Puns and wordplay are stylistic features that are recurrent in many literary and creative text types but are among the most challenging for humans to translate. At the same time, they have proved impervious to traditional machine translation. In this chapter, we present and evaluate PunCAT, an interactive electronic tool for the translation of puns, designed to provide specialized support to human translation workflows. Our evaluation is based on an empirical pilot study in which nine graduate students translated six English puns taken from literary works and films into German, with and without PunCAT. Combining computational-linguistic and cognitive approaches, we triangulated logging data from PunCAT and the keylogger Inputlog, verbal data from questionnaires, handwritten notes, and annotations, as well as target texts. Fine-grained analyses of the participants’ translation and decision-making processes and their interaction with the tool show that PunCAT effectively supports the translation process in terms of stimulating brainstorming and broadening the translator’s pool of solution candidates, and we have also identified a number of directions in which the tool could be adapted in the future to better suit translators’ work processes.