What are you crimping them with?
I've had the best luck with basic dedicated crimping pliers. These are what I have:
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Though it does punch through the outer layer 50% of the time. I still tape/wrap everything anyway so I'm okay with that.
Also it looks like you're using 14-16ga connectors on 20ga-ish wire which also makes it way harder to crimp. When I'm using connectors that are way too big, I'll strip off double the length of insulation and then fold the wire back on itself so it fills the connector.