however, a hands-off process. Once you click the "go" button, that's all you have to do. Take a week's vacation, and when you come back, your mail will have migrated over.

Of course, I couldn't leave it there. I had to check with them every few hours. Whenever I saw a slow-down in the message transfer rate, I had to ask them what was wrong. When I saw everything stop for a day, I bugged them incessantly, before eventually realizing I'd changed the password on the destination account in the middle of the transfer.

There are also security implications. You're giving you email account credentials to an unknown third-party company. On top of that, you're letting them see every email message you may have. Hmm... it strikes me that YippeeMove might be an ideal front for the NSA, Chinese hackers or the Russian mob.

I was, indeed, worried about this obvious security issue. I did change my login credentials on both sides as soon as the transfer was completed, but the fact remains that they did get to touch (and who knows what else?) all my historical email, going back a decade.

But I made a decision here. The decision was that I could either recruit some help, or I'd lose my historical email, because I never would have had the time to move 480K+ email messages on my own, by hand. I decided it was more important to retain the functionality of that archive, and — besides — my main email store didn't have all that much that's particularly confidential (my government email accounts are in completely separate systems).

It was a risk, it took a leap of faith, but it worked out fine. I was a nervous wreck during the entire transfer week, but now I look back on it and smile. The fact is, for all of thirty bucks, the service offered by YippeeMove (wacky name and security concerns notwithstanding) is a heck of a deal and worked out just fine.

Oh, and in the three months since the move was completed, I've seen absolutely no evidence that any of the data I moved was compromised in any way. The company seems completely to be just what it says it is — an email migration machine.

If you have to move a massive pile of email, YippeeMove is probably the best thirty bucks you'll ever spend.