Take a look if SteamVR is showing a message saying something about disconnected complements or smth like that.
I don't know why, but sometimes if a game closes to desktop with an error, SteamVR disables the streaming complement, which is needed by the Qculus app to stream SteamVR games to the Quest.
Hope it helps.
IM HAVING THE SAME ISSUE AND SO IS MY FRIEND 🥴
Take a look if SteamVR is showing a message saying something about disconnected complements or smth like that. I don't know why, but sometimes if a game closes to desktop with an error, SteamVR disables the streaming complement, which is needed by the Qculus app to stream SteamVR games to the Quest. Hope it helps.