This article illustrates the strong connection between slave mobility and freedom in the late 18th and early 19th century Spanish Atlantic. As historiography has clearly revealed, slavery did not always mean living under the constant supervision of masters; it entailed some autonomy in terms of physical movement and the ability to socialize, especially in urban areas. This relative mobility was crucial in explaining the rise in civil litigation brought by slaves during this period. Through the analysis of some juridical cases, the paper will show how the slaves’ notion that they could inhabit a transitional stage, getting closer to freedom as they pursued their cases or paid off their prices, drew on the practice of “conditional mobility” which allowed them to earn money or to sue.