This chapter discusses the open access digitisation programme undertaken by Living with Machines, exploring the range of constraints that inform digitisation strategies and selection priorities. Because the landscape of digitised newspaper collections is so complex, and research and digitisation processes operate on different timelines, we have focused on opportunities to make digitisation choices both transparent and pragmatic. Working towards solutions that reflect collaborations between library staff and scholars, we introduce: a) Press Picker, our custom visualisation tool designed to support decision making about digitisation; and b) the Environmental Scan, a process of automatic metadata generation from the Newspaper Press Directories, a contemporaneous record of British newspapers.