Archives of historical and cultural data, such as the UK’s National Archives, receive huge volumes of enquiries from users. These have been seldom systematically studied, despite the obvious benefits to the organisations concerned and interaction designers. The literature looking at the spectrum of remote communications carried out by a modern archive is sparse. Similarly, there is a lack of information about the problems users are having with archival information systems, and no information on the distribution of problems or where in users’ information seeking journeys they occur. This paper reports on a mixed-method study using content analysis and grounded theory to address these gaps in the literature. The results of the study indicate that users primarily are encountering problems knowing where to start looking or where to look next in their information seeking journeys. Further, these problems seem to create a deep anxiety or uncertainty in archive users which drives them to seek reassurance and guidance from human archivists, who will provide the type of disambiguation and support that current information systems do not. The paper closes with implications of this work on the future prioritisation of design practice and research in online archives.