At a time when language trainers need to determine how best to integrate new digital tools that provide students with linguistic information, our aim in this article is to assess the potential value of information provided by two types of tools now widely used by students: machine translation via online translators and state-of-the-art generative AI platforms such as ChatGPT. In particular, the aim is to explore whether access to such information can help students develop their linguistic analysis skills to improve their understanding of the language prior to performing a translation task. Our case study deals with the analysis of complex English compounds—a known challenge for French learners of English as a second language—and involves two distinct cohorts: students in their third and final year of an undergraduate program in applied foreign languages, and students in their second and final year of a master’s program in professional translation. We evaluated the participants’ ability to identify head nouns—a necessary skill for comprehending complex noun phrases—under two conditions: (i) without access to any additional information and (ii) with access to machine translation outputs provided by a generic online translator. Subsequently, we explored the capabilities of advanced generative AI tools—in this instance ChatGPT—in correctly identifying head nouns. Our results show that students may benefit from the presence of machine translation outputs, albeit with varying degrees of success. However, our experimentation with ChatGPT suggests that generative AI tools may be more effective in helping students analyze and understand complex noun phrases in English, in particular since the launch of ChatGPT-4o.