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Do you guys try and squish them down into the grooves when installing them, or just let them be and hope they go in when the head and jug assembly is torqued down? These really don't want to go into the grooves.
 

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A lot of the aftermarket gasket sets have O-rings that are too thick. They should be pushed into the groove, use a credit card. DSS sells OEM O-rings. I don't know what thickness your's should be
 

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On my CB360 rebuild, I also had a set of cylinder base gaskets from CMC. When pressing them into the groove, I used the blunt end of a metal pick to press them in. It was a bit annoying because whenever I would press them down forcefully, a segment on the other side would pop up. The trick is to SLOWLY work them in a little bit at a time.
 

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The base gasket on my 450 leaked. The gasket was too thin in relation to the o-ring diameter. I pulled the engine, installed new o-rings and cut a new gasket from FelPro 1/32 gasket paper. From that experience and on, I will not use aftermarket gaskets for anything other than a pattern to cut good gaskets from quality material. I also had a leak from the cam bearing blocks. I made new gaskets from FelPro 1/64 gasket material. I use the 1/32 material for the side cases. It stands up well to maintenance removals. I made the gasket for the alternator cover and the right side cover.
 
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