Hi Jason,
First i would have to ask if you could give us some more background on the scenario. What version of LANDesk Service Desk are you using? Can you send a screen capture of what you are doing and trying to accomplish?
I will give this to you though. When you have several Automatic Actions following each other, the time stamps on them act "strangely". Meaning, they do not display in the order they are processed when looking at the audit trail.
If you are going strictly by the audit trail to determine if the Automatic Action fired, then you need to make sure you have auditing enabled for each action.
Hope this helps.
Mike