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Incompatibility in Protocol: E-mail sent from Thunderbird sometimes doesn’t arrive at Hotmail

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In my post about incompatibility below, I wasn’t that surprised that some things just don’t work under Linux. But with Windows XP now installed again and with Mozilla Thunderbird for my e-mail, I really didn’t expect anything to be incompatible.

Untill I tried to send an e-mail from my student account (in Thunderbird) to my Hotmail.com account. It just didn’t arrive, again and again. This makes you think: Mail is supposed to arrive at the receiver computer, right? But there is also a business in that doubt, just think about the response message for succesfull deliveries. Did they get it? In this case, I was doubting if the mail I sent to Hotmail adresses over the past month actually even arrived.

So I started searching the web to find some answers, because I thought a small setting in Thunderbird was going to solve the issue. But it turned out to be something that wasn’t solvable with just the click of a mouse.

Check out this post by Daifne from the MozillaZine forums:

Problem:
Intermittently, can’t send messages to hotmail.

Solution:
Insert HTML formatting in message and vary message contents.

Factors:
It looks like a Baysian e-mail filter between Bell Sympatico and Hotmail is being used to automatically delete e-mail messages. They DO NOT show up inthe Junk E-mail folder on the hotmail account.

Baysian filters use a technology that weights a number of factors to
determine if a message will be sent. +1 represents likelyhood of
uccess. -1 represents likelyhood of failure. If you score low on too many categories, the e-mail will be deleted.

The discussion this post sparked on the MozillaZine forums of course took the form of an angry mob trying to burn down Bill Gates’s house: “This is only an issue when sending to Hotmail accounts and that is exactly what Microsoft is trying to get you to do here. Are you going to fall for their fraudulent business practices?” But where does the cause of incompatibility lie? With the sender or the receiver, or perhaps the signal itself? The willingness to make compatibility possible? Microsoft’s alleged monopoly position doesn’t speak for the company. But the ideal of free software on the other hand also forces expectations that can not be met on companies that employ thousands of people.

But back to the solution for my problem? The first sounds a bit strange, if the content of your message is varried enough it does get through. But if you just want to test your account with a small messsage, chances are big that it doesn’t come through.

Luckily I have a Hotmail/Windows Live account in Thunderbird and use the localhost/Hotmail SMTP account that is created by the Webmail extension to send all my email through. It works, but it is a work-around and not a shining example of compatibility. With thanks to this post from Ambiguity on the DI Forums Board. More info also on this page by Ian Gregory called The Black Hole Called Hotmail. Pictures from Wikipedia.

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