In T5436#146148, @ikloecker wrote:

It's not clear whether you are talking about PIN caching related to signing operations or decryption operations.

I just wanted to chime in that I've had exactly the same experience as @lbogdan: gnupg 2.3 stopped recognizing my yubikey entirely on MacOS until the T5415 workaround (disable-ccid). After that, pin caching was broken until I applied his patch to call-scd.c:548, which makes it work as before. Without these two changes the experience with gnupg 2.3 is degraded relative to 2.2.