"Rules" not functioning for organization of Mail.  Please advise.

In order to make my life easier, I've set up some rules to help organize my mail. For example, I set up a rule that says:
If the From contains [email protected]
If the To contains [email protected]
Move message to the folder entitled myfriend.
This rule works for all incoming mail, but does not work for sent mail. Why not? And what do I need to do so that all email, either recieved from that person or sent to that person always ends up in the same folder (i.e. the "myfriend" folder which is located in my Imports folder, meaning it is taken off the mail server)?
Please advise
Best,
Tim
Powerbook G4 Aluminum   Mac OS X (10.4.4)  

Landolphe,
First of all the update from 10.4.3 to 10.4.4 did not do any updates to Mail, so that should not be an issue. Your short description of the Mailboxes folder does not immediately seem out of line, but difficult to tell, yet.
If anything has taken place to move any folders and mailboxes around, then Rules can sometimes lose track of the target mailbox -- have you moved anything, either in the Sidebar of the Mail window, or using the Finder?
If your mailboxes, or at least some of them, originated in Panther, I want you to read the article at the link below, and then get back to me with some observations, before attempting any changes:
http://docs.info.apple.com/article.html?artnum=301315
This issue of leftover files applies not only to mailboxes you have previously created (which are in the Mailboxes folder the article mentioned) but can also apply to those mailboxes in account folders created prior to the upgrade to Tiger.
Also, please report the size of each file or folder. Do not, however, try to list the files that are within the folder named Messages, that is found in each and every mailbox.
More info, please.

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