Chatbots have long been advocated for computer-assisted language learning systems to support learners with conversational practice. A particular challenge in such systems is explaining mistakes stemming from ambiguous grammatical constructs. Misplaced modifiers, for instance, do not make sentences ungrammatical, but introduce ambiguity through the misplacement of an adverb or prepositional phrase. In certain cases, the ambiguity gives rise to humor, which can serve to illustrate the mistake itself. We conducted an online experiment with 400 native English speakers to explore the use of a chatbot to harness such humor. In an interaction resembling an advanced grammar exercise, the chatbot presented participants with a phrase containing a misplaced modifier, explained the ambiguity in the phrase, acknowledged (or ignored) the humor that the ambiguity gave rise to, and suggested a correction. Participants then completed a questionnaire, rating the chatbot with respect to ten traits. A quantitative analysis showed a significant increase in how participants rated the chatbot’s personality, humor, and friendliness when it acknowledged the humor arising from the misplaced modifier. This effect was observed whether the acknowledgment was conveyed using verbal, nonverbal (emoji), or mixed cues.