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In all my years of using SmarterMail I had believed Content Filtering would take place on ALL messages. Unfortunately I've found out that Content Filtering only takes place on incoming messages and does not work for outgoing messages.
To my dismay I'm not able to find this documented anywhere. There's no telling how many people I've misled over the years believing that Content Filtering would work on all messages.
For example, if a Domain Administrator wanted to keep an eye on what messages a certain User was sending out I've always told them to created a Domain Content Filter with the To Address and From Address of the User, then use wildcards, and then then set the action to "Copy message" to the Domain Admin or whatever email address they desired. That way they can monitor what that user is doing.
That's just one example. I've told Domain Admins that they could block Users from sending out .zip attachments with Content Filtering. I'm just astounded to find out that after all these years I just now find out that Content Filtering is for inbound messages only.
It makes no sense at all to me.