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Hey Kimberly, I'm working on a similar flow and what I did was pull down all records from my custom object, and all records from my standard object. The match was the User ID in my case, but yours would be the ContactID. Your decision would be, If Course Object Contact ID matches Contact ID then do (insert desired action). Its a fairly complex flow since you have a few scenarios to account for but I would suggest doing a flow diagram of some sort, either with a program or a white board, but that should help you identify all your possible scenarios. Good luck on your design, it's taken me about 2 months to get mine to almost perfection. If you're looking for some guidance on where to start there are some good things in Trailhead and also Automation Hero. Oh and if you want to send a custom notification be sure you get the Notification ID from Dev Console, thats the only place you can grab it.