Scholarship on Matt 5.25–6 has focused on the question of whether the saying offers mundane wisdom or threatens divine judgement, with the majority concluding that it refers to eternal punishment in hell. This article examines debt-prison and related phenomena before turning to the illuminating history of ancient interpretation. The article concludes that the ‘eternal damnation’ gloss widely favoured today is an overinterpretation first inspired by the exigencies of fourth- and fifth-century doctrinal controversy. Instead of eternal perdition, Matt 5.25–6 and its parallels suggest a time of straits followed by possible release.