Background. Hypoglycemia (HG) causes symptoms, can be fatal, and confers risk of dementia. Wearable devices can improve measurement and feedback to patients and clinicians about HG events and risk. Objectives. Determine whether vulnerable older adults could use wearables, and explore HG frequency over two weeks. Methods. First, ten participants with diabetes mellitus piloted a continuous glucometer, physical activity monitor, electronic medication bottles, and smartphones facilitating prompts about medications, behaviors, and symptoms. They reviewed graphs of glucose values, and were asked about the monitoring experience. Next, a larger sample (N=70) wore glucometers and activity monitors, and used the smartphone and bottles, for two weeks. Participants provided feedback about the devices. Descriptive statistics summarized demographics, baseline experiences, behaviors, and HG. Results. In the initial pilot, ten patients aged 50 to 85 participated. Problems addressed included failure of the glucometer adhesive. Patients sought understanding of graphs, often requiring some assistance with interpretation. Among 70 patients in subsequent testing, 67% were African-American; 59% were women. Nearly one-fourth (23%) indicated that they never check their blood sugars. Previous HG was reported by 67%. In two weeks of monitoring, 73% had HG (glucose ≤ 70 mg/dL), and 42% had serious, clinically significant HG (glucose under 54 mg/dL). Eight patients with HG also had HG by home-based blood glucometry. Nearly a third of daytime prompts were unanswered. In 24% of participants, continuous glucometers became detached. Conclusions. Continuous glucometry occurred for two weeks in an older vulnerable population, but devices posed wearability challenges. Most patients experienced HG, often serious in magnitude. This suggests important opportunities to improve wearability and decrease HG frequency among this population.