From the 1610s in London, servant brokers, merchants, and eventually justices of the peace and their clerks recorded consent to transatlantic colonial indentured servitude with heightened attention. In doing so, they were responding to the vastness of the distances servants crossed, compounded with the multi-year length of their contractual terms and the unlikeliness of the servants returning home. The assignability of these contracts further differentiated them from the contemporaneous forms of indentured labor. In this newer system, contracts more often specified the voluntary nature of servants’ agreement with a free will clause, precisely because their willingness seemed implausible. The treatment of different categories of recruits, including adults, children, convicts, and paupers, are compared. Unwilling recruits could sometimes secure their release before the ships departed England. Sealed indentures made escape far less achievable.