This paper assesses the value of high temporal frequency satellite data with various spatial sampling resolutions for multi‐scalar historic environment survey and management use cases in Scotland, specifically for broad‐brush landscape characterisation, for monitoring the condition of monuments and for the discovery of otherwise unknown sites. Dealing with a part of the world where applications of satellite imagery are almost entirely unexplored, this study takes a real‐world approach, which foregrounds the purpose at hand rather than presenting a case study from an optimal setting. The study highlights the importance of detailed imagery to support interpretation in some instances, and the challenges of obtaining time‐critical optical imagery in a part of the world that experiences significant periods of cloud cover. The real‐world availability of data in such settings is assessed, highlighting that even with daily revisits, useable imagery cannot be guaranteed. The implications of current and past tasking patterns for availability of high‐resolution data now and in the future are discussed. The study identifies the complementary roles that satellite imagery can fulfil, while identifying the limitations that remain to fuller applications of such data, in a study that will be relevant to many parts of Europe and beyond.