This qualitative case study focused on understanding teachers' perceptions of technology-based professional development sessions and the impact of technology requirements on their decisions to remain in or exit the teaching profession. The study involved seven middle school teachers with varying teaching experience and technology backgrounds. Participants shared their insights through journals, interviews, and document notes, which were then organized into themes reflecting their responses to the research questions. The findings revealed key themes such as the structure and availability of professional learning sessions, facilitators' positive impact, teachers' emotions during and after training, optional learning strategies, and how these factors influence the decision to stay in or leave the teaching profession. Participants highlighted challenges with the pace and content of training sessions, the role of facilitators in enhancing learning experiences, and the importance of informal collaboration in improving technology integration. Overall, participants expressed diverse perspectives on the impact of technology training, with some feeling confident implementing technology requirements while others highlighted feelings of inadequacy. The study underscores the need for tailored and supportive professional development structures to enhance teachers' proficiency and confidence in using technology tools. However, technology requirements did not influence retention in the teaching profession. [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.]