Entry 1 sense Webster, 1913 jailbreak · IPA /ˈd͡ʒeɪlˌbɹeɪk/ 01 n. an escape from jail; as, five prisoners escaped in a coordinated jailbreak. 1. an escape from jail; as, five prisoners escaped in a coordinated jailbreak. See: jailbreak Syn. break, breakout, gaolbreak, prisonbreak, prison-breaking.