Background: The health measures imposed by COVID-19 on workplaces created adverse communication settings. Our cross-sectional study aimed to document the nature and severity of the vocal difficulties experienced by educational professionals a few weeks after the implementation of health measures in schools and early childhood settings in Quebec, Canada while teaching in class. Methods: To this end, we conducted a self-report survey containing nine close-ended questions and one open-ended question regarding self-reported vocal difficulties and the implementation of health measures. The survey was answered by 194 educational professionals in October 2020. Results: Since the introduction of the health measures, respondents reported often or always: having difficulty making themselves heard (66.5%), needing to strain their voice (68.1%), having throat pain after work (38.1%), and being concerned about their vocal health (25.2%). 35.6% perceived that their voice changed moderately or a lot and 75.3% did not feel equipped to take care of their vocal health. Fisher's exact tests revealed the difficulties overall were more present in women (p < 0.05). Discussion: The qualitative analysis of open-ended question answers shows a circular process at play, where the vocal responses to the COVID-19-induced communication barriers contribute to creating more problematic communication settings, thus increasing the challenges for vocal health. Better equipping the professionals to take care of their vocal health by developing resources in their professional settings to help them face vocal challenges in both every day as well as extreme situations, should be a priority.