Background: Acute hospital readmission of older adults receiving hospice care is not aligned with hospice goals. Objective: To identify factors associated with 30-day readmission among older adults newly discharged to hospice. Design/Subjects: Medical record review of 59 patients, 19 readmitted within 30 days and 40 randomly selected controls not readmitted, from 206 patients newly discharged to home hospice care between February 1, 2005 and January 31, 2010. Measures/Analysis: Information was collected about hospital course, end-of-life planning, and posthospitalization follow-up. We calculated bivariate associations and developed a Cox Proportional Hazards model examining the relation between index admission characteristics and readmission. Results: Patients' mean age was 79.7 -8.4; 74.6% were female; 52.5% were black. Among those readmitted, 25% had received a palliative care consultation, compared to 47.1% of those not readmitted ( p = 0.06). Patients without a participating decision-maker involved in their hospice decision had 3.5 times the risk of readmission within 30 days, compared to those with (hazard ratio [HR] 3.53, confidence interval [CI] 0.97, 12.82). Patients who had one or more telephone contacts with their primary care physician (PCP) during week 1 after discharge had 2.4 times the readmission risk within 30 days, compared to patients with no such contacts during this period (HR 2.35, CI 0.9, 6.1). Conclusions: Readmission within 30 days of initial discharge to hospice is associated with several measures of care and care planning. Further study of these measures may identify opportunities for interventions to improve the hospital-to-hospice transition and to decrease hospital readmissions.