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Rates of Supplemental Security Income (SSI) recipients who attempt or return to work remain persistently low despite demonstration projects aimed at addressing work-related barriers and qualitative and survey research suggesting that SSI recipients often have the desire to work. To better understand the factors that SSI recipients themselves perceive as most pertinent to their capacity to work, we used a community-engaged research approach to qualitative methods across two research sites in California and the mid-Atlantic. Thirty-seven in-depth, semi-structured interviews with working-age adult SSI recipients were conducted across the two sites followed by two member-check groups. Both inductive and deductive approaches to qualitative data analysis were used to code interview transcripts. Participants offered concrete recommendations for SSI policy and policy administration that they felt could improve their experiences and even facilitate opportunities for work. These recommendations often did not focus on work incentive programs, instead they were situated outside of policy silos and in the interactions between SSI policy and the context in which they lived. Recommendations include increasing program flexibility to reflect the reality of fluctuating disability; introducing SSI navigators to help understand complex rules and troubleshoot barriers such as bureaucratic errors along the way; and increased use of online systems for communications with the Social Security Administration.