How do we know when a translation is good? This seemingly simple question has long dogged human practitioners of translation, and has arguably taken on even greater importance in today's world of fully automatic, end-to-end machine translation systems. Much of the di culty in assessing translation quality is that di erent translations of the same text may be made for di erent purposes, each of which entails a unique set of requirements and constraints. This di culty is compounded by ambiguities in the source text, which must be identi ed and then preserved or eliminated according to the needs of the translation and the (apparent) intent of the source text. In this talk, I survey the state of the art in linguistics, computational linguistics, translation, and machine translation as it relates to the notion of linguistic ambiguity in general, and intentional humorous ambiguity in particular. I describe the various constraints and requirements of di erent types of translations and provide examples of how various automatic and interactive techniques from natural language processing can be used to detect and then resolve or preserve linguistic ambiguities according to these constraints and requirements. In the vein of the "Translator's Amanuensis" proposed by Martin Kay, I outline some speci c proposals concerning how the hitherto disparate work in the aforementioned elds can be connected with a view to producing "machine-in-the-loop" computer-assisted translation (CAT) tools to assist human translators in selecting and implementing pun translation strategies in furtherance of the translation requirements. Throughout the talk, I will attempt to draw links with how this research relates to the requirements engineering community.