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I changed the gear lube in my Mercury 90 HP gearcase on my Montauk 170 last fall. After draining it I filled it back up to the two vent plugs, screwed them in and then pulled out the pump and put in the drain plug.
I really had to crank down the 3 screws to stop it from leaking. I think one still leaked a little. As luck would have it a Mercury mechanic was passing by in the boat yard and told me you have to replace the 3 screws and washers when changing the lube in the gearcase. It's a new boat and I went to a Mercury dealer to get the pump and lube and they didn't say a thing about new screws or washers. The manual does not either. Anyone with info would help. Can't see the boat now to see if it's leaking because it is locked up in storage.
The gearcase drain and vent plugs do not need to be replaced every time they are removed but the Fiber washers should be.
No not use the old plastic washers, use only the blue fiber washers.
Be sure you remove the old washers before installing new ones. Sometimes they stick in the gearcase and with a little oil on them, they can be very hard to see. I use a very fine Dentists's pick to VERY CAREFULLY remove the washer if it is stuck in there.