Acute low back pain, radiculopathy, and associated disabilities have a prevalence of 2% in the United States, which represents a significant health problem and a major cause of workplace absence. The condition primarily affects 25- to 45-year-old men and women. Epidural steroid injections (ESIs) are commonly administered to relieve this pain and improve mobility without surgery. This case report presents issues related to the treatment of an epidural hematoma in an 87-year-old man receiving long-term anticoagulant therapy. It reviews the risks, benefits, side effects, complications, and contraindications to ESI and the American Society of Regional Anesthesia consensus recommendations for the performance of neuraxial procedures in patients receiving anticoagulant therapy. It is imperative that any provider who performs ESIs know the risks, benefits, complications, and contraindications for this procedure. Practitioners must also be able to recognize and manage or appropriately refer patients having immediate or delayed complications related to the placement of an ESI.