why no one should use hotmail,ever

Having worked with several online businesses that communicate with customers almost exclusively via email, I tend to be concerned about the reliability of the various email services.

The following is a true story, one that will hopefully teach others the futility of trying to work with Hotmail/MSN.

Part 1 - The Reasonable Request
I emailed Hotmail tech support, and explained that emails from my server were being placed in the Junk folder. This was in spite of

* the emails being sent only to customers that had placed an order, and
* the server only sending maybe 50 emails per month to the Hotmail domain.

I received a reply in fairly short order. It touched largely on two points:

* They recommended paying 100s of dollars per year to become a certified sender, which theoretically bypasses all spam filtering.
* They suggested that the emails were failing an SPF check (X-SID-Result: TempError), and that we should go to Microsoft's SenderID page for more details.

Part 2 - The Analysis
I had set up SPF for this domain YEARS ago, but of course was not certain that there wasn't something wrong with the configuration. Following the Microsoft advice, I went to the Port25 Solutions test page and performed some tests: Passed. Doubled checked with DNS Stuff to be sure: Another pass.

Part 3 - Please Sir, Help Me to Understand the Problem
Another email to tech support: "What can I do to fix my SPF problem? The tool you directed me to didn't have any suggestions."

Response: "Yes, your SPF record looks fine. We will ensure that the SPF record is up to date on our end and get back to you."

WTF?! You maintain a cache of stale SPF records? Don't ask, just be thankful they are helping...

Part 4 - A Week Passes, With No Improvement
Yet another email: "What's up guys?"

Rather Snarky Response (from someone different): "Representative X said he will look into it and he will reply when he replies. Further more, we make no guarantees of email delivery. And really, you should just be forking over the cash to SenderScore to ensure delivery."

Here and Now
I never received a response from Representative X, and all the emails are still junked, causing many customer service complaints.

Thanks Hotmail!