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Digital technologies allow unprecedented preservation and sharing of world-wide cultural heritage. Public and private players are increasingly entering the scene with mass digitisation projects that will make this possible. In Europe, legislative action has been taken to allow cultural institutions to include in their online collections copyright works whose owners are either unknown or non-locatable (“orphan works”). However, according to the Orphan Works Directive, cultural institutions must attempt to locate the owner of a work before using it. This is the so-called “diligent search” requirement. This paper provides an empirical analysis of the conditions under which a diligent search can feasibly be carried out. The United Kingdom, the Netherlands, and Italy, all of which have implemented the Orphan Works Directive, have been selected as case studies. For each jurisdiction, this analysis determines what the requirements for a diligent search to locate copyright holders are, what the authoritative sources and databases to be consulted are in practice and, most importantly, to what extent these are freely accessible online. In doing so, our analysis provides insights into the two main issues affecting cultural heritage institutions: (1) how much legal certainty does the implementation provide, and (2) what is the practical burden of a diligent search. The analysis reveals that the jurisdictions have given different meanings to the term “diligent”. While the UK’s extensive guidance makes it unlikely that a search would not be deemed diligent, the search burden is onerous. On the other hand, Italy and especially the Netherlands have a lighter search burden, but in the absence of clear, definite guidance, the likelihood of accidental infringement by failing to meet the diligence standard is greater. In addition, all three jurisdictions have so far failed to take the accessibility of the sources into account, making the searches even more onerous than the numbers suggest at first sight. Therefore, it will be difficult for cultural institutions to clear the rights for their collections while fully complying with the requirements of the legislation. This article concludes that legislative action, official guidelines, or jurisprudence are needed to establish a different legal value of sources for a diligent search, with various degrees of optionality depending on data relevance and accessibility.