Hotmail must die

Hello blogosphere!

Today’s adventures in How-The-World-Sucks is brought to you by Microsoft, the evil-doers of the computer world. The latest example of how corporate greed is destroying America came across my plate after a few friends, who use Hotmail for their email provider, mentioned that they were not receiving email from me. Given that this was multiple people, I figured that there might be something wrong with my email setup. I just so happen to have a Hotmail account (that I never use) and I used that for my testing. Once I started poking around, here’s the evidence that I gathered:

  • Email sent from my personal domain would not be delivered to email addresses. However, I could reply to email messages that originated from, just not send new email to Hotmail.
  • Email sent from my work (a domain I help administer) to email addresses would go through, but it would take upwards of 3 hours for email to come through, and they would appear in my Junk folder, marked as spam.
  • Email sent from my Gmail account would go through immediately.
  • Email sent from several domains run by friends of mine would either never get delivered, or would take ages and ages and then finally appear in my Junk folder.

Weird. According to my mail server logs, and those at work, the email messages destined for addresses were delivered to Hotmail’s servers without any errors, and according to the SMTP protocol Hotmail is then required to either deliver the email, or bounce it back (neither was happening). Now, in today’s spam-filled world this is not always the case, so I was going to give Hotmail the benefit of the doubt for now, and try to figure out what was going wrong. I started poking around on the net, and found zillions of references to people that were having awful problems with mail delivery to Hotmail. Some mentioned issues with Microsoft’s implementation of SPF SPF, so I removed my entries from DNS, with no change in functionality (yes, I waited for DNS caching to time out). Some mentioned spam filtering issues on Hotmail’s end, the only solution to which seems to be paying a 3rd-party corporation $1400 and up, per year, to be whitelisted by Hotmail. Uh, no thanks.

Then, I stumbled across a grammatically awkward but information-rich post by an administrator who ran into similar problems. His post made me try a few things:

  • I sent email from work to my address using Outlook and it went through immediately.
  • I then configured Thunderbird, my email reading program, to set the User-Agent header to read “Microsoft Office Outlook 11″, and sent email from work to my Hotmail account, and this went through immediately. However, email sent from home with this trick did not work- email would still not be delivered.
  • I then configured Postfix, which I use as my email server, to remove any User-Agent header, as well as inserting X-Mailer: Microsoft Office Outlook 11 as a header (which is what Outlook does). This seemed to be the magic fix, as email sent from my personal domain would now go through immediately.

Wow. In my professional opinion, this clearly says that Microsoft is going way out of its way to make people using open source software suffer when dealing with people that use Hotmail. Just another way in which Microsoft is trying to eliminate competition for its market, not by innovating and producing good products, but by using their market share to fight dirty. Who suffers from this? We do. The people out there on the streets. Corporate greed at its finest.

The net result? Well, I strongly encourage everybody out there that has a Hotmail account to immediately switch to another provider. Gmail and FastMail, among others, would be good choices. In the meantime, I will keep my domain configured to fool Hotmail into thinking I’m a nice little Microsoft drone, using its crappy products, so that I can send email to my friends. That is, until they all switch to a better email provider. :)


ps- For those of you out there using Postfix, here are the lines I added to my header_checks file to remove the User-Agent header and add in the Outlook header:

/^User-Agent:/ IGNORE
/^To:.* PREPEND X-Mailer: Microsoft Office Outlook 11

About lackhead

"I tell you, we are here on Earth to fart around, and don't let anybody tell you different." -- Kurt Vonnegut
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One Response to Hotmail must die

  1. Pingback: » Hotmail must die, take #2

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