Face masks affect the transmission of speech and obscure facial cues. Here, we examine how this reduction in acoustic and facial information affects a listener's understanding of speech prosody. English sentence pairs that differed in their intonational (statement/question) and emotional (happy/sad) prosody were created. These pairs were recorded by a masked and unmasked speaker and manipulated to contain audio or not. This resulted in a continuum from typical unmasked speech with audio (easiest) to masked speech without audio (hardest). English listeners (N = 129) were tested on their discrimination of these statement/question and happy/sad pairs. We also collected six individual difference measures previously reported to affect various linguistic processes: Autism Spectrum Quotient, musical background, phonological short-term memory (digit span, 2-back), and congruence task (flanker, Simon) behavior. The results indicated that masked statement/question and happy/sad prosodies were harder to discriminate than unmasked prosodies. Masks can therefore make it more difficult to understand a speaker's intended intonation or emotion. Importantly, listeners differed considerably in their ability to understand prosody. When wearing a mask, speakers should try to speak clearer and louder, if possible, and make intentions and emotions explicit to the listener.