That's not actually true. It is true that rooms are not assigned at booking. Reservations get downloaded from the central reservation system to the actual resort a few days prior to arrival date (about 5). At that point, the room assigner's at the resorts will go through all the room requests made and try and preassign rooms if needed. Connecting requests are one of the things they look for. They will attempt to honor the requests whenever possible. Now the more specific you get, it gets less likely that all requests can be honored. And, your rooms may not be ready upon arrival, even if you get there after 3pm. Rooms are usually available after 3pm (and most of the time before), however specific requests may take longer. That "connecting rooms guaranteed" shown above is a new one for me! If the two rooms are not under the same reservation, call Disney and make sure it is noted in the reservations that the two are together and request connecting. They will look for those notes when assigning rooms. And unlike a lot of hotel chains, Disney is geared to families and have a large number of connecting rooms.