Lack of persistence when faced with challenging math problems impacts student achievement. Having taught high school math for only three years, I have observed its effect on students in my class every year. Some studies show the importance of entry points in form of questions positively contribute to a student’s spending more time, able to positively struggle during the process of problem solving which extends their thinking that, in turn, counteracts lack of persistence. The purpose of this action research was to examine different strategies used in classrooms to decrease lack of persistence leading to an entry point into a challenging math problem and spending time in problem solving. During the extended thinking framework cycle, students participated in three strategies in their lessons and activities involving asking protocol-based questions and students responding while recording each others’ responses during which they received written feedback. Data collection included pre- and post-intervention surveys student work, and observation data. Findings from the data suggested that the use of strategies that involve protocol questions when faced with challenging math problems increased students spending more time by persisting in challenging math problems.