Solicited journal entries are a qualitative research method with a fairly strong tradition in sociological research and particularly in qualitative health research. However, the practices and strengths associated with solicited journal entries have not been explored as frequently or comprehensively as more conventional qualitative research methods, such as interviews. During the COVID-19 pandemic we carried out two online studies employing solicited written journal entries and photos. One study focused on pregnancy and health care experiences during the pandemic and the other on everyday life while working from home due to public health restrictions. Here, we discuss solicited online journal entries as a qualitative method and reflect on the strengths and challenges we encountered, including those related to using the online survey tool LimeSurvey for a qualitative diary-based study. The richness of data and the ability to solicit participants’ contemporaneous reflections over the course of a set length of time, the ability to reach people across time zones and in multiple places, and the ability to adapt prompts in a quickly changing research context are major strengths of online journaling. The level of commitment required by participants, the potential for attrition, the need for literacy and technology access, and the large amount of data from each participant are potential limitations for researchers to consider.