Evidence from production studies demonstrate that /s/-retraction, a sound change in American English where /s/ approaches [ʃ], is progressing in apparent time and highly context-dependent, occurring overwhelmingly in /str/ clusters. This study reports findings from a phoneme categorization task, suggesting that listeners perceive sibilants in /str/ clusters less categorically than in /spr/ and /skr/ clusters and are becoming less categorical in apparent time for all clusters. Indicators of masculine toughness, including the model talker's voice and face and the listener's endorsement of masculine stereotypes, additionally contribute to a less categorical perception of sibilants in these environments.