The picaresque novel has always generated widespread appeal due to the charisma and charm of its roguish main characters, who live by their wits on the margins of society. Spanish and English satires feature the perseverance and resilience of picaros who skirt and challenge the overreach of authoritarian regimes. Critics who focus on the picaresque reflect this social animus but rarely address how these authors perceive marginal societies, as not only vulnerable peoples but also environments. What were the conditions that allowed the picaresque to flourish in Scotland? Spanning from 1748-1857, this study posits that England's imaginative and physical re-engineering of Scotland prompts Scottish authors, and those of Scottish descent, to recognize not only the allyship between the picaro and local environments and climates, but also the power that stems from it. The book includes chapters on a diverse set of authors, including Tobias Smollett, Samuel Johnson, John Galt, Charlotte Lennox, Mungo Park, James Hogg, and Mary Seacole. They deploy the picaresque to foreground discrete and interconnected environments that are under duress because of English efforts to establish an imperial totality. What Van Renen calls the "Scottish picaresque" integrates the major characteristics of the genre with the picaro's response to environmental precarity. Ultimately, the texts studied here model for readers how to eschew cartographic or imperial semiotics, and recognize physical features and places long forgotten or appropriated by the state for large-scale economic development.