The history of multi-apartment urban residences in Scotland goes back to well before Modernism and even the industrialised age, as they were frequently used in Early Modern burghs where residency was a prerequisite of citizenship, and outward urban expansion was not a viable option. This paper will investigate early examples of tenement types in Edinburgh focusing onto three main periods; firstly, the multi-storey, multi-property buildings of the Old Town in the Sixteenth century, such as Gladstone’s Land; secondly, purpose-built, speculative developments such as Mylne Court in the late Seventeenth century, also in the Old Town; and finally the adoption of an optimised, polished tenement model within Edinburgh New Town in the Eighteenth and Nineteenth century. Through a comparison of visual and written documentation, and by contextualising these buildings within their economic, social and political settings, I argue that communal vertical living in Early Modern Edinburgh can be considered an influential forerunner to the modern tenement, being faced with –and responding to- contemporary issues also faced by the modern tenement, such as the relationship between tenements and the surrounding urban fabric; the degree of separation between productive/commercial activities and spaces for inhabitation; the level of privacy to be expected within the apartment, between apartments, and in the neighbourhood; the usage of common areas such as staircases and courtyards; the interactions between different stakeholders, such as local authorities, central government, private investors, and actual inhabitants; the issue of social inclusion vs social segregation; and the requirements of serialisation and optimisation of spaces vs flexibility of use and organic growth. This paper argues that Early Modern multi-apartment, high-rise buildings offered pragmatic and flexible responses to these issues, and could represent a varied, creative, and thoughtful palette of precedents, to help frame and direct our current understanding of tenements’ contemporary role and potential.