A stripper head assembly for holding back pressure while stripping a work-string in and out of a pressurized well environment. The stripper head assembly comprises a stripper head, a stripper insert, a stripper rubber, one or more retention bushing assemblies, one or more retention pins, and one or more retention apertures. The stripper head comprises an outer portion of the stripper head assembly. The stripper head comprises, from top to bottom, a top portion, a body portion, a lower neck portion and a flange base. A portion of the stripper insert fits within a portion of the stripper rubber. A portion of the stripper rubber fits within a portion of the stripper head. A portion of the stripper insert is configured to fit within a portion of the stripper rubber.