Obscure gastrointestinal bleeding (OGIB) can present as a diagnostic dilemma and management can be challenging. The search for causes of OGIB is usually centered on visualizing the small bowel, and in the past decade, the technology to visualize the entire small bowel has significantly advanced. Moreover, small bowel endoscopic imaging has replaced, in many instances, prior radiographic evaluation for obscure GI bleeding. These new modalities, such as small bowel capsule endoscopy (CE), balloon-assisted deep enteroscopy [double balloon enteroscopy (DBE) and single balloon enteroscopy (SBE)], and overtube-assisted deep enteroscopy (spiral enteroscopy), are paving the way toward more accurately identifying and treating patients with OGIB. We will review the diagnostic modalities available in evaluating a patient with OGIB and also propose the management based on clinical and endoscopic findings.