Findings from log analyses of user interactions with the digital content of two large national cultural heritage institutions (National Museums of Scotland and National Galleries of Scotland) during the COVID-19 lockdown highlighted limited engagement compared to pre-pandemic levels. Just 8% of users returned to these sites, whilst the average time spent, and number of pages accessed, were generally low. This prompted a user study to investigate the potential mismatch between the way content was indexed by the curators and searched for by users. A controlled experiment with ten participants, involving two tasks and a selected set of digital cultural heritage content, explored: (a) how does the metadata assigned by cultural heritage organisations meet or differ from the search needs of users? and (b) how can the search strategies of users inform the search pathways employed by cultural heritage organisations? Findings reveal that collection management standards like Spectrum encourage a variety of different characteristics to be considered when developing metadata, yet much of the content is left to the interpretations of curators. Rather, user- and context-specific guidelines could be beneficial in ensuring the aspects considered most important by consumers are indexed, thereby producing more relevant search results. A user-centred approach to designing cultural heritage websites would help to improve an individual’s experience when searching for information. However, a process is needed for institutions to form a concrete understanding of who their target users are before developing features and designs to suit their specific needs and interests.