Although the TOEFL iBT Listening test is sometimes used for other purposes, it was designed primarily for use as a college entrance examination. Item difficulty in TOEFL iBT Listening tests is the product of interactions between two sets of complex relationships: 1) relationships among numerous item characteristics themselves, and 2) relationships between item characteristics and an extremely diverse international test taker population. In this article, Alan Shaw shares his thoughts on the art of crafting item difficulty in TOEFL iBT Listening tests. His perspective incorporates elements of the training he received at Educational Testing Service (ETS), and it also draws upon his years of experience collaborating with ETS colleagues and studying item performance statistics.