Messaging Rule on Rollover Subscription

Hello! 

We are moving into subscription season and would like to support our ticketing staff by adding a messaging rule to constituents that purchased our Holiday performance last season. Specifically, we would like a messaging rule (product only) to pop up when opening rollover orders assigned to individuals on a list (constituent criteria). However, because rollover orders already have a line item for the subscription package, the message rule does not activate. It works when adding a new line item with the package, but that doesn't help with rollovers. We would like to avoid adding urgent CSIs to all of these accounts. Is there any way to do this?