If you have already let QuickBooks 2009 for Mac update itself to the most current release (QuickBooks Pro for Mac 10.0.3 R4), chances are that anything in your Memorized Transactions list marked as "Automated" isn't currently triggering as it should. According to Intuit, this bug was introduced in the R4 update released last month. They are working on a fix that is "coming soon," and is "targeted to the end of this month."
If you haven't updated to R4 yet, we recommend waiting to update until R5 is released. If you have updated and need to use these transactions, you must trigger them manually. To do this, go to your Lists menu, choose Memorized Transactions, and then highlight each transaction and choose "Use" from the widget-looking menu at the bottom of the window.
UPDATE: Intuit's Ian Vacin commented below and posted a link to a workaround for this problem. By setting a "number remaining" to the memorized transactions, they should auto-enter as expected. Thanks, Ian!