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I just quickly pug the hole with my finger and then quickly start the screw by hand.
I loose a few drops of lube but not enought to worry about.
Remember to use a good washer.
Tighten with a nice big screwdriver.
Make sure the top fill plug is tight and well sealed. It will create a vacuum that will tend to keep the lube from draining.
I prefer the hex head screws that you can position on the end of your allen wrench and minimize the time it is open--but then I'm a bit clumsy with big fingers that get in the way.
You removed the phillips head screw didn't you? Tsk. There is a reason they put a phillips head on it--so you won't take it out. The real drain screw is on the bottom of the gearcase near the nose cone end.
If you did remove the phillips screw, you can usually wiggle the shift lever intil you see the hole in the shift cradle. Now use an awl or nail to move it into position, and reinstall the phillips screw.