The purpose of this study was to explore the multidimensional roles of disclaimers in Thai communication, emphasizing the factors influencing the perceptions and therefore the interpretations of the messages conveyed. Through a mixed-methods approach, this two-pronged study encompassing a survey and semi-structured interviews attempted to analyze the perceptions of the hearer and overhearer towards disclaimers. The findings indicated that disclaimers are capable of paradoxically strengthening the speaker's intent and therefore bolstering negative implications for the listener. This is in stark contrast to the often-taken-for-granted function of disclaimers as simply a mitigating device. In other words, the participants realized that disclaimers accompanying face-threatening acts could render their effectiveness dubious. That is, the listener may find the use of disclaimers as an insincere or uncertain attempt rather than a means to assuage discomfort. Further, contextual factors come into play when it comes to the interpretation of a given disclaimer, e.g., tone of voice, familiarity with the conversation partner, and social dynamics. Disclaimers in Thai are truly context-dependent, thus defying the simplistic view of linguistic politeness. Equally important, the findings reported suggest that there exists an important interplay between metapragmatic awareness and social dynamics, thereby emphasizing the importance of the motivations and implications underpinning given instances of disclaimer use.