This paper reports on the development of complex unfamiliar mathematics questions using conventional mathematics questions. The autoethnographic research data included retrospective reflections of two educators and review of literature. Data analysis resulted in a three-phase development process: identifying conventional questions and subject matter to be modified to enhance levels of understandings and skills, modifying conventional questions and subject matter to complex unfamiliar questions, and identifying enhanced understandings and skills in modified questions. The paper then discusses the educators' insights developing complex unfamiliar mathematics questions for the practice of teaching and learning.