The purpose of this study is to understand how selected insurance practitioners learn and developed in their practices setting. The selected insurance practitioners (collectively customer service representatives, insurance agents, and risk managers) are responsible for the counseling and placement of insurance products and the implementation of alternative risk funding mechanisms for individuals and business organizations. A qualitative comparative case study was undertaken in which 30 practitioners from 3 different occupational categories were interviewed to discover factors, criteria, strategies and influences affecting their continuing professional education (CPE). A critical incident technique was utilized to elicit information on each selected insurance practitioner's decision making processes. Schon's theory of reflective practice was used to analyze each practitioner's reflective processes in confronting a practice setting dilemma. The five primary themes that emerged are: CPE is self-selected with little assurance of quality; CPE is not aligned with organizational goals; practitioners have broad disparities in educational level; factors affecting CPE differ by practitioner category; and, educational level and industry certifications promote reflection. Nine recommendations are made by the researcher in an effort to promote the quality and competence of insurance and risk management practitioners. These recommendations are: implement a structured orientation; develop a positive professional environment; develop career paths that are aligned with strategic goals; promote practitioner education; promote internships and mentoring programs; promote quality in CPE; encourage involvement in professional associations; promote continuing professional development; and, strengthen state licensing standards. [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://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]