Filing sent messages real-time

A new & happy iMac owner, i am organizing and just set up Mail folders. While it is easy to file incoming messages into my folders, I can't find an easy (i.e. one-click) way to file my sent messages that I want to retain in a folder. After sending, I am going to the Sent folder, highlighting a message, and copying it to a folder. At work, Outlook has a Send&File option to use when sending the original. I have read about Smart Mailboxes, but that doesn't answer to me. What am I missing? Thanks for any advice.

You’re missing nothing. This is a well-known Mail shortcoming. Mail applies rules automatically to incoming messages only. There are at least three ways to work around this limitation:
(1) Apply the rules manually every so often by selecting the messages in Sent and doing Message > Apply Rules.
(2) Go to Preferences > Composing and check Automatically [Bcc] myself, so that the rules are applied automatically to the copies received. If you do this, you may also want to set Mail to erase copies of sent messages after a certain amount of time in Preferences > Accounts > Mailbox Behaviors.
(3) Use Andreas Amann’s Mail Scripts’ Filter Sent Messages script to make Mail apply the rules automatically to your sent messages as well.

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