Step 3: E-mail

The first step is a doozy.

Moving my e-mail to the cloud wouldn’t be nearly as hard if I only had to worry about my primary address (david@schrag.net). But although I am the only person here, I have a lot more e-mail addresses. First there are the aliases – dschrag@schrag.net, dave@schrag.net, and so on. Not a problem. Every hosted e-mail solution lets you add aliases to your primary address. But then I’ve got two other kinds of addresses:

  • Separate accounts, like the ones I use for support requests, alerts, and the like.
  • Public folders, like those I use to collect and archive messages from the numerous Yahoo! groups and other mailing lists I belong to.

Generating a list of all active e-mail addresses from Exchange requires a command line instruction or script. I chose to use a command I found at eggheadcafe (see the comment from Ben Hoffman):

csvde -r "(&(objectClass=*)(proxyaddresses=*))" –l
displayname,proxyaddresses -f c:\EmailAddrExport.txt

This created a text file with 51 (!!) rows. Imagine if I had a “real” company. (My text file parsing skills are a bit limited. I was able to import this list into Excel to make it readable and then manually inspected it to find all the addresses within, but I’m sure there are more elegant ways to do this.) Each row represented a unique account and public folder. Some of these were created solely for Exchange administration purposes, like OABVersion2@schrag.net, and others I had set up as tests of conference room reservations. I didn’t need to worry about porting these to the cloud.

I’ll be paying a recurring charge for each account I have hosted in the cloud, so I wanted to keep the total number of accounts down, using aliases – nicknames, in GoogleSpeak — whenever possible. I also wanted to make it easy to find the most important mail on my mobile phone, so I wanted to keep my primary e-mail address as clean as possible. I decided I needed 4 accounts:

  1. A primary account for messages that sent to me personally by other human beings.
  2. An account for messages directed to the help desk.
  3. An account to receive alerts from the servers and computers I manage.
  4. An account for all the mailing lists I belong to: newsletters, Yahoo groups, vendor announcements, and other computer-generated mail.

From the spreadsheet I’d created, I prepared a list of all the aliases I would need for each account.

At this point, I have to interrupt the narrative. Ordinarily at this point I would weigh my options and decide which of the many hosted e-mail providers best met my needs. But almost a year ago, while researching cloud computing solutions, I’d already gone through the process of creating a Google Apps Premier Edition account for my schrag.net domain. I decided I didn’t have the patience to start from scratch, so I’m sticking with Google to start. Icreated three additional Google Apps accounts.

Now that the accounts were created, I had to change my DNS records to direct my incoming e-mail to Google’s mail servers. To minimize risk during the transition, I set up dual delivery. This process takes only a few minutes to configure, but it can be a while before the rest of the world realizes you’ve done it. (Notifying the rest of the world is referred to as “propagation.”) Once I was confident that Google would be able to accept my incoming mail and send mail out from my domain, I switched the MX records at my DNS host. I will have to switch the MX records yet again if/when I choose to add the Postini Message Security and Discovery services to my Google Apps account.

As it turned out, one of the most time-consuming part of this process was doing some spring cleaning that had nothing directly to do with the move to the cloud. As I thought more about which of my mail accounts were receiving what messages, I realized it was time for me to unsubscribe to a lot of newsletters, change some subscriptions from one address to another, and so on. This process will likely continue for a few weeks.

I made the switch a few days ago and the e-mail piece went pretty seamlessly. I’ve found I actually prefer reading my mail through the Gmail interface rather than through Outlook. (I can, however, continue to use Outlook to access my mail by setting up an IMAP account.) Importing my calendar items was a breeze, using Google’s sync tools. Dealing with my contacts has proven to be more of a challenge, and one I’ll cover in a different page or post.

Next step: getting rid of server-based antivirus.

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