This Article was part of a symposium issue on Law, Labor, and Gender. This interdisciplinary project responds to legal scholars in the work/family conflict field who advocate telecommuting as a way for women to achieve workplace equality. First, the Article uses sociology research to demonstrate that telecommuting sometimes works to exacerbate gender inequality in the workplace, rather than leveling the workplace playing field. Second, the Article explores what role, if any, the law may play in requiring employers to design gender-equalizing telecommuting relationships. By analogizing telecommuting to the historic use of women industrial homeworkers, the Article concludes that targeted homeworking laws, which was the failed approach used during the New Deal Era, would face similar problems solving today's telecommuting challenges. Instead, the Article advocates the use of general antidiscrimination law.