Re-enrollment into workflows using timeline properties not working

[stephentradify]

I'm trying to get this workflow to enrol a contact any time a certain timeline event comes in. It seems to work the first time but re-enrollment does not work. Here is how I've set up the workflow:

Also I am using a test portal created by my developer account not sure if that makes any difference..

[IsaacTakushi]

Hi @stephen_c,

That setup should work... Would you share the Hub ID of the test account and links to a few contacts whom you would expect to have been re-enrolled?