Crowdsourced transcription projects have the power to engage volunteers while vastly improving access to historical documents. This session will explore the nuts and bolts of crowdsourcing transcription through projects at the Brookline Historical Society and Historic New England. The Brookline Historical Society led local volunteers in the transcription of a Brookline woman’s mid-nineteenth-century diary, which had been acquired and digitized by Boston College. The Historical Society created an annotated online version of the diary based on these transcriptions, with supplementary information about the daily life of the author. With funding from the NHPRC, Historic New England undertook an extensive digitization project to provide online access to the papers of Brigadier General Thomas Lincoln Casey (1831-1896), renowned civil engineer, and his son the architect Edward Pearce Casey (1864-1940). Presenters Ken Liss, Lorna Condon, and Susan Jarvis will discuss challenges, present strategies, and break down the organization and management of these two successful crowdsourced transcription initiatives.