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What am I doing wrong?

When loading on to trailer, I crank the bow winch in as much as I can. I note the bow is making contact with the rubber bow roller. But, when I pull trailer out of the water, I end up with a 1/2 to 1 inch gap between the bow roller and the bow.

I think I could manhandle the crank and pull the bow back to the roller but I feel nervous that I'm going to break something. So today I backed the boat back into the water and then was able to crank the slack out. Once again, the bow appeared to contact the roller. I pulled up out of water a second time and noted a 1/8 inch gap between roller and bow. This time I manhandled the the crank about one notch and managed to get the bow to contact the roller.

This is a 2017 170 Montauk I bought last year. Prior to that I've owned 13' Sports. Those never gave me this weird roller gap problem. I'm sure I'm doing something wrong with the Montauk. Cranking winch too much or not enough or what?