Individuals who are held pretrial because they cannot afford to post cash bail are more likely to be convicted and their sentences are longer, compared with those charged with the same crime who are able to purchase their pretrial release. This discrepancy increases the likelihood of wrongful convictions and exacerbates mass incarceration. It degrades our so-called justice system by embodying Bryan Stevenson’s observations that “we have a system of justice that treats you better if you’re rich and guilty than if you’re poor and innocent” and that “wealth—not culpability—shapes outcomes.” While these differences in case outcomes are well-documented, as are some of the coercive factors that cause detained individuals to be more likely to accept plea deals, less is known about how and why it is more difficult to build successful cases from behind bars. Through interviews with impacted individuals, defense attorneys, law professors, and a review of available research and literature, this chapter provides information about why case outcomes are so much worse for individuals detained due to financial conditions of release, including factors that lead to coerced plea deals, the difficulty of building successful cases from behind bars, and the biasing factors that influence sentencing. This chapter then offers policy proposals that would help ameliorate wealth-based outcomes, including reforming our pretrial system to adopt “cite and release” practices, and to create release valves for those who do not pose a threat of flight or to a specific person, limitations on preventative detention, a right to counsel at initial hearings, and requirements for ability to pay determinations in jurisdictions that still use cash bail.