Lackhead.org

Hey blogosphere-

Just a quick update to an old article on Why Hotmail Must Die- today our mail servers at work got hit with the lovely Hammer ‘o Hotmail and all email from our domain to any Microsoft email server (hotmail.com, msn.com, MS Live, etc) is now being rejected. Not that it is exactly the same as the predicament I found myself in last year, but similar enough that I decided to play around and implement DKIM at home to see if that made any difference in deliverability from my domain to Hotmail. All testing was done with SPF records in place, FYI. Here are the results:

1. No DKIM, no rewriting of headers

   Result: email sent from my domain to hotmail.com addresses would just disappear…or if you were lucky would wind up in the Junk folder.

2. DKIM, no rewriting of headers

   Result: email sent from my domain to hotmail.com addresses would just disappear…or if you were lucky would wind up in the Junk folder.

3. DKIM/No DKIM, but postfix configured to nuke any User-Agent: header and to set the X-Mailer: header to read Microsoft Office Outlook 11

Result: email sent from my domain to hotmail.com addresses would arrive just fine.

So, what’s the conclusion my fine friends? Well, industry-standard anti-spam measures like SPF or DKIM seem to have no affect on mail delivery to hotmail.com address. However, telling Microsoft that I’m using their product seems to do the trick. Is there any doubt left that Microsoft’s main business model is bullying?

Somehow, I don’t think this is going to do the trick at work, but hey, it is at least worth a shot. If anything interesting pops up I’ll let y’all know.

-c