Gmail blogged about their latest unsubscribe enhancements to mail viewed in the web client last week. Here at Bronto, I’ve been watching this development very carefully. I even blogged about it at deliverability.com.
To break it down, Gmail has two advertised methods by which an email recipient can let you, as a sender, know their intention to unsubscribe with Gmail as a proxy.
Option 1: If the sender is DKIM compliant and uses a special header for list unsubscribes to go to an email address (which Bronto automatically does), Gmail will add an unsubscribe link to the message details.
This is what an actual message looks like when it meets the above criteria. 
If you select “Unsubscribe from this sender” an email is fired off from Gmail to the address specified by the outbound email headers automatically. Ideally, the ESP or email platform that originated the message will receive this notice from Gmail and unsubscribe the user.
Option 2: The second option is a bit more elusive, but I finally caught up with it in action! The key here is to have an email sent with a reputation that fits Gmail’s proprietary “good reputation” threshold, along with the email being DKIM compliant and having a special unsubscribe header. Basically, you must do everything for option 1 above plus meet some metric within Gmail.
If a recipient marks a message as spam that meets the above criteria, s/he is presented with a dialog box that offers them the option of unsubscribing and marking as spam. This ensures that, again, an email is fired off from Gmail if the recipient selects this and the ESP or email platform immediately opts the user out after receipt of this notice. Until Gmail rolls out a feedback loop, this is the closest we will get to having an automated way to remove complainers from the email lists. 
As an aside, I also blogged about Gmail’s usage of the new “anti phishing key” they rolled out. Gmail has been busy lately! I managed to see this in action today when testing the unsubscribe functionality.
Check it out:
Chris Wheeler
Director of Deliverabilty at Bronto
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Our List-Unsubscribe Header includes BOTH a mailto: option and a URL … and we are not seeing the Option 1 nor Option 2 coming through.
Do you think this is not showing up because we have both a mailto: option and a URL in our List-Unsubscribe Header?
Thanks,
Carol
Hi Carol,
I would suggest testing a message without the URL unsub option in the List-Unsubscribe header. Send it to a Gmail account and see if option #1 comes up in the message details tab. If so, then it looks like Gmail hasn’t built support around including both and you might want to drop the URL altogether (do a cost/benefit analysis of those who currently unsub via Hotmail or other ISPs supporting the URL though). Perhaps you could change the headers to only include the mailto: piece when sending to gmail.com recipients?
About #2, this one is hard to reproduce (at least right now). It hinges on the internal reputation at Gmail of the sender being high enough. Personally, I think it’s a bit arbitrary based on testing I’ve done but then again, I don’t have any visibility into Gmail’s secret sauce around what threshold they’re using.
Hope that helps.
-Chris
When we tested for Option 1, we saw that we had to remove the URL unsub option in the List-Unsubscribe header to cause this to work correctly.
Thank you for your help!
-Carol
I was asked if I wanted to have Gmail,in the process of trying to find out what it was- I wiped out my original network. My address book is gone, everything. Now I cant locate my gmail account and want to get rid of Gmail and all that is associated with it. My email address is as follows; Rodawn @netins.net. Email me a phone number where I can talk to someone who can tell me what is going on. I am very unhappy!!
Thank you Rod Gabrielson
Hi Chris,
This is great information, thank you. I just want to suggest one modification regarding the DKIM authentication requirement. I believe the mail just has to be authenticated and that can be done using SPF and/or DKIM.
Best regards,
Mark