We changed e-mail providers four times in less than two years and made multiple attempts with managed IMAP, Zimbra, and Gmail before we finally got it mostly right. It all started with Rackspace's managed IMAP, which was fine -- except there was no calendaring, and as we grew, so did the need for shared calendars.
We switched to Zimbra in late 2006. But it ate several people's calendars and contacts. And although the Zimbra team was fantastic in helping us with our problems, it was becoming a bit too much to deal with. So we went back to IMAP at Rackspace but kept Zimbra running.
Later on, Rackspace began offering hosted Microsoft Exchange. I had been through the hosted Exchange nightmare at another company and refused to get involved in that ordeal again. Plus, for an open source company, it's weird to depend on Microsoft.
Then, like a shining star came Google Apps for our domain. So we switched again. Our first test-drive with Google Apps was all well and good for the first few days. Everyone felt OK about using POP and the Gmail interface, and we were reasonably sure that it wouldn't eat calendars as Zimbra had. What could go wrong?
As it turned out, plenty could go wrong. This was before Gmail supported IMAP, and the POP implementation turned out to have a few very bizarre quirks, such as the fact that you couldn't POP down e-mail that you sent to yourself, including CCs. Messages would disappear into the ether. And user management was a total nightmare; we had something like 40 aliases for lists that had to be entered individually.
It took all of five minutes before our developers freaked out. So we flipped the switch back to Zimbra. Mail delivery was still way more important than calendars, and Zimbra had come out with a new version that synced better and had a slick new UI. But Gmail offered massive storage, and most of our team liked the interface, so the move back to Zimbra left some folks pining for Google. That's why when Google came out with Google Apps Premier Enterprise (GAPE), we gave that a whirl.
GAPE ended up working quite well -- except for a few quirks (surprised?), such as the fact that if you use IMAP, you get this weird "All mail" folder that seems to never stop syncing on many versions of Mac Mail. But GAPE met all our requirements, including integration with Salesforce.com. Despite the occasional missing e-mail, we were sold.
I learned that e-mail and calendaring applications are the most personal apps people use, and thus the most difficult to unlearn or change. Your needs here will be driven by more than functional requirements.
Why I'm doing it all again at my new company
In the end, our jump to the cloud was based on a desire to avoid expensive, cumbersome infrastructure. While using cloud services was not without its challenges, I can absolutely say that I would do it again. And in fact, I already have: I'm running my new company in a very similar way with minimal capital expenditure for hardware and reliance on a variety of trustworthy providers to manage everything.
Yes, the cloud requires you to give up some control to get benefits. But as far as I can tell, the positives far outweigh the negatives.
Read more about cloud computing in InfoWorld's Cloud Computing Channel.