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Woodland, sorry if this sounds elementary, buy how old is your socket? Would it help if you invested in a new six point socket? It might provide a better grip and be less likely to pop off. A few bucks for a new tool might save time and further problems.
My oil stainer plugs took a solid push using a breaker bar and an extension. I probably used my 1/2 inch breaker bar, which is a lot easier to hold steady even if you don't need that much additional torque.
Obviously you want to apply force squarely and avoid further "pop offs," since you may be rounding the corners off the fitting. Good luck!
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