The Joel on Software Discussion Group

Ok so gmail added the "Send from other email accounts using gmail" feature a month or two ago.  To add an account to google, you have to verify you own the account...they send you an email to test it.  Ok so here I am hapily using the feature, joyed that I can use gmail to send emails with my business email address.  Then I just found out that people are receiving all the emails I send like this:

From:  secret.gmail.account.i.only.give.to.friends@gmail.com On Behalf of business.email@bizdomain.com

Are you kidding me google?  You've been giving out my private gmail address and generally making my emails look bizarre without really indicating it?  Why would i use this feature if this is what it was going to do?  On the compose screen it just says "send as: x@y.com"

I agree that is really stupid if that is the way it looks.  Why didn't you test it before mailing the world.

Sounds like you made some assumptions that bit you in the rear.

I suppose so... it's not THAT big of a deal, but it certainly makes the feature completely useless.

Yeah, I just tried it and I'll admit that the way its presented inside Gmail definitely gives the impression that it won't look like it came from Gmail.  I don't see what is supposed to be useful about it the way it works.

Because the information within the headers will identify the message as coming from a gmail server, if the "from" line is _not_ from a gmail address some systems will reject the message as spam.  Perhaps Google is trying to avoid that on your behalf.  Naturally, though, they should give you a choice or a warning or something.

I'll note that Yahoo Mail has the same feature, and puts the specified external address as your "from" line, not your Yahoo address.  Reading the headers makes it clear that it actually came from Yahoo, but doesn't reveal the Yahoo address.

I've not tried the gmail version; do they make you verify the address (by sending that address a code and having you enter it) as Yahoo does?

Well, I've been 'sending as' for awhile now assuming it worked as Phil did (and really that is the way Google presents it).

I did test it, by sending an email to another address and then fetching that with Outlook. Outlook shows only the from address without the gmail address.

When you check the Internet headers though, you see:

From: Jeff Barton <xxxxxxxx@mydomain.com>
Sender: xxxxxxxxx@gmail.com

For me, this is okay. If a mail client wants to add the "on behalf of thing", I don't care to much. But I agree Google should have been a little more informative on how it would be sent.

In Gmail, during the process of adding a send-as address, it sent a confirmation email to my other account.  That email had a numeric code which I pasted into the Gmail setup form I still had open.  There was also a coded link in that email which I clicked on and Gmail said I was now confirmed.  I don't know if the link and the code were part of a two-part verification, or if it was either/or.

I'm curious if it always worked this way or if it originally did what you thought and what it implied it would do and then they had to change it to avoid breaking cloaking/spamming rules.

The cloaked email address was a great feature that used to be very useful until it was broken by spammers. I agree that the way the feature works now it is less than worthless because not only does it not do what it advertises, but it actually does harm by sending spammy looking emails on your behalf.

My test showed the same thing Phil complained about.  From Outlook 2003 the To: field said "<myaddress>@gmail.com; on behalf of; My Name [me@otherdomain.com]

I can certainly understand if they have to do it for spam evasion (I'm an Exchange administrator now in addition to my dev duties), but my feeling is that if you have to do that to avoid spam filters, it renders the feature pointless.

"My test showed the same thing Phil complained about.  From Outlook 2003 the To: field said "<myaddress>@gmail.com; on behalf of; My Name [me@otherdomain.com]"

By any chance, are you guys sending this testing message to the same email as your intended from message? I'm also using Outlook 2003, and I can't duplicate your behavior. If I open the message and then click 'View'>'Options' and examine the internet headers, I can see the "Sender" address, but I am not getting a "on behalf of" message in the from field...

Beats me, I do remember testing this now... sent to an email address I checked with PINE, and it appeared as i expected.  I only discovered this "on behalf of" business when i noticed the content of my email quoted by a customer.

Gee, I'm kind of suprised anyone would have thought this would have "cloaked" anything except through obscurity. My sister or father ... but readers of JOS ?? odd

I happen to use a Perl module whose effect is just what you described. I have many boxes send to a user on one box, using .forward file I pipe into this Perl module, I log, then resend and in Outlook I get the From "box where resend is happening" On behalf of "box which sent it originally" and I like that.

No one can truly control how some client is going to render headers.

I was surprised by this too. The From address is what you set it to, but an extra Sender header is added with your gmail address. Like others, I guess this is to pass SPF anti-spam filters.

It's always been like this. The receiving mail client determines how the Sender headers appears to the recipient. To my mind, Outlook is wrong to display the Sender header in the From panel.

It is not brokenware. It is Outlook has exactly the same features.

If you give someone permissions to your email account, they can send emails from 'you'. Outlook will however show the email as send by THEM on behalf of YOU.