HIC connector assembly

Anyone have any tips on inserting the small gauge wires and pins in the HIC connectors?  The 14 and 18 gauge wires went in fairly easily for the fuel pump and lane power pins, but the 22 gauge wires have been nearly impossible.  I got a couple to go in but most won’t go and the small wire just collapses during the attempts.

I tried to use a milspec pin insertion tool and that caused one of the pins to come out through the hole for the needle nose pliers and is now jammed in and won’t budge.  I will need to buy another MX150L housing and try again, but I’m leaning towards ditching the abominable Molex connectors entirely and cutting off the factory connectors and replacing with Deutsch or milspec circular connectors that are easily to use.

Is there a trick to getting the small gauge wires and pins to go into these connector housings?  And, yes, I did ensure that the while locking plate was pulled out before inserting the pins.