Not Receiving Digital Key

No matter if it’s after 3pm or later when I’m expected to arrive, lately like the last 3 months I haven’t gotten the digital key unless I went to the desk. I have two cards on my account for incidentals. Not entirely sure what else I can do. I’ve asked Hilton and they either tell me what I already tried or they say stop at the desk but if that’s the case what’s the point of checking in on the app? Anybody had this issue and if so how was it resolved if it was?