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jr and I were recently talking about how to make Microsoft Outbreak1 send UTF-8 emails using the quoted-printable content transfer encoding2. It seems that by default, Outbreak sends UTF-8 messages in Base64. Not only is it a waste of bandwidth — a quick test showed that an average UTF-8 message in French weights a third more in Base64 than in quoted-printable — but it is also problematic because some spam filters, especially those filtering mailing list posts, tend to give a high junk rating to Base64 messages on the grounds that an encoded attachment is probably a virus. Likewise, the recently released SpamSieve 2.0 can be configured to systematically flag Base64 HTML messages as spam.

Unsurprisingly, there is no setting in Outbreak to make it send quoted-printable UTF-8. This is because the problem is in the Exchange server. In Exchange mode, Outbreak sends messages using the MAPI3 interface, which leaves the burden of encoding to the server. And the server makes Base64. The million dollar question is therefore: how do you make Microsoft Exchange send UTF-8 emails using the quoted-printable content transfer encoding?

The short answer is: you can’t. The long answer is: it is not possible.

But if there’s only one thing we remember from the Mathematics courses we followed during our studies, it is this: when you don’t know how to solve a problem, try and reduce it to a previously solved form. In our case, to prevent the spam filters from rejecting our emails, we only need to prevent Exchange from sending them in Base64. And this is easy, provided we are properly equipped:

First shalt thou take out the Holy Pin. Then, shalt thou count to three. No more. No less. Three shall be the number thou shalt count, and the number of the counting shall be three. Four shalt thou not count, nor either count thou two, excepting that thou then proceedest to three. Five is right out. Once the number three, being the third number, be reached, then, lobbest thou thy Holy Hand Grenade of Antioch towards thy Exchange server, who, being naughty in My sight, shall snuff it.
— Armaments 2:18-21

1. Daring Fireball: Good Times by John Gruber 

2. The reason for sending UTF-8 messages should be obvious but will be discussed in an upcoming entry. 

3. Mamma mia, Another Proprietary Insanity. 


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