Background: While wearing masks during the pandemic poses communication and social challenges for people in everyday life, those with social anxiety might find them plausible, aligning with contemporary cognitive theories. Social anxiety involves fearing negative assessments and holding a negative self-image. Concealing anxiety symptoms during mask use may contribute to a more positive self-perception. Aims: Given that up to 60% of adults seeking stuttering treatment also meet criteria for social anxiety disorder, this study aims to investigate the complex relationship between communication freedom, self-perceived stuttering and anxiety in adults who stutter (AWS). The unique context of mandatory mask-wearing during the pandemic provides an opportunity to explore these dynamics and understand the conflicting relationships between stuttering, anxiety-related safety behaviours and the need for open communication in AWS. Methods and Procedures: Twenty AWS participated in interviews, responding to open-ended questions to elucidate their affective, cognitive and behavioural experiences while wearing masks during the COVID-19 pandemic. Thematic analysis was used to identify the emerging themes and subthemes based on information-rich quotes, employing a six-phase recursive process. Various speech and anxiety-related measures were used to describe the characteristics of the study participants. Outcomes and Results: Three main themes and sub-themes emerged. The first theme highlights communication challenges for AWS wearing masks, impacting verbal and nonverbal interactions. The second theme reveals AWS wearing masks to conceal stuttering cues, experiencing reduced stress. The third theme indicates that, despite the comfort in concealment, most AWS prefer speaking freely without a face mask. Conclusions and Implications: The conflict between the desire for authentic, fluent communication and the ease of hiding stuttering symptoms poses a major dilemma for AWS. According to the results of this study, most adults who stutter prioritize open communication. However, there were some individual differences. A major factor influencing their decision was their fear of negative evaluation.