The Housing Choice Voucher Program struggles to assist families in accessing low‐poverty neighborhoods. This paper explores a newly introduced incentive in the voucher program in Milwaukee County that could expand its potential to improve locational outcomes by providing security deposit assistance to households who move to a suburban jurisdiction. Using in‐depth interviews we examine the different ways voucher users responded to the program and how it interacted with their life experiences and search strategies. Our interviews highlight the role of housing instability and discrimination, as well as the role of informal search assistance and the appeals voucher users make to persuade landlords to rent to them. Our study speaks to the limits of “nudge”‐like policy incentives and emphasizes how choices about moving are influenced not only by incentives but also by a stratified housing market. We conclude with policy suggestions based on our findings that could make suburban searches more promising for voucher holders.