keepers dont want to sit in the springs?

[Eagleye]

So I am using one of the hand held keeper installers, and when I push down I just cant get them to seat. Sometimes one will go in, but that's it. Any thoughts on what I could be doing wrong? I feel like an idiot, because i know this is not that hard.

 

[Eagleye]

It seems like they are compressing enough I just cant get the keepers to grab. I have them on my bench right now so maybe if I sit them down lower I can get better leverage.

If anyone comes up with anything else let me know.