"win this game of Dota to dismiss the modal"

gonna call this "Tyler Mode"

Thinking specific companies like Tally and Linear

There is also the hidden variable of if the customer has sorted you into the "provides updates" category. There are companies who send a weekly digest to everyone, they've been doing this for years and customers come to expect it, so when it's actual big "new feature" time people are primed.

Could not agree more. The worst part is when someone cancels for a missing feature... that you actually have.

I'm sort of working on this problem and I don't think theres a silver bullet, but instead takes a lot of different approaches for different types of customers.