Hi @MorganW,
HubSpot won’t check these criteria daily. Enrollment triggers are only checked by HubSpot when one of the referenced properties changes and the remaining triggers still hold true. In your case, for example, when the Aged Date switches from known to unknown, but not if it simply stays unknown. If all of the values remain exactly the same between today and tomorrow, HubSpot will not re-enroll a record.
Instead of your approach, I’d recommend looking into @OliviaB’s excellent tutorial on how to create a Today’s date property. You could then use this property and the ticket Create date to calculate the ticket age via a calculation property.
Let me know if you have follow-up questions!