The letters of former ragged school children are the basis of this chapter. In analysing the letters Ware received, this chapter draws attention to the continuity evident. It argues that the assistance Ware offered correspondents was strikingly similar to that he had previously. Letter-writing enabled relationships not only to endure, but to develop. In examining the salutations and valedictions used together with the content of the letters, it draws attention to the dynamic and changing nature of the relationships. Ware was a source of stability to some former scholars, representing an ongoing connection to both their homeland and pasts. This chapter underscores the breadth of literacy skills found within ragged school classrooms, demonstrating the resourcefulness of correspondents who communicated through pictures what they were unable to articulate in writing. Finally the letters offer tangible insights into the physical and emotional hardships that young working-class emigrants experienced.