OBJECTIVE: This report describes the case of a 76-year-old male who developed an upper gastrointestinal bleed shortly after beginning megestrol acetate (MGA) to treat geriatric failure to thrive (GFTT). He was also taking rivaroxaban for stroke prevention because of atrial fibrillation but had a low risk of bleeding. This article aims to provide the reader with an overview of MGA's impact on hemostasis, as well as a review of therapeutics on appetite stimulants and important transitions of care considerations for GFTT.<br/> SETTING: The primary setting was a community teaching hospital in Florida. The patient had many transitions of care, including hospital-to-skilled nursing facility and then a hospital readmission for the primary problem reported here. A skilled nursing facility medication administration record and outpatient community pharmacy were the primary sources of the patient's admission and discharge medication histories.<br/> PRACTICE CONSIDERATIONS: MGA's published labeling supports a prothrombotic mechanism; however, its pharmacology may also confer anticoagulant properties. This may lead to potential drug-drug interactions in patients on concomitant anticoagulant therapy. There is weak evidence supporting appetite stimulants in GFTT, and transitions of care in this population is especially important because of these patients' frequent care continuum contact.<br/> CONCLUSIONS: MGA, a synthetic derivative of endogenous progesterone used to treat GFTT, may exert either prothrombotic or anticoagulant effects, and as such potential for drug interactions with anticoagulants must be considered. Patients taking MGA should be closely monitored for coagulation changes throughout transitions of care.