The project ‘First-Hand Accounts of War’ is concerned with the digitization and so-called ‘datafication’ of more than 190.000 pages of historical – mostly – handwritten letters. With a digital poster presentation at the DH Benelux 2021 conference, the project members are reaching out to other institutions, projects, and researchers for inspiration, discussion, and collaboration. The archival collection, the first steps in the digitization process, and the particularities and difficulties encountered along the way are presented. The poster aims to contribute to current debates on the impact of decisions in the digitization, transcribing, and annotation phases and anticipate research applications and possibilities in the future.