Head gasket question

[X-Runner]

Two cylinder stroke engine with o-ring style head gasket and another o-ring for the cooling ports around the outside of the cylinders. Both dumping water into the cylinder, both gaskets also had silicone all over them and everywhere inside the cooling ports around the head. Top end was just rebuilt at a shop due to low compression. Would the silicone (was grey color) be the reason why it was leaking coolant into the cylinder? Also had 145 PSI compression on each cylinder though, one o-ring was broken but still had 145 PSI even after removing/replacing head with broken gasket. Will fire up and run once getting all water out and running with no water.

P.S. have two of these engines, both with the same issue (dumping coolant into cylinders) and both with silicone all over the o-rings.

[X-Runner]

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