Exchange in the cloud

A few days ago, I came home and turned on my iPod Touch to check email. It said it couldn’t connect to the Exchange server. I went to a computer running Outlook and tried to log on. No dice. I pulled up a remote console window to see what was going on with the Exchange server. There were a slew of messages in the error log, all complaining about transient errors. I rebooted the server. When it came up, active directory was broken (more on that in another post). I decided to look at hosted Exchange.

Let’s back up a little. About 10 years ago I started running my own Exchange server. I did it for two reasons. First, my wife and I wanted to see each others Outlook calendars. Second, I wanted to be able to synchronize all of my mail clients. The installation was relatively pain free, and I discovered unforeseen advantages of client synchronization as time went by. One of my favorites was to be able to go on the road with my laptop and have access to all of the email messages that I would’ve been able to see back home. When I did get home and synched with the Exchange server, all the road messages were visible to all of the workstations.

I set up Exchange in an unusual way. It had no direct connection to the Internet, and thus could not directly receive e-mail. I did this to maximize safety; I operate the server in a set-and-forget fashion, and I didn’t want to take the chance that an intrusion could go unnoticed for a long time. I set up the Outlook clients to connect to the outside mail servers using a POP3 connection, download the data into Outlook and then upload it to the Exchange server. Having no direct connection between the Exchange server and Internet left me without Exchange web access, but I was OK with that, as I had Outlook on my laptop.

This worked fine for years. I found Exchange 2000 to be relatively easy to maintain. It wasn’t easy to get backups without shutting down the Exchange server, but each of the Outlook clients had a backup copy of the database. There are some third party products that allow you to back up a running Exchange server, but they’re not cheap; I didn’t bother.

About 18 months ago, I bought a new server. It came with then-six-months-old Windows 2008 Server. I got the 64 bit version of the OS, and bought a copy of Exchange 2007, which only runs on 64 bit operating systems. Windows 2008 server proved to be a much more complicated product than Windows 2000 Server, and the migration did not go smoothly. I ended up having to configure some things from scratch. In retrospect, it actually would’ve been simpler to start afresh.

I was not able to transfer the Exchange 2000 database to the new Exchange server. I had to export the database from the Outlook clients as PST files, create a new profile, and import the PST file.

All in all, the experience left me somewhat sour on running an Exchange 2007 server.

Last fall I hurt my back. During several days of enforced idleness, spent mostly with a laptop balanced on my chest, I explored some options for remote hosting of sophisticated mail services. There seemed to be two options: stay with Exchange and find somebody to host it, or go with Google Apps.

I concentrated on having either Microsoft or Google do the hosting. There were advantages and disadvantages to each approach.

• Exchange is by far the more mature product.
• Exchange supports tasks and Google Apps does not.
• The Google Apps Outlook plug in did not support all the versions of Outlook that I was running.
• The Microsoft-hosted Exchange server didn’t support all those versions of Outlook.
• Google Apps is somewhat cheaper.
• Google offers minimal support.
• Microsoft wouldn’t return my calls after they found out that I was only talking about a handful of mailboxes.

In October, I decided to wait. However, my newly-inoperative Exchange server made going for a hosted approach much more attractive.

I decided that I wanted minimal change. That meant finding somebody who was hosting Exchange 2007. I wanted somebody who would provide real support. Those two things meant that I was looking at third party Exchange hosting providers. There are a ton of companies that do that. I did some research on the web and came up with two names: Intermedia and Rackspace.

I called up Intermedia, and described my configuration, with special attention to the way I was pulling down all my messages into Outlook and pushing them back up to Exchange. The sales rep said that method wouldn’t work with their system, and that I would have to have all my mail sent to their server by changing MX records for all my mailbox domains to point to them. He also said that they’d charge me a new mailbox fee for each email address. I doubted that the way I was using Outlook would actually be a problem, since you’d have to work to defeat that capability in Exchange, but the rep was absolutely unequivocal.

So I called Rackspace. The sales rep didn’t think the way I was using Outlook would work, but she wasn’t sure, and said I could go ahead and try it. I decided to do just that. I signed up over the web, and my account was immediately live. I picked a domain I had sitting around idle, logged on to Network Solutions, and added MX records to point to Rackspace’s Exchange server. I wasn’t planning on getting much mail that way, but it was part of their recommended configuration. I didn’t bother waiting for the MX records to propagate, and got busy setting up my first Exchange client.

I exported the Outlook database as a pst file. I created a new profile with only one mail server, Rackspace’s Exchange server. I got some error messages not covered in Rackspace’s documentation. Rackspace offers chat window support. I used it to contact a tech, who explained how to click through the error message windows. After that, Outlook was able to log onto the server. I pointed a browser window at the web interface for Rackspace’s Exchange server, and logged on that way, too. I imported the pst file with the Outlook database, and manually refreshed the web interface Exchange window until I could see the email, contacts, calendar entries, etc. were uploading. I went away for an hour or so to let the synching finish. Then I added POP3/SMTP mail clients to Outlook, sent some test messages, and used the Rackspace web mail interface and saw that they appeared on the Exchange server. So the configuration that the sales rep thought would be a problem worked fine. I’m guessing it would have been fine on Intermedia as well.

Setting up all the other clients that looked at that mailbox was similar, except I didn’t have to import the pst file, since the data was on Rackspace’s Exchange server, and the clients picked it up with their first synch.

While I was at it, I set up my iPod Touch to synch directly with the Rackspace Exchange server. Then I set up my wife’s mailbox and her clients. Total elapsed time for eight or nine clients; maybe eight hours. Result? It all works as well as local Exchange, except it takes a bit longer to synch.

Migration downsides

• You lose some of your auto complete e-mail addresses (Why not all of them? No idea.)
• You  lose the list of web sites that you’ve identified as safe.
• If you use local ActiveSync to synch with a PDA or phone, on Windows XP, you’ll have to delete your old Outlook partnership and create a new one. On Windows 7, that’s all taken care of by the operating system.
• Passwords for Exchange have to be entered manually. When your own Exchange server is running on your own Windows domain, Active Directory can use the fact that you’ve logged in to your computer to see that you shouldn’t have to enter your password again to access your Exchange mailbox. This doesn’t work with hosted Exchange, since the host computer is on a different Window domain. There is talk of a workaround, but I haven’t pursued it.

If you’re not using Exchange, Lotus Notes, or Google Apps, you might want to consider it. Having your email, your calendar, and your contacts available on any machine you use is really convenient. As a bonus, the web interfaces mean that you can gain access from almost any computer in the world.