This collaborative action research project was conducted in a second-grade classroom to determine the impact that digital web-based tools would have in helping a school media coordinator scaffold her students' understanding of productive versus nonproductive questions. The digital tools Kahoot, Quizizz, and Socrative were used by the students to help them recognize the difference between productive and nonproductive questions, as well as support them in the ability to generate their own productive questions. While results related to student learning outcomes showed minimal increases, the iterative and reflective nature of the action research cycle enabled the media coordinator and researcher to refine their original choices of digital technology, based on formative assessment in the action research cycle, to select the digital tools that best fit the context of this specific learning environment. These findings offer further support for the use of collaborative action research as a means to assist educators in choosing the right digital tools to meet their students' learning needs.