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Hi,

the problem here is that Mail does not offer the possibility to create Rules for outgoing messages.

As far as I know, Mail Act-On (http://www.indev.ca/MailActOn.html) adds this functionality to Mail, however I haven't tested this.

So, you'd need to install Mail Act-On and then test the following :
  • Can I create rules for outgoing messages? (Answer should be yes as this is an advertised functionality of Mail Act-On)
  • Can I define the necessary critera to identity THOSE outgoing messages I want to create a task for? (I presume you DON'T want to create a new task for ALL outgoing messages).
  • Can I fire an Applescript in the Action section? (you can for incoming messages but as mentioned above, I don't know Mail Act-On and thus have no idea as to the possibilities it offers)

If all the above is ok and you're willing to invest the 25$ for Mail Act-On then this should be possible.

Here's a link to an Applescript I wrote and use to add tasks from Mail to OmniFocus http://bit.ly/yU0yxl.
You'll however need to modify this script slightly to make it Mail Rule compatible. Feel free to ask if you need help with this last part.

Bye