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As mathematics education has evolved to focus on conceptual learning, math teachers need professional development that provides the ability to engage collaboratively and reflectively. This paper reports on an online math professional development workshop series designed to support teacher collaboration and reflective practices through engagement in problem solving and investigation of various solution paths. Through analysis of workshop data, a three-part categorization of reflection comments as Developed, Developing, and Starting has emerged. This categorization demonstrates that the collaborative problem-solving process within the workshop encourages teachers to reflect thoroughly about their own mathematical thinking and by extension, the mathematical thinking of their peers. Thus, the workshops support teachers’ ability to be students-centered and focused more on mathematical processes and mathematical thinking.