Tuesday, April 1, 2008

Avoid gmail's "on behalf of" problem

The issue: gmail offers a way to send e-mail through their web, pop or imap interface so that it's supposed to appear that it was sent from another account you own and aggregate into gmail for storage. However, in strict keeping to standards, gmail sends out BOTH addresses, so some clients show a from: tag like "From abc@gmail.com ON BEHALF OF abc@xyz.com".

I HAVE FOUND A SOLUTION FOR THIS PROBLEM, however it requires you to use Microsoft Outlook 2007 as your client (or another client I'm not aware of that allows you to redirect where your sent messages are saved).

-Tell gmail to check your other e-mail address via POP (just follow gmail's directions).
-Don't use outlook to check your other e-mail address via POP.
-Enable IMAP access for your gmail account (Settings->Forwarding->Enable IMAP) in the gmail web interface.
-Set up Outlook 2007 as follows:
Incoming Mail Server: imap.gmail.com (just like gmail tells you to)
Outgoing Mail Server: [put here whatever your other e-mail provider tells you to use for POP clients...something like smtp.xyz.com usually]
Logon User Name: [your gmail address] (just like gmail tells you to)
Logon Password: [your gmail password] (just like gmail tells you to)
Outgoing server requires authentication: Log on using: [your POP credentials for your other e-mail provider...usually just your other e-mail address and password]
Incoming server port: 993 (just like gmail tells you to)
Outgoing server port: [whatever your other e-mail provider tells you to use].
-Now, once you're connected to gmail and have synced the folders, go back into Account Settings, and "Change" your gmail account. Click the "More Settings ..." button, and under the "Folders" tab, tell it to save your sent items for this account in [Gmail]\Sent Mail.

What this all does:
You're actually sending the e-mail straight through your 'normal' pop server directly from Outlook. It's not looping through gmail at all, so there's NO way that the recipient of your message could glean your gmail address from that sent message. However, once the message is sent, Outlook posts the sent message to gmail's Sent Mail folder via IMAP. Thus, the message gets synced up to gmail as if you'd sent it straight from gmail.

So then when your recipient replies back to you, it goes back to your other e-mail address, which you're having gmail gather messages from. Outlook will get their reply via IMAP from gmail. If you reply to them again, it's likely that gmail's servers will be shown in the message headers, but I don't believe your actual gmail address is shown in any way (I may be wrong). But still, they'd have to dig through the message headers for it; there are no common user-viewable fields that gmail.com would show up in. In gmail's web interface, you'll still see the 'conversations' linked together, just as if you were sending from gmail.

Note that I didn't tell you to allow gmail to send using your other (POP) account...for this to work, your messages MUST be sent from Outlook (or another imap client that can save sent messages in Gmail's custom folder path). If you send a message from gmail's web interface, you'll be sending from your @gmail.com address. Though you'll still see those sent messages show up in the "[Gmail]\Sent Mail" folder in Outlook, that's probably not exactly what you want. Best case, your recipient's email clients will again show "On behalf of" in the From: field on your message.

Still, this is the best solution I've found...nobody on the web that I can find has posted this method. Now if only Outlook would let me delete the "Junk E-mail" and "Sent Items" folders from imap accounts...these show up in gmail as available labels, and I haven't found any way to get rid of them. It'd sure be nice if gmail just sent messages straight through the pop servers you elect, just like a real e-mai client does...then you wouldn't need Outlook to do this, and you could just JUST the gmail web interface (which is, after all, quite nice).



At July 19, 2008 at 5:10 PM , Anonymous Anonymous said...

This works great for me. thanks for the tip.
Dave F.

At July 19, 2008 at 8:37 PM , Anonymous Anonymous said...

There's a discussion at http://www.macosxhints.com/comment.php?mode=view&cid=101057 that deals with this, and that has pointers to some solutions, both for the gmail "on behalf of" problem and a similar limitation in Apple's new MobileMe, which doesn't make it easy to send email from addresses other than @me.com addresses.

At September 7, 2009 at 4:21 AM , Anonymous Anonymous said...

Thanks for your article - though now GMAIL HAS TOTALLY SOLVED THE PROBLEM!




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