With most doors this process does not go smoothly.
How to install door hinge pins.
To seat the serration into the hinge just get out your socket again and place it over the point of the pin.
This leaves the stopper assembly.
Slide the pin back into the hinge.
Taking a hammer and your nail punch gently ram the pin upwards.
Put the flat end of the nail against the pin and tap it up with the hammer.
Continue to tap it up gradually increasing the force until the pin is finally lodged upwards.
Force the pin up from the door hinge.
Line up the two hinge plates so that the ones on the door match the ones in the jamb.
Insert the hinge pin into the hole in the stopper assembly from above so that the shank of the pin extends below the assembly.
Knock the pin back into the hole using a solid base to rest on if the pin is slightly longer allow for the difference to let the bolt seat fully home.
Top hinge set of pics.
Hold the door in place using blocks under the bottom to support it if necessary.
Once the pins are out knock the brass cups out of the hinge and clean inside the bore.
The fit is tight and it will likely require some force to complete the installation.
Then install the lower pin into the top bushing moving and adjusting the door as you go to allow the pins to slide in somewhat freely.
The pins have a serration under the head and this holds the pin tightly in the hinge.
Slide the hinge pins into place and remove the blocks from the door.