As many as three million households with school-aged children in the United States do not have any Internet service at home, and 18% do not have a broadband connection, creating a "homework gap" between those who can access the Internet to support their schoolwork at home, and those who cannot. Based on a series of empirical case studies of efforts to develop wireless projects across the United States, coupled with a review of relevant spectrum and wireless regulations, this study informs academics and practitioners how different wireless broadband technologies can help bridge the gap. However, as our case studies show, wireless should not be viewed as a magic bullet to solving the homework gap. Closing this gap requires social initiatives to promote uptake and productivity enhancing usage and skills levels, and financial and regulatory support from policymakers and other stakeholders.