Yeah, they don't just slide/drop in like you'd hope, always need a good whack to get them over the topDrax wrote: two quick hard whacks with the wood end of a hammer and she's in!

I've used the same type of ring compressor you have there. They're not ideal because it's not a consistent diameter all round (there's a small gap where the end of the inside coil finishes).
I've also used this type, which was more fiddly to use in may ways, but does a better job of compressing the rings equally;

Beauty of this type is if you use a clamp that's slightly undersize, you also still end up with a thin gap you can see through, to see exactly where abouts you are with the job of inserting (when a ring is at the top of the bore, if it actually has compressed enough, how many have gone in etc.)