Google Apps and Gmail Fix “On behalf Of” Issue

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” 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.

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.

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.

14 thoughts on “Google Apps and Gmail Fix “On behalf Of” Issue

  1. Although it’s definitely not perfect, I save different signatures using the “Canned Responses” feature that’s available in Labs. Then I set my default signature to nothing (to avoid accidentally sending the wrong one, but you could also set it to basic personal details perhaps?) and just click to add a “canned signature” to my email before I send it. It’s like a permanent clipboard.

  2. I found using Canned Responses, Sender Time Zone and Forgotten Attachment Detector the most useful addons to use from the labs. Canned Responses for signatures as described by Beau. Sender Time Zone shows a small icon for daytime (phone) or night (email) based on the senders time zone and the Forgotten attachment detector lets you know when you mentioned attachment or similar in your mail but missed that attachment. I’m using contact and calendar sync with my iPhone. So far I did not have any issues, but never used the apple address book or iCal.

  3. I nearly leapt for joy when I first read about this on the gmail blog, but have had a difficult time implementing it for one of our company’s external domain email users because our domain host isn’t approving the connection. grrr

    PS great idea for using Canned Response for sigs. Ta!

  4. I understand that many setups would want to use their own mail server for outgoing. Unfortunately, I’m Admin for a couple organizations that are using Google Apps to offload services to the Cloud, and that defeats this purpose.

    Besides preventing you from offloading mail server work, this makes every message traverse extra hundreds of miles, and makes troubleshooting mail routing problems much more complex. Every damned routing problem that comes up, I have to multiply my work to see whethere the problem is to or from Google or my own mail servers.

  5. Ed says:

    I have all email consolidated to my one gmail account and forward all emails from my 4 domains that I owned to gmail.

    The on behalf is still very inconvenient. For example, if you host your domain on google app, and you created one account let’s call it admin, you can’t simply add nickname (or alias) to send as the nickname.

    I really hope that they would do this, if let’s say is an alias of, it should really send the email as using the as login for and never mention in the header.

    The problem right now is the receipient will see on behalf of

    To work around the problem, you will have to create an account per email address you want to send as from.

  6. john says:

    The signature issue can be tackled using Gmail’s “Canned Responses” feature. I just save a different canned response for each of my accounts (I have 8 addresses configured in my gmail account) and simply insert the appropriate response (or signature) when sending an email.

    The benefit of this feature is that I don’t have to rely on a browser plug-in, as it can be disappointing to lose it when upgrading to the next version.

    If you need more info, I’d be glad to send you a screenshot.


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