Consists of 7 outgoing and 344 incoming letters, largely from 1896-1903. Chiefly concerns Bool's financial support of anarchists and their publications, especially Benjamin R. Tucker and Liberty, and Moses Harman and Lucifer, the light-bearer, distribution of literature, particularly Bool's pamphlet Liberty luminants, the philosophy and activities of anarchist friends and acquaintances, notably John W. Lloyd, as well as personal and business affairs.
The Correspondence series includes several outgoing letters from Bool, but mostly consists of incoming letters. These primarily address Bool's financial support of anarchists and their publications, especially Benjamin Tucker and Liberty, and Lillian and Moses Harman and Lucifer, The Light-Bearer. Portions of the correspondence are concerned business matters as well as with anarchist philosophy and publishing, particularly the distribution of literature such as Bool's pamphlet Liberty Luminants. Anarchist and Labadie Collection founder Jo Labadie is well-represented.
The Archival series consists of one folder containing notes, typed and handwritten, concerning Bool's donation, via Jo Labadie, of pamphlets and booklets. Also included is a short memoir written in 1932 by Agnes Inglis, the original curator of the Labadie Collection, remembering Jo and "Mama" Labadie, Judson and Margaret Grenell, and Henry Bool.