The dock is the cause!
I opened the back of the dock and noticed a design fault. The circuit board is apparently well secured but there is nothing supporting it underneath the board where the pins are. I’ve put a piece of rubber between the back cover and the circuit board and windows is recognising the watch every time flawlessly.
I will write on here again if the problem reoccurs but it certainly does seem the dock has a small but meaningful design flaw. This point should be made to all owners of kospet watches including if they have charging issues.
These watches are lovely and deserve to be maintained and used, it would be such a shame if people stop using them because of the docks.