It depends on what contacts are in the connnector. One style connector is high density and has more smaller contacts in the same size connector. (Green / White insert / remove tool.)
The BACKSHELL must be removed from the connector. You will be using a Red / White or a Green / White removal tool. (SteinAir sells them.)
Assuming that you are using a Mil Spec connector that has a silicone seal where the wires go in, use a drop of IPA on the tool, thread the wire through the large opening in the metal of the connector and gently slide it into the connector. You will FEEL a click when you have relased the keepers. Now pull on the wire and it should come right out.
I have done this so many times, I can do it with my eyes closed. I hope my description helps.