Students with intellectual and developmental disabilities need to develop many skills to interact independently in the community. This includes skills in making financial transactions, such as using an automated teller machine (ATM), paying for items with a debit or credit card, and completing transactions at a bank. When teaching such skills, generalization to the community should be a primary goal of instruction, although it can be quite a challenge. This article reviews the concepts of community-based and simulated instruction as ways to promote generalization of financial transaction skills to the community. Challenges teachers might face and the benefits of each type of instruction are addressed, and additional resources are provided, so that teachers are prepared to implement these practices with their students.