This article explores intelligibility between the Jamaican vernacular, an English-based lexicon Creole language, and English. It examines discourse in pre-trial interviews conducted by functionaries in the UK criminal justice system, usually police and customs officers and lawyers, with Jamaican Creole (JC)-dominant or monolingual speakers who are typically persons suspected or accused of offences or potential witnesses of offences. Using discourse analysis techniques, it highlights instances of miscommunication and lack of comprehension not only between the parties to the interview, but also on the part of the transcribers. The analysis attempts to trace the miscommunication and lack of understanding to linguistic distinctions between the two language varieties. The paper also explores the possible legal consequences of these language-related miscommunications or lack of communication. The analysis underscores the need for continuous interpretation during pre-trial interviews and for interpretation/translation services at the transcription stage despite some similarity between the two languages.