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To determine how well healthcare proxies (HCPs) understand do-not-hospitalize (DNH) orders and why they may or may not initiate them.Semistructured qualitative interviews.Two nursing homes in western Massachusetts.HCPs of nursing home residents with advanced dementia.In-depth interviews were audiotaped and transcribed verbatim. Data were qualitatively analyzed in an iterative process, and emergent concepts were conceptually ordered into explanatory categories. Pertinent demographic and clinical information was collected from the Minimum Data Set (MDS) and patient charts.Sixteen of 31 eligible HCPs were interviewed. Major findings included barriers to and facilitators of initiating DNH orders. Barriers included a perceived lack of physician involvement in decision-making and limited understanding of DNH orders and the resident's prognosis. Facilitators included a HCPs' personal experience in health care, understanding the prognosis of advanced dementia, and a desire to limit resident distress.The potential barriers to and facilitators of HCPs initiating DNH orders identified in this study suggest that HCPs may benefit from more in-depth discussions with healthcare providers when making this decision. Interventions to address these barriers may improve the capacity of HCPs to make informed decisions about DNH orders that reflect individuals' values and wishes. J Am Geriatr Soc 61:1568–1573, 2013.