Let me just start by saying, if you sent me email between 10pm 2/12 and 10am 2/22 and haven’t heard back from me, then please resend your message — I haven’t seen it.
On the eve of Google’s launch of Google Apps Premier Edition, I decided to migrate recursivefunction.com mail to Google Apps for Your Domain. Among other things, this allows me to use Gmail with an @recursivefunction.com address rather than an @gmail.com address. I’ve been using Thunderbird with POP for a while now, but need a more portable solution. IMAP seems too slow and still requires installation of an email client, while every web mail client I’ve seen pales in comparison to Gmail functionality. One of my clients setup their new domain with Google Apps, and the process seemed so smooth that I decided to finally jump on the bandwagon.
Here’s what I did wrong. And yes, I would’ve been able to avoid all of it if I’d just planned a little bit more — no need to rub it in 
1. Don’t start the migration at 10pm (or at least bring coffee if you do)
I naively thought it’d be a quick flip of the switch, and didn’t take into account how much time it would take to import my existing mail. I used Gmail Loader to move my saved messages from Thunderbird to Gmail. It worked great, but I had 10,000+ saved messages (3,000+ conversations) to migrate. It went very slowly since messages go out over an SMTP server one-by-one, and I had to re-label each batch to get it in the right “folder”. It took about 4-6 hours for this to transfer.
I think this really underscores the need for Google to create tools to let users move over their email. If I could have uploaded my 100 MB of mail and had that processed server-side by Google, the process would have been far less painful. I can’t even see most users (or IT departments) wanting to install a 3rd-party application to do this, not to speak of going through the migration process itself. And it’s completely out of the question for most people to start with an empty account or keep their old mail client around in case they need to look up old message.
2. Don’t change your MX record before importing your old mail
In my enthusiasm to get going I updated the domain’s MX record to point to Gmail before I started the process of importing my old mail. I probably wouldn’t have done this if I’d fully read the Gmail Loader documentation and saw this:
The timestamp in the inbox will be the time the message was received by Google. Inside the message the original date will be displayed.
What this means is that during the time it takes for all your mail to import you’ll also be receiving new email, and they’ll each go into your Inbox and appear with a current timestamp. I don’t think I got much new mail during that time, but it was hard to tell without having to open up the thousands of old messages that were streaming into my Inbox.
Google provides a temporary email address at a test-google-a.com domain for each account. I should have used this to import the mail first, and waited to change the MX record when I was ready to start accepting new mail on the account.
3. Don’t delete mailboxes from your old mail server
My old mail host has a feature/bug in their control panel where you can’t see mailboxes under a domain if that domain has custom MX records. So because I didn’t like the idea of the domain having mailboxes that were just sitting there forever, I decided to delete them right before I changed the MX records. This was my worst mistake. What happened as a result was that emails to me would bounce if they were sent through an ISP who had cached the domain’s DNS records. It probably took a few hours for most servers to start sending to the new MX address.
I should have reverted back and setup a catch-all address or else redirected mail to the temporary test-google-a.com address. But I was too tired to think that clearly.
–
It was painful, but I think it’ll be worth it. I’m still memorizing all the keyboard shortcuts and hacks to make Gmail as powerful as Thunderbird, but love it so far. The ability to label emails instead of being restricted to a traditional folder structure alone makes it far easier to organize messages.
Has anyone else given Apps for Your Domain a try? Or does anyone have any tips on seamlessly migrating mail to Gmail from a desktop client?
8 responses so far ↓
1 Doug Karr // Feb 22, 2007 at 10:28 pm
Ouch
2 brock // Feb 22, 2007 at 10:32 pm
Wow. What an ordeal. I set up brockrumer.com to use google apps for domains and I fwd’d my main address to my gmail address. Ironically I have been meaning to ask you about the best config. Now I’m just using gmail POP - seems easier than the hassle of apps for domains.
I like gmail, but I’ve only recenly found the freedom of letting go of labels. I was excited about tagging mail, but I was looking at it as being able to keep things in multiple folders. But why do you folder things? Maybe to satisfy a need to organize, but probably to find them later. But the power of google means you can free yourself of the chore of tagging. When you are looking for an email you know more than enough info to allow a search to get you closer to the email you seek than a “folder” ever would. I only use folders for subscriptions that I want to keep out of my inbox.
I still use it as my primary mail client, but I’m dissapointed in gmail - it’s dreadfully ugly, and due for some serious upgrades. Most of all I am very dissapointed at the lack of integration in Google’s whole suite of tools. If I could start a notebook and then turn it in to a doc or attach it to a calender item the world would be a fundamentally different place. This is the problem with Google’s independant innovation model.
Oh, and if you want to see webmail the way it should be, check out the Yahoo! mail beta. There are also some very nice AJAX-y webmail clients if you are willing to drop money, but who wants to pay for anything anymore?
3 Ed Illig // Feb 23, 2007 at 9:57 am
Very timely. We’ve been looking at making the switch office-wide. This banter is excellent fodder for our planning discussions. Thanks. We use electricwebmail and are less than pleased by frequent outages and paying for lesser services.
4 ade // Feb 23, 2007 at 10:10 am
I think my use of labels will evolve, but right now I have labels roughly for each decent sized project I work on. That’s helpful especially if there are multiple people involved so I don’t have to search on a number of different terms/senders. But I do have a lot of un-labeled mail (in Thunderbird it all just went into a massive “Work” folder or “Personal” folder) and it’s far easier to deal with that using Gmail’s search than what Thunderbird has. It also seems much faster too, which doesn’t make sense at first since you’d think there’d be an advantage to using 100% of my local CPU power.
It’s interesting to hear your discontent with the gmail UI. I do think there’s room for improvements, but I overall I love it. There are a lot of details that make it viable for a “power user” like myself. Yes their suite of tools could integrate better, but I think that’ll only improve over time. Besides, I’m using them anyway more so than my equivalent desktop apps.
I have a Yahoo mail account and have used the beta (mostly just to delete spam though), but I don’t like it as much as Gmail. It seems a lot slower, and I think it tries too much to act like a traditional desktop client versus Gmail whose interface (IMHO) seems more evolved.
Certainly a lot of room for debate here….
5 brock // Feb 23, 2007 at 10:31 am
One of my coworkers rails against the gmail UI any time it is mentioned, which may have tainted my comments. I’d like it to be better, but I find a tremendous net gain to using it. I went to using the web as my primary mail client w/ IMAP to keep things synced up with Entourage on my Mac, but I gave up on that. The age of the desktop app is over (at least for mail, contacts, and calendaring)
I do think there is a disconnect between gmail and the models comfortable to most peopel. It certainly resonates more with the tech crowd, but I don’t see that as a problem. If we expected one application to meet the needs of every person; we’d be foolish and we’d be out of a job.
My big problem w/ yahoo is that from my reading you have to transfer your whole domain to them, you can’t just do the MX. I just wasn’t comfortable with that - although I’m not sure I really have reason not to be.
For ed, here are some things I found when investigating web mail options:
http://www.zimbra.com/index.html
http://www.scalix.com/enterprise/
http://atmail.com
The open-source RoundCube project seemed to have a lot of promise, but it’s moving waaaay too slow for me.
6 ade // Feb 23, 2007 at 10:36 am
@Ed: I’d be surprised if electricwebmail isn’t bleeding customers because of newer offerings like Google’s. You might also want to check out Zimbra, which has received a lot of good buzz.
I definitely could see a lot of benefits to a company the size of Brainstorm using one of these suites.
7 links for 2007-02-23 | On Influence and Automation // Feb 23, 2007 at 4:57 pm
[...] Ade in Business » Blog Archive » How not to migrate to Gmail Let me just start by saying, if you sent me email between 10pm 2/12 and 10am 2/22 and haven’t heard back from me, then please resend your message — I haven’t seen it. (tags: gmail googleapps) [...]
8 Ade in Business » Blog Archive » I found another way to break my email // Mar 3, 2007 at 9:59 am
[...] wasn’t enough that I broke my email for a few hours last week with the Gmail migration. I woke up this morning to the curiosity of 0 new messages in my Inbox — no spam, no cron job [...]
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