While there are many common challenges that are experienced by all new teachers, pressures on new teachers can differ based on the context in which they work. This qualitative study aims to highlight the first-year challenges and most effective supports experienced by first-year teachers in a small Canadian public school district situated in an affluent urban area. The data for this study were collected through semi-structured private interviews with thirteen novice (in their second through sixth year) teachers who have spent the entirety of their teaching careers in this school district. Common themes include challenges with time management, work-life balance, reporting, differentiation, classroom management and teaching assignment. For a significant number of participants in this study, their first year of teaching was marked by the increased demands of the COVID-19 pandemic. Participants in this study overwhelmingly identified pressures felt from high parent expectations as a stressor and an area where they required support from administrators and colleagues. Other significant supports for challenges experienced in the first year were identified as mentorship and moral support from cross-grade colleagues, partner teachers, mentors, administrators, and other district staff. The study also found that the first-year experiences influenced their current professional practices and identities. The findings of this study add strength for the need of mentorship and induction programs and professional development opportunities that are specific to the context-based needs of new teachers- specifically those in schools where there may be increased pressures due to highly involved parent populations. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]