I feel like I should explain why. When you load a transaction it loads the state of the workflow that it currently is in. It can't transition to another state until the record is submitted, or some other trigger occurs to push it to the next state. (Such as a button press affiliated with a transition) Now, a workflow can go through multiple states sequentially after submit or on a scheduled basis with no problem because the workflow isn't being locked into its current state by the user interface. So in order for your workflow to function as desired the conditions on the show message should be "is checkbox a and checkbox b marked" and it should be in the same state as the actions that marked them. @Jessica Bickis