MITB Cash-In?

How does MITB Cash-Ins actually work this year? It was my understanding that a prompt would show up in a match the champion is in that you could hit to do it, but I've done several matches with the champion but I still haven't seen the prompt at all. Are there certain conditions I might be missing?

I've tried doing different match types, including normal matches, I've made sure both wrestlers are heavily damaged, but so far I've got nothing. I can do the announce cash in on the title I'm trying to go for so I feel like I should be getting the prompt. Is it just more random than I originally thought?