@Allison Mahmood Are the dates by any chance repeating events? I found that they don’t get taken into account. They still show up in my availability troubleshooting view, but I can still book slots. When I add an entry manually, it gets it and disables those slots for booking. Maybe test if that’s similar for you

Yeah, some are repeated events. But managed to fix most of it by just disconecting everything and going through it again. Guessing Apple’s API may have fucked up somewhere. Will check for issues with repeating events, cause a third of my calendar are repeating events and I need those slots to not be cross booked. Thanks for the tip