Reusable elastomeric half-mask respirators (EHMR) are an alternative to address shortages of disposable respirators. While respirator discomfort has been noted as a barrier to adherence to wearing an N95 filtering facepiece respirator (FFR) among health care personnel (HCP), few have examined EHMR comfort while providing patient care, which was the purpose of this study. Among a cohort of 183 HCP, we prospectively examined how HCP rated EHMR tolerability using the Respirator Comfort, Wearing Experience, and Function Instrument (R-COMFI) questionnaire at Study Week 2 and Week 10. At the completion of the study (Week-12), HCP compared EHMR comfort with their prior N95 FFR use. Overall R-COMFI scores and three subscales (comfort, wear experience, and function) were examined as well as individual item scores. The HCP reported an improved overall R-COMFI score (lower score more favorable, 30.0 vs. 28.7/47, respectively) from Week 2 to Week 10. Many individual item scores improved or remained low over this period, except difficulty communicating with patients and coworkers. The overall R-COMFI scores for the EHMR were more favorable than for the N95 FFR (33.7 vs. 37.4, respectively), with a large proportion of workers indicating their perception that EHMR fit better, provided better protection, and they preferred to wear it in pandemic conditions compared with the N95 FFR. Findings suggest that the EHMR is a feasible respiratory protection device with respect to tolerance. EHMRs can be considered as a possible alternative to the N95 FFR in the health care setting. Future work is needed in the EHMR design to improve communication.