Windows Updates? Apple Software Updates? Windows updates I’d look for drivers, I’d do anything under the Apple Software Updater, but be sure iTunes at least is up to date. I’ve noticed different behaviors of this trust message depending on if the device was locked or not when plugged into the computer, but that was before the latest changes to the security. Guess it’s entirely possible that whatever’s needed to make it work again is in the latest beta macOS/iTunes. The latest macOS beta messed up multiple drivers for me. A Dell W15 USB-C Dock was working for me with two displays, audio, Ethernet, USB. Now only audio and Ethernet work.