Distressing symptoms are associated with poor function, acute care use, and mortality in older adults. The number of older jail inmates is increasing rapidly, prompting calls to develop systems of care to meet their healthcare needs, yet little is known about multidimensional symptom burden in this population. This cross-sectional study describes the prevalence and factors associated with distressing symptoms and the overlap between different forms of symptom distress in 125 older jail inmates in an urban county jail. Physical distress was assessed using the Memorial Symptom Assessment Scale. Several other forms of symptom distress were also examined, including psychological (Generalized Anxiety Disorder Scale, Patient Health Questionnaire), existential (Patient Dignity Inventory), and social (Three Item Loneliness Scale). Information was collected on participant sociodemographic characteristics, multimorbidity, serious mental illness (SMI), functional impairment, and behavioral health risk factors through self-report and chart review. Chi-square tests were used to identify factors associated with physical distress. Overlap between forms of distress was evaluated using set theory analysis. Overall, many participants (74%) reported distressing symptoms, including having one or more physical (44%), psychological (37%), existential (54%), or social (45%) symptoms. Physical distress was associated with poor health (multimorbidity, functional impairment, SMI) and low income. Of the 93 participants with any symptom, 49% reported three or more forms of distress. These findings suggest that an optimal model of care for this population would include a geriatrics-palliative care approach that integrates the management of all forms of symptom distress into a comprehensive treatment paradigm stretching from jail to the community.