I'm having the same issue. The check-in instructions (which do not include a photo) said "skipped" for my recent guest. It was pre-booked, so not a last minute booking. When I tried to manually send the message it would not allow me to as the scheduled time had passed. It's incredibly frustrating, as the messge has the lock code and wi-fi username and password. I ended up rewriting it in a private message to the guest before they had arrived. If I had not checked to ensure it had been sent, I wouldn't have known until the guest had arrived. Very frustrating!!!