The newly discovered respiratory disease, COVID-19, has caused significant physical and psychological strain for frontline healthcare providers (HCPs). Researchers have found higher levels of anxiety, stress, depression, and poor sleep quality in HCPs during this time. It is crucial to ensure the well-being of HCPs to secure a functioning health system amid a pandemic. This work explores how HCPs might interact with a Just-in-Time Adaptive Intervention (JITAI) system that collects their biopsychosocial metrics using off-the-shelf fitness trackers and ecological momentary assessments (EMAs) for providing actionable interventions in real-time. We found that different healthcare-related life factors influenced our participant HCPs’ engagement with the technological tools in the study. HCPs also expressed the need for better tools to help them convey their emotional exhaustion from a year-long pandemic. We also observed that HCPs sometimes could not maintain their psychological well-being due to other external factors, especially workload. These findings point to important design requirements for JITAIs to support frontline providers’ psychological well-being, both within healthcare and beyond.