Accelerated by the adoption of remote monitoring during the COVID-19 pandemic, interest in using digitally captured behavioral data to predict patient outcomes has grown; however, it is unclear how feasible digital phenotyping studies may be in patients with recent ischemic stroke or transient ischemic attack. In this perspective, we present participant feedback and relevant smartphone data metrics suggesting that digital phenotyping of post-stroke depression is feasible. Additionally, we proffer thoughtful considerations for designing feasible real-world study protocols tracking cerebrovascular dysfunction with smartphone sensors.