I have to fiddle with mine a bit too.?
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These tools won't be a perfect match to the contact and will not be as good as the tool you buy from the connector manufacturer. (For several hundred dollars typically) The rear crimps on the contact sometimes needs to be pressed a little towards each other to fit in the die, and I have to bias the contact slightly towards the front. However, I can insert the contact from the back of the crimp die (At least in my crimp tool).
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Steve
WA6ZFT
hwstar