In the Windows client or web client, make a change to an entry and set some value in the "Closed Date" field.

Then in the Workflow Administration Console, open the Subscriber Trace and look for that event that you just performed. When you click on that event, the middle section should show a list of starting rules that may be applicable based on that event type. When you click on the individual starting rules, the bottom section will show the condition evaluations and whether they were true or false.

When doing this, can you first confirm that you can see your event and then confirm that the starting rules were evaluated correctly?