This study used a multiple probe design across participants to examine the effects of classroom simulation using static picture prompts to teach students to make a purchase using a debit card and track expenses by subtracting purchase amounts and adding deposits into a check register. Results demonstrated a functional relation between simulated instruction and students' ability to complete a 20-step task analysis of debit card use and expense and deposit tracking in a check register. Students were also able to generalize the skills of purchasing with a debit card and tracking expenses and deposits in community settings up to five weeks post-intervention. Implications for practice and recommendations for future research are described.