This paper examines the attempts of freedpeople—before and after they voyaged to Liberia—to secure the freedom of family members, and in particular, spouses. Through petitions and campaigns to enslavers as well as the Colonization Society, subscriptions and fundraisers to attempt to purchase the freedom of kin, and letters sent from Liberia to the U.S., newly freed people attempted to reconstitute their families in this incomplete freedom, but were not always successful in doing so. In a cruel twist, one of the central freedoms that Liberia did claim to offer to settlers (and require of them) was legal marriage, which remained unavailable to already-separated spouses divided by legal status and the Atlantic. Using records from the Colonization Society, manuscript letters written by settlers, and documents from the Liberian legislature, the paper argues that Liberian colonization forced painful separations in order for settlers to obtain freedom.