The itinerant poor were forced to improve their situation by appealing to various communities. Wherever they arrived, they would approach the synagogue or teacher’s room, and community members made an effort to care for them. In this article, I present charity letters from different communities in Yemen that the itinerant poor took with them, and I discuss the structure of the letters and their content as well as issues of formulation and language reflected by the letters. A study of the charity letters shows that the writer used rhetorical means to convince the readers and listeners to contribute to the person presenting the letter. At the beginning of the letter, the writer uses famous figures known for offering charity as well as biblical verses and rabbinic sayings about giving charity. In the ensuing comes the life story of the petitioner for charity, and at the end of the letter, the writer specifies the reward for the giver of charity, which is another means of persuasion.