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When I switched to Google apps for my personal email back in January 2008, my #1 wish list item was to:

* Fix the “on behalf of” issue. If you use multiple email addresses, gmail and google apps are easy to setup to receive those emails. But when you send out using those non gmail/google apps addresses, certain recipients – especially those using Outlook – will see a “on behalf of email@gmail.com” in the “From” field.

This past Thursday, Google announced that they had fixed this issue, by allowing you to send out from your domain’s smtp server, thus dropping the “on behalf of” portion.

This is good news 🙂

I’ve been using Mac Mail and Thunderbird for a while in conjunction with google apps, so after tweaking my settings, I decided to try a few days of just Google apps for all my email accounts. Here is what I learned:

The good:

• Love having just one single inbox
• The Archive button is even more useful for work emails since the volume of email for me is pretty insane on most days

The bad:

• The signature feature is pretty weak. You can’t set it per account, and you can’t have different versions. I did find this Firefox add-on, Black Canvas, that looks promising — but it doesn’t seem to work in google apps right now
• If you rely on the google built-in mail fetcher to retrieve email, you’ll be waiting 20-60 minutes for new email – which is a problem. The work around is to have your other accounts forward all you email to your main gmail or google apps account, that way it shows up instantly
• Address book issues. I haven’t sync’d my contacts with Google contacts yet, so finding an email address is a bit clunky. I have everything in my OS X address book sync’d nicely with my iPhone right now, so I haven’t gone down the Google contacts road yet — plus I’ve heard some stories of problems of late, so thinking I’ll wait a bit
• No Gravatar support, so i can’t see the avatar/photos of the people I’m emailing with. I tried my colleague Jon Fox’s greasemonkey script but it’s not working — could be again b/c I’m in google apps. Would be nice to see Google support the Gravatar service, and other avatar services, natively ( Google folks, feel free to contact me if you’d like to chat about this )

Wish List:

• While google apps email search rocks, I actually miss my desktop client search feature where as I type I see results. In general I think google could do a better job with search on email, such as having “did you mean” based on my index, and better snippet highlighting, as well as some kind of live results
• Native iPhone app. The safari/mobile web version is getting better, but you can’t top the speed of a native app right now

Search / Sync Tip:
If you’ve been using a desktop mail client via IMAP like Thunderbird for your other accounts, google apps/gmail won’t have any of your sent messages. I find that I’m often searching for emails that I’ve sent, so this was something I needed to address. What I’m testing right now is a way to copy my sent messages into google apps. I loaded up all my accounts and the google apps account via IMAP in Thunderbird, and then started copying my Sent Folder messages from my other accounts into my google apps sent-mail folder. So far it seems to be working, and syncing up nicely.

Conclusion:
Very promising so far. If I can get the signature issue sorted out I’d be happy and may switch to this setup for all email.

Testing:
I’m also testing out an interesting desktop/web hybrid app called Mailplane on my colleague Andy Peatling’s suggestion. Their tag line is “Mailplane brings Gmail to your Mac desktop”. I haven’t used it enough yet, but it integrates nicely with your OS X address book, growl for notifications, and in beta is gears/offline support as well as HTML signatures. Checkout their 2 minute video overview for a good summary.