This study investigated the effects of a group of task factors on advanced English as a second language learners’ actual and perceived listening performance. We examined whether the speed, linguistic complexity, and explicitness of the listening text along with characteristics of the text necessary for task completion influenced comprehension. We also explored learners’ perceptions of what textual factors cause difficulty. The 68 participants performed 18 versions of a listening task, and each task was followed by a perception questionnaire. Nine additional students engaged in stimulated recall. The listening texts were analyzed in terms of a variety of measures, utilizing automatized analytical tools. We used Rasch and regression analyses to estimate task difficulty and its relationship to the text characteristics. Six measures emerged as significant predictors of task difficulty, including indicators of (a) lexical range, density, and diversity and (b) causal content. The stimulated recall comments were more reflective of these findings than the questionnaire responses.