Forensic science is currently undergoing a transformation and expansion to include modern types of evidence, such as evidence generated by digital investigations. This development is said to raise a series of challenges, both in operational and conceptual dimensions. This paper reviews and discusses a series of convoluted conceptual hurdles that are encountered in connection with the use of digital evidence as part of evidence and proof processes at trial, in contradistinction to investigative uses of such types of evidence. As a recent example raising such hurdles, we analyse and discuss assertions and proposals made in the article “Digital Evidence Certainty Descriptors (DECDs)” by Graeme Horsman (32 Forensic Science International: Digital Investigation (2020) 200896).