In an academic environment, teachers utilize crossword puzzles to help students learn or remember terminology. Outside the classroom, typically in daily newspapers, crosswords aid in vocabulary development, used as a learning tool, a leisure activity, or both. However, both the content and the grid structure of the crosswords in these two environments differ greatly. Consequently, English language learners (ELLs) may struggle to adapt to the challenging grid as well as the U.S. culture-centric focus of a daily crossword. The purpose of this article is thus to consider as a vocabulary learning task a crossword puzzle whose content is designed specifically for ELLs, yet still abides by the grid structure of a daily crossword. Three graduate school-level ELLs worked on such a crossword; their thoughts on doing a crossword were analyzed through a written survey and discussion that was recorded and transcribed. Results reveal that participants were frustrated by the cultural components and context-less nature of the puzzle when working alone, but felt more positive and made substantial progress when working collaboratively.