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Clean out plug - my turn, grrrr

So I did the replacement kit on both of the cleanout plugs and if you could see the smile on my face right now after ever so gently turning each of them into the lock position! I bought boat at end of 2019 and never took them out unless I had to and I can remember from early on, they were a bitch to get back in so I will be sure to take them out after each use to prevent them from expanding/contracting. The left one had the full blown ripple in the rubber skirt and the right one was starting to flare out just slightly but that is all it needs. Only remaining question is, is it necessary to spray with silicone after each use? every so often?

Thanks everyone for your input and guidance, a helpful forum is invaluable for a boat owner much less a 2nd year owner who is all thumbs mechanically. Thank you all again! I videoed putting them back in. I mean whose happy? This guy.

Funny this thread would come up... out of no where I had a heck of a time getting my plugs in this last weekend...went in fine the weekend before... I was a little pressed for time so just sprayed them liberally with silicone spray and they both went right in... I’ll be sure and inspect them tomorrow.
 
I boat in fresh water and only spray them with silicone a couple times a year.
This forum sure is a good place to hang out, isn't it.
Same here, but (on the advice of some Yamaha service techs) I coat the rubber seals in a thin layer of Vaseline...they look brand new and stay well lubricated even though I pull them out after every outing.
 
damn sure does my friend. I'll take some pics of the old ones for sure. It really is amazing how just that little bit of a misdirection in the rubber caused the plug not to go down far enough to let the notch into the groove.
 
When I took mine into a Yamaha dealer/service, a technician came out and did the same thing. Sprayed them and they went right back in. I guess that was just the calm before the storm as eventually they get too wonky.
 
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