Palliative care offers undeniable advantages to elderly patients with multiple chronic illnesses in managed long-term care. However, only approximately 14% of those who require palliative care actually receive it. To investigate factors influencing decision-making regarding palliative care acceptance, and healthcare providers' communication strategies, which patients or family caregivers perceive during managed long-term care. Qualitative thematic content analysis study. Two data sources from home and community-based health care organization in a metropolitical city in the Northeastern United States were used: (a) retrospectively collected 79 phone call audio recordings between patients and/or family caregivers with healthcare providers when initiate palliative care option, and (b) prospectively collected 10 exploratory qualitative interviews with patients and/or family caregivers for this study purpose. From a total of 89 conversations, 7 themes emerged during palliative care decision-making: (a) capability for self-management; (b) symptom severity; (c) perceptions of chronic disease; (d) satisfaction with current health services; (e) code status; (f) caregiver burden and (g) other reasons, including financial considerations and service affiliations. In addition, from 10 qualitative interviews, 4 key themes in healthcare providers' communication that optimize palliative care conversations were indicated: (i) trust and relationship dynamics; (ii) positive reinforcement and personal connection; (iii) conversation setting and initiator; and (iv) collaborative approach to care coordination. Enhancing decision-making around palliative care and improving acceptance of palliative care services may be improved through the integration of personalized care plans, empathetic communication, use of symptom-inclusive assessments for timely care, and proactively addressing caregiver burden.