Cretan Revolt
Koukoulakis was a member of a well-known Cretan family from Lakkoi, a village near Chania. Many members of his family took part in various revolutions of the 19th century as Greek War of Independence, Cretan revolt of 1866 etc. and others were officers of the Hellenic Army. Koukoulakis himself, was a volunteer during the Cretan Revolt of 1897.