To do my work properly I am dependent of collegues, suppliers and clients that actually answers my mails, and do what I order them to do. To control this, I have various help from other applications, as well as a "Monitor" mailbox in Mail.app. I imagine that a lot of people have the same "problem" - ie people don't always do what you want them to do... Therefore I am looking for a mail application that do something like this: 1. I send a mail. 2. The moment the mail leaves it also enters a "monitor queue". 3. After N days (2 perhaps as default) a dialogue or something pops up that asks if this has been solved, with some options on what to do (Demand answer, This has been solved, Defer, Resend etc etc) Details: - If an answer to the original mail enters during the monitor time it will automatically leave the queue. - You should of course be able to remove and add things to the queue manually. I have experimented with the rules section in Mail.app, but it seems that rules are not triggered by outgoing mail. Any ideas for how to create this workflow?