Introduction: Medical students are expected to develop competencies in applying clinical knowledge. Progress testing is an assessment for learning and is intended to assist in knowledge acquisition and to promote ongoing recall. This study explored student preparation for progress tests (PTs), relationships between approach and performance, and patterns that could assist with targeting learning support. Methods: A cross-sectional survey exploring study approach and learning context, comprising multi-choice and open-ended responses, was administered to students during their clinical years (n = 297). Quantitative data was analysed using descriptive statistics and comparative analysis, and qualitative data was categorised. Results: One hundred twenty-nine students responded (43.4%), with most demonstrating a stable PT performance over time. Twenty-two students had dynamic changes in their aggregate grades. Poor early PT performance was associated with developing an improvement strategy (χ2 6.954, p = 0.008). Students never falling below satisfactory were less likely to have a strategy (χ2 10.084, p = 0.001). All poorly performing students were using practice question banks, but this was not true for students who scored satisfactorily. The need for pastoral care was associated with poorer performance (χ2 4.701, p = 0.030). Conclusions: Student approaches to PT preparation are diverse, however there are correlations between preparation factors and performance outcomes. Students with poor early performance demonstrated improved results over time that may be attributed to targeted support and preparation strategies. Widespread use of practice questions may not be sufficient to impact results without additional strategies. External impacts to performance were common, and barriers to accessing pastoral care were evident. The feedback dashboard was underutilised, suggesting a need to improve feedback literacy and ensure this is fit for purpose.