Background: The influence of the listening environment in which communication occurs has been of longstanding interest related to communication disorders. It also has been posited that specific listening scenarios may differentially effect listener judgements of a speaker. In the case of those who have lost their larynx and normal voice due to cancer, a listener's assessment may carry a substantial penalty. This study was designed to determine if situationally-bound communication 'scenario' influences a listener's auditory-perceptual judgement of level of comfort for three modes of postlaryngectomy alaryngeal speech: oesophageal (ES), tracheo-oesophageal (TE) and electrolaryngeal (EL) speech. Additionally, a modified oesophageal speech (MES) group where air insufflation pauses were excluded digitally, was also included; this modification was employed to reduce the potential impact of unusual, non-junctural pauses that may occur in some oesophageal speakers. Methods and Procedures: Forty-eight speaker samples (12 speakers per alaryngeal group) were evaluated by 22 naïve adult listeners for a dimension termed listener comfort (LC). Judgements assessed all speaker samples based on two implied listening scenarios: (1) a social conversation interaction (LC-Soc) and (2) a telephone conversation (LC-Tel). Both scenarios were rated by listeners using a visual analogue scaling procedure. Ratings were provided in a counterbalanced manner across two sessions separated by 7-10 days. Outcomes and Results: Listener ratings were not found to differ significantly by listening scenario (social vs. telephone) for any given speech mode. However, significant differences were observed in listener judgements of TE speakers when compared to EL, ES and MES speaker samples for both LC-Soc and LC-Tel listening scenarios. Further, a significant correlation was found between judgements of LC-Soc and LC-Tel, indicating a strong relationship between the two. Conclusions and Implications: Listeners indicated that they were more comfortable listening to TE speakers when compared to the other postlaryngectomy speech modes that were evaluated. This suggests that in general, a listener's perceived LC may be more favourable to TE speech. Thus, these comparative findings provide objective data on how a listener may respond to postlaryngectomy communication methods and, consequently, may offer valuable insights into the relative merits of these postlaryngectomy communication rehabilitation methods. Collectively, the findings of this study add important information that can assist in both pre- and postoperative counselling for those who undergo laryngectomy.