Abstract Background Cognitive interviewing is a well-established qualitative method used to develop and refine PRO measures. A range of digital technologies including phone, web conferencing, and electronic survey platforms can be leveraged to support the conduct of cognitive interviewing in both children and adults. These technologies offer a potential solution to enrolling underrepresented populations, including those with rare conditions, functional limitations and geographic or socioeconomic barriers. In the aftermath of the COVID-19 pandemic, the use of digital technologies for qualitative interviewing will remain essential. However, there is limited guidance about adapting cognitive interviewing procedures to allow for remote data capture, especially with children. Methods Synthesizing the literature and our research experiences during the COVID-19 pandemic, we examine considerations for implementing digitally supported cognitive interviews with children, adolescents, and adults. We offer recommendations to optimize data quality and empirical rigor and illustrate the application of these recommendations in an ongoing cognitive interviewing study to develop and refine a new pediatric PRO measure. Results Good research practices must address participant and researcher preparation for study-related procedures and should anticipate and pre-emptively manage technological barriers. Field notes should detail interview context, audio/video cues, and any impact of technological difficulties on data quality. The approaches we recommend have been tested in an ongoing cognitive interviewing study that is enrolling children/adolescents with cGVHD ages 5–17 and their caregivers [NCT 04044365]. The combined use of telephone and videoconferencing to conduct cognitive interviews remotely is feasible and acceptable and yields meaningful data to improve the content validity of our new PRO measure of cGVHD symptom bother. Conclusion Digitally supported cognitive interviewing procedures will be increasingly employed. Remote data collection can accelerate accrual, particularly in multi-site studies, and may allow for interviewer personnel and data management to be centralized within a coordinating center, thus conserving resources. Research is needed to further test and refine techniques for remote cognitive interviewing, particularly in traditionally underrepresented populations, including children and non-English speakers. Expansion of international standards to address digitally supported remote qualitative data capture appears warranted.