The contribution addresses the long-standing question of the roof covering materials for rural buildings in the Karst region and the chronology of the prevalence and replacement of straw, slates, and bent tiles from the 16th to the 19th century. The article first outlines the interpretative and chronological uncertainty of the existing literature. Next, it presents the early modern written testimonies and iconography of towns and villages in the Slovenian Littoral, demonstrating their partial discrepancy with the existing interpretations and the ambiguity of the relevant depictions. The central part of the article analyses the original archival data from real estate transactions between peasants, which contain information on the type and value of roof coverings on 27 residential and 13 outbuildings in 15 localities in the Karst region in the middle of the 18th century. Most of these houses were covered with slates, while most outbuildings were thatched, except for the Goriška-Vipava area, where bent tiles prevailed. These results provide a reliable timeline foundation for further research.