Troubleshooting Workflow Issues: Finding the Disconnect in Requirements

Hi all, I am having a bit of trouble with my workflow. It is supposedly running and all, but I made sure that the test email its going through ticks all the boxes on the requirements for another action, but for some reason it is saying that it doesnt meet the requirements. Is there a way I can identify where the disconnect is happening? Some kind of "prompt debugger" or something?