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Avoid wrapped text in messages from Mail to Outlook
Authored by: jaysoffian on Nov 16, '05 05:50:24PM
Specifically, from RFC 3676, Section 4.2 (Generating Format=Flowed) Apple is going against the following recommendation:
Regardless of which technique is used, a generating agent SHOULD NOT insert a space in an unnatural location, such as into a word (a sequence of printable characters, not containing spaces, in a language/coded character set in which spaces are common). If faced with such a word which exceeds 78 characters (but less than 998 characters, the [SMTP] limit on line length), the agent SHOULD send the word as is and exceed the 78-character limit on line length.
Technically they are not violating the RFC since it says "SHOULD NOT" and not "MUST NOT" but it is highly annoying to have to use TinyURL all the time... I filed this bug under 10.2, so I'm not hopeful that they have any plans to fix it.

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Avoid wrapped text in messages from Mail to Outlook
Authored by: Roquentin on Nov 17, '05 12:01:46AM
My understanding is that the relevant part of RFC 3676 is actually paragraph 4.3, in which it is written:
[Quoted-Printable] encoding SHOULD NOT be used with Format=Flowed unless absolutely necessary (for example, non-US-ASCII (8-bit) characters over a strictly 7-bit transport such as unextended [SMTP]). In particular, a message SHOULD NOT be encoded in Quoted-Printable for the sole purpose of protecting the trailing space on flowed lines unless the body part is cryptographically signed or encrypted.
Apparently does send 8-bit characters over a 7-bit transport, so technically its behavior is correct. Not that that's any confort to those who are on the receiving end of broken URLs (not users, natch). I remember first hearing about this behavior over three years ago, so my bet is that you won't see it change in, but will eventually see other email clients improve their handling of email sent from clients observing this requirement of RFC 3676. 2 cents.

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