You already figured out how to get it going.
You need 2 people.
Remove the headlight and side marker. Then you can see what is going on.
First person sticks a long tool, like a big long screwdriver, through the sidemarker hole. First person pushes against the back of the female plug with a tool so it does not move while you slide in the headlight.
Second person slides in the headlight while the female plug is is prevented from moving away by the first person pushing in the headlight.
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