The practice of assessing student poetry is neither widespread nor widely theorised. In fact, its absence in the literature is itself worthy of comment and conjecture. This article begins with an account of a writing workshop for pre-service teachers, which highlighted the way participants found themselves tongue-tied when asked to engage in the constructive critique of others' poems. It then moves to a broad consideration of what constitutes assessment in the educational context before considering some problematics in respect of the assessment of poetry. It problematises the assessment of poetry in the classroom context by use of the trope of the figure of Truffaldino, Goldini's servant of two masters. In this case, Truffaldino is viewed as serving two discursive masters: literary criticism and high-stakes educational assessment discourse. After a selective literature review which looks at how this dual allegiance is played out in the literature of poetry assessment, it reports on a small, case study in a New Zealand school, where the drama of dual allegiance was played out with certain effects. The article concludes with some overall reflections on the issues raised.