CHALLENGE is generally perceived as a negative word synonymous with "dispute," "defy," "confrontation," and "contest." However, when resorting to dictionary definitions, CHALLENGE has unexpectedly been found to possess positive senses such as "stimulating" and "arousing competitive interest," "thought," or "action." This study aimed to investigate how CHALLENGE, identified as having pleasant senses yet often categorized with negative words, interacts with neighboring words to achieve particular meanings. The semantic prosody of CHALLENGE as a verb and a noun in four grammatical relations was investigated by analyzing data from ukWaC, a web-based corpus containing approximately 1.5 million words. Two target units were analyzed: collocates with CHALLENGE and broad units (longer sequences) with CHALLENGE. The results showed that, in addition to the unpleasant prosody describing the intensity of difficulty or causing and meeting trouble (e.g., "pose a huge challenge," "face a tremendous challenge"), CHALLENGE expressed positive prosody (e.g., "set a simple 'challenge'," "ready to meet a 'challenge'," "bring an exciting 'challenge'"). Moreover, evidence was uncovered indicating that the semantic prosody of a particular syntactic structure in broad units is distinctive. For example, [CHALLENGE N.] had a more favorable prosody, such as "needing or desiring to challenge unfair/unreasonable ideas", while [ADJ. CHALLENGE] tended to occur in an unpleasant environment that suggested "causing or suffering from an extremely undesirable situation." In summary, the present study showed that although CHALLENGE was found in the same category of words possessing negative senses, its prosody could be positive. These findings have renewed our understanding of CHALLENGE, illustrating how CHALLENGE acquires positive or negative associations through its collocational environment. Pedagogic-wise, the findings herein can serve as a base for language instructors to design teaching materials and to help EFL/ESL learners avoid making overgeneralizations in their use of semantic prosody