Subdural anesthesia and spinal subdural hematoma are rare complications of combined spinal-epidural anesthesia. We present a patient who developed both after multiple attempts to achieve combined spinal-epidural anesthesia. A 21-year-old parturient, gravida 1, para 1, with twin pregnancy at gestational age 34+ 5 weeks underwent cesarean delivery. Routine combined spinal-epidural anesthesia was planned; however, no cerebrospinal fluid outflow was achieved after several attempts. Bupivacaine (2.5 mL) administered via a spinal needle only achieved asymmetric blockade of the lower extremities, reaching T12. Then, epidural administration of low-dose 2-chlorprocaine caused unexpected blockade above T2 as well as tinnitus, dyspnea, and inability to speak. The patient was intubated, and the twins were delivered. Ten minutes after the operation, the patient was awake with normal tidal volume. The endotracheal tube was removed, and she was transferred to the intensive care unit for further observation. Postoperative magnetic resonance imaging suggested a spinal subdural hematoma extending from T12 to the cauda equina. Sensory and motor function completely recovered 5 h after surgery. She denied headache, low back pain, or other neurologic deficit. The patient was discharged 6 days after surgery. One month later, repeat MRI was normal. All anesthesiologists should be aware of the possibility of SSDH and subdural block when performing neuraxial anesthesia, especially in patients in whom puncture is difficult. Less traumatic methods of achieving anesthesia, such as epidural anesthesia, single-shot spinal anesthesia, or general anesthesia should be considered in these patients. Furthermore, vital signs and neurologic function should be closely monitored during and after surgery.