Independent living care for polypharmacy patients can be complicated in those situations with medications that are pro re nata (PRN, “as needed”). Such medication regimen may involve multiple dosing whereby specific drug contraindications might be easily overlooked by hospice and palliative care patients, or by those isolated and not in regular contact with care providers. The goal of this paper is to describe the development steps and current design of a system providing medication decision support for isolated patients. With an increased number of patients living alone or isolated - a situation exacerbated during the COVID19 pandemic – polypharmacy patients may be challenged when PRN (as needed) medications confound what might ordinarily be a routine medication schedule. Central to our medication management system design is the so-called “conversational agent” that when integrated with a natural language processing front- end and classification tree algorithm provide a dynamic framework for patient self-management of medications. Research on “patient need” revealed patients were more likely to embrace the system if the system were autonomous, secure, and not cloud-based.