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This study is an empirical investigation of problematic instant messaging (IM) use among university students in Singapore. It adapts Caplan's (2005) theoretical framework of problematic Internet use (PIU) to the context of problematic IM use by linking pre-existing human dispositions to cognitive-behavioral symptoms and negative outcomes of improper IM use. Four new factors—oral communication apprehension, polychronicity, perceived inconvenience of using offline communication means, and trait procrastination—were tested as predictors of problematic IM use. The results provided strong support for Caplan's theoretical framework of PIU and indicated that oral communication apprehension and perceived inconvenience of using offline means were significant predictors of problematic IM use, whereas polychronicity and trait procrastination were not. The implications of these findings are discussed.