Automations won’t work on records that met the trigger criteria before the automation was turned on. If you want to have that automation run on those records, you need to re-trigger them by removing and then resetting the conditions. (You might try simply checking and then unchecking the box to see if that works; otherwise you need to change both conditions.)
You can also run live tests in the Automations panel by using the button to the right of the Run History. I think it’s called Test Automation? It doesn’t generate a preview, it actually runs the automation as written.