This study addresses a controversial issue in the adiabatic piston problem, namely that of the piston being adiabatic when it is fixed but no longer so when it can move freely. It is shown that this apparent contradiction arises from the usual definition of adiabatic condition. The issue is addressed here by requiring the adiabatic condition to be compatible with the invariance of total entropy under a system–surroundings interchange. This paper also strengthens some recently published ideas concerning the concepts of heat and dissipative work, and is primarily intended for teachers and graduate students, as well as for all who are interested in this fascinating problem.