Semi-automated rule based data annotation is a frequent pattern that emerges in all kinds of user interfaces. The example that is probably the most wide-spread is email filtering, where a user sorts incoming email into different folders on their system. Typically this is a process that necessarily contains manual decisions done by the user on a case by case basis, while also some email can be categorised automatically by applying rules. For the user to be able to define helpful filtering rules, the interface needs to be expressive enough to allow for different use-cases, while being restricted enough to not result in filtering rules that are impossible to apply.

In this thesis I investigate this data annotation workflow and how the user interface for designing the filtering rules can be built. My software implementation is able to sort bookkeeping transactions into different account names, as it is a typical workflow for the bookkeeping department in small associations and corporations.