Hotmail – testing the limits of market power

Market power (scale, network effects, or other) allows an operationally inferior firm to sustain a position. To see see how powerful this effect is, consider that people are actually still using Hotmail.

Since April, everything I send to Hotmail is classified as spam. Everything. Even mail to myself. Hotmail then deletes all spam after only 5 days.

So, when I email any client at Hotmail, it goes to spam, 100%, even if we’ve corresponded for months. If he doesn’t check within 5 days, Hotmail deletes, and I can never prove delivery. This renders Hotmail unusable for business.

This problem occurs only at Hotmail. My domains and IPs are not blacklisted. I have never sent bulk mail. I send fewer than 20 messages per month to Hotmail, all to clients who have paid me in advance to deliver to them.

Is this really a problem with Microsoft? Consider what happens when you try to fix the problem.

First, set up Sender Policy Framework. This is good practice — I should have done so long ago. However, at Microsoft, due to the principal-agent problem in the marketing department, SPF is called “Sender ID.” It has no discernible difference from SPF other than the name.

Once Sender ID is configured, instructs you to notify Oops:
Remote host said: 550 5.1.1 User unknown

So they’ve shut down the Sender ID cache update address, and failed to document it on their own instructions page. Ominous.

Undaunted, I found the next noodle in this strategic spaghetti: MSN Smart Network Data Services. To proceed requires signing up for Windows Live (formerly MSN), which yields this:

From the user’s point of view, it looks like Windows Live is offline in the middle of a weekday. Actually, it’s yet another case of silent failure on incompatible browsers, a widespread Microsoft problem mentioned in previous posts.

No problem. Changed browsers. Got a Windows Live account. Went back to Smart Network Data Services, and was greeted with this:

So Microsoft’s email security site has a bad SSL certificate. It’s a security site. With a bad security certificate. Ah, what they hey, I’ll risk it. Set up SNDS, and all was done.

After all that, everything sent to Hotmail is still classified as spam. No change.

Just one option left, according to the MSN postmaster: “Sender Score Certified,” formerly “Bonded Sender,” formerly “Return Path.” Under this scheme, you can rent the right to send anything to Hotmail, for a fee of US$1,400. To send 10 messages a month. Right.

Fortunately, there is a much cheaper and simpler solution, for some reason not mentioned at the Hotmail support site: I can refuse to support Hotmail, and persuade clients to use a different email provider. This has been effective.

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