How could we approach mountainous rocky landscapes in the absence of detailed cadastral maps, if the 1:5.000 maps do not depict hydrography to support the understanding of soil-marks and geological erosion, if crop-marks (or “scrub-marks” of the typical Mediterranean macchia) are undistinguishable, if the over-exposure of some military photos hides shadow-features, if a road can produce a similar signature as a wall or a fault in different geological setting a few meters away, if the monumentality of some ancient constructions means that scale does not work well as a discriminating factor, \ldots? These are amongst the challenges of creating a specific protocol in archaeological photo-interpretation of mountainous rocky areas. Taking the mountainous terrain of East Crete as a demonstration case study, a simplified cadastre has been produced according to the aerial photographical evidences with the 4th coordinate as the time changes. On this generated map, the known archaeological features were placed: a data mining analysis is carried out to understand why a particular archaeological feature was visible from the ground and if and how its position influenced the recognition itself. The description of every single anomaly via abstraction levels, groups homogeneous elements in a bigger category. On the base of these first subdivisions, the comparison of similar recurrence of combination of colour/contrast allowed the description of dubious cases or the definition of “false-features”. The availability of an extensive architectural field-survey with accurate digital measurements, such as the Digital Crete Archaeological Atlas, allowed to improve the feature recognition and to address a higher number of archaeological questions. This paper discusses some results that arose from Cantoro's PhD research and their later enhancement through the further refinement of interpreta-tion. A combination of remote sensing and ground-truthing was exploited for the specific geomorphology of the area of Eastern Crete, trying to extend it even further to other geographical contexts.