There's been a few issues regarding the hitbox for that, but the primary one is that there isn't a proper tell for when it's time to clock out. That's when milking is turned off, and you have to go clock out for the night to start the next day. (That also means making sure you clock in the next day too; and do not enter the area without clocking in first) We'll find better ways to telegraph these things when we get back to developing it; right now Mutasheep is working on other projects and I'm busy with work (and was busy with holidays) so sit tight and for now just manage your time in game properly ;p