In this paper we discuss three key points related to error detection (ED) in learners’ English. We focus on content word ED as one of the most challenging tasks in this area, illustrating our claims on adjective–noun (AN) combinations. In particular, we (1) investigate the role of context in accurately capturing semantic anomalies and implement a system based on distributional topic coherence, which achieves state-of-the-art accuracy on a standard test set; (2) thoroughly investigate our system’s performance across individual adjective classes, concluding that a class-dependent approach is beneficial to the task; (3) discuss the data size bottleneck in this area, and highlight the challenges of automatic error generation for content words.