Current second language (L2) listening research has lacked detailed accounts of L2 listeners' difficulties comprehending texts comprising orthographically known lexis. In the current study, 15 first language (L1) Japanese English language learners of three English proficiency levels listened to sentences and a narrative text. A two-task diagnostic procedure using L1 recalls and L2 repetitions was employed to understand how orthographically known lexis was often misinterpreted over the course of multiple listening opportunities. Evidence from transcripts showed that the factors likely causing listening comprehension difficulty were L1 phonological influence, English connected speech modifications, and misinterpretation of top-down contextual information. The study results show that even texts comprising high-frequency vocabulary or other orthographically known lexis can be persistently difficult for L2 listeners to comprehend. The results thus challenge some current assumptions in L2 listening literature about the comprehensibility of texts with high-frequency vocabulary or orthographically known lexis.