Date trigger for Workflow

I have a vCRM with a "Due Date" field. I am creating a workflow that updates a Service Status to "Late" when the due date is reached. However there seems to be a "Recur" option that is confusing me.

Does this mean that after the initial trigger, it will no longer use the "Due Date" field as the trigger to update status - and it can only be updated Monthly or Annually?

I need this to be an ongoing trigger, always looking only at the due date as a trigger. Here is the use case:

Equipment is due to be serviced by a Due Date.

Each piece of equipment has a Service Status of "Late", "In Progress", "Complete"

Once the due date approaches, the status gets changed to "Late". Once it's done being serviced the Due Date is updated to some date in the future for service. This date can change/be updated.

At any given time, the Service Status should be accurate. This will not be the case if it's triggered only monthly or annually after the first trigger.

So I am wondering if it will "re-trigger" when the updated Service Due is reached.