To back up Bob580 there, the ring compressor does not fit inside the cylinder, it merely rests on the "top of the deck".
If you're putting the ring compressor sleeve inside the cylinder, you're doing it wrong, no offense intended or implied. I use an old fashioned ratcheting-type compressor but it does take a little finesse to get it right I suppose, but if you follow the instructions to the letter and make sure the overlapping layers of the compressor are square and flush on the flat surface of the cylinder, it should be easy-peasy. Use oil on the piston and/or on the compressor but it's not so much to lubricate it for easy entry, but mainly to pre-lube the rings and the piston skirt.
You don't beat or hammer it in either -- you use a non-marring stick or rod (or butt end of a hammer like Bob580 said) and gently tap it in. When the piston "goes home" with very little effort, you'll know you did it right. If you shatter one or more piston rings on the deck because the compressor wasn't tight, you'll also know it.
