it's the SMTP client who's job it is to double up dots that start on a new line. In your sendmail command case, that would be the sendmail command, so that's where the problem would be. I think you agree with me on that. Your SMTP server does seem to do the right thing though, so it's just the sendmail command and how it interacts with your SMTP server.
I don't know if I'm willing to make a hack in Dada Mail to get around broken sendmail commands, as it doesn't seem to be universal. In fact, it may just be you having the problems - you may want to see if you can find more info on the type/version of your sendmail command - a simple,
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Lots of reasons why I don't wanna handle this myself: the CPAN module that handles quoted-printable encoding is very very mature, and I don't think there's a bug in it (or at least this bug). There's also no way to tell it what characters to encode, so there's no way for me to tell it to encode dots. I don't ever directly interface with this module either - I interface with the MIME Entity module, which is also very mature, but does not have any options to handle dots that start a line.
For you, perhaps switch your encoding? Base64 would hide those dots for ya,