Hi @RBirchall,
This is unfortunately a bit more complicated than it should be, as HubSpot stores only the latest value in a property. The approach here would require an additional custom date property, see this workflow draft:
I haven’t tested this so there’s a chance this doesn’t work as expected:
Re-enrollment makes sure this workflow is triggered for every new session
If/then branch checks whether last session is more than 30 days ago
If yes, the notification will be sent
In any case, the new session will be logged to the date property, effectively resetting the 30 day counter
@webdew, your workflow would send a notification regardless of whether there has been a new session or not.
Hope this helps, @RBirchall!