October 31, 2009

Google Mail Weirdness

I'd be delighted if somebody could explain what the hell's going on here. I switched mail for the holdenweb.com domain to run through Google's Gmail for Domains service. Things had been going quite nicely, and the spam levels had reduced amazingly without me having to apply any external filtering (which makes me wonder just exactly why Google Groups is so clogged up with the output of asshole spammers, but that's another post).

Recently I have started to receive replies to emails sent out from my holdenweb.com account in the Gmail mailbox I have used for years. At first I though this might be Thunderbird (or me) getting my email accounts and personalities mixed up, but it appears this isn't the case. Here's a test message I sent to myself as an experiment, as it looks in my Sent folder:
So it definitely looks as though it went out from holdenweb.com. And here's the same message as it arrived in my Inbox:
So it goes out from my holdenweb.com address, and arrived at the recipient from my gmail.com address. That's pretty evil, Google - or is there some obvious way I am shooting myself in the foot? It's making my mail conversations pretty hard to track right now.


Ant... said...

I hit this same issue with my domain running through gmail. If you go into the gmail config, you can change the settings to use a different reply-to address.

It's not ideal, as the gmail account is still in the from header, but at least most mail clients recognise the reply-to, so mail comes back to the place it was sent from.

Carl Trachte said...

I think Michael Foorde had the same problem over at the ironpython.info domain - could be wrong. Someone had tweeted about this, so it's not just your domain or your account.
Carl T.

Vincent said...

I am not sure how you have it setup. If you are using holdenweb@gmail.com has your mail server then that is the problem, even if you add the email address steve@holdenweb.com to the account, and set it as your default address it always sends it with a not that it was sent via holdenweb@gmail.com. To fix this get a free google apps account google.com/a/
Then it will work like you want.

Steve said...

@Vincent: the holdenweb.com domain is served by Google Apps, which is precisely why I can't understand the behavior.

eMBe said...

AFAIK Gmail SMTP server replaces the From (and MAIL FROM:) with the address used during authorization. Mmaybe you are sending the mail using the SMTP configuration for your @gmail.com account?

Steve said...

@eMBe: I was indeed sending mail out through Gmail's SMPT server and authenticating as the other Gmail identity. Nailed it, thanks very much!

Kenneth said...

Your client is authenticating SMTP w/ your gmail credentials, rather than your Google Apps credentials.

Steve said...

Thanks, Kenneth. I take it you didn't read the other comments? Fixed this a couple of days ago (but you are right about the solution).