The objective of this paper was to evaluate and compare the quantity and sustainability of digital health initiatives in the South Asia region before and during the COVID-19 pandemic. The study used a two-step methodology of (a) descriptive analysis of digital health research articles published from 2016 to 2021 from South Asia in terms of stratification of research articles based on diseases and conditions they were developed, geography, and tasks wherein the initiative was applied and (b) a simple and replicable tool developed by authors to assess the sustainability of digital health initiatives using experimental or observational study designs. The results of the descriptive analysis highlight the following: (a) there was a 40% increase in the number of studies reported in 2020 when compared to 2019; (b) the three most common areas wherein substantive digital health research has been focused are health systems strengthening, ophthalmic disorders, and COVID-19; and (c) remote consultation, health information delivery, and clinical decision support systems are the top three commonly developed tools. We developed and estimated the inter-rater operability of the sustainability assessment tool ascertained with a Kappa value of 0.806 (±0.088). We conclude that the COVID-19 pandemic has had a positive impact on digital health research with an improvement in the number of digital health initiatives and an improvement in the sustainability score of studies published during the COVID-19 pandemic.