Financial responsibility is an important step toward independence for any student. This is particularly true for students with Intellectual and Developmental Disabilities (IDD), who may not have access to instruction in personal finance or basic financial transactions. When planning for transition, teachers should take into account skills students need to develop good personal finance habits, including planning high-quality instruction in financial transactions. Engaging in financial transactions involves knowing how to access and spend money. The real test of instruction in community-living skills, such as financial transactions, is whether students can use these skills in the community setting. There are several strategies that researchers have identified to promote generalization; however, historically there has been some debate over whether instruction in community living skills should be taught using community-based instruction (CBI; i.e., instruction delivered in the natural setting using materials found there) or simulated instruction, where teachers provide instruction in the classroom by using methods that approximate the natural environment. Proponents of CBI argue that instruction in the community leads to better generalization outcomes than simulated instruction; proponents of simulated instruction argue that it is more appropriate given the logistical challenges and unpredictability of providing CBI. This article argues that a combination of the two can support the generalization of skills while mitigating some of the challenges.