Reminder Notifications for Network Catchups


So I’ve been setting up a new automation to see if i can get notifications when it’s been x amount of time since I’ve had a catchup with someone. I checked out the tutorial here

It’s worked fine when I’ve done the test, my only issue is that it seems to only notify me about one record that meets the criteria, as opposed to all the ones that do. Any idea how to work around that?

Also, how long after setting up an automation will it kick in?