Multiple different approaches to the brachial plexus are available for the regional anesthesiologist to provide successful anesthesia and analgesia for ambulatory surgery of the upper extremity. Although supraclavicular and infraclavicular blocks are faster to perform than axillary blocks, the operator needs to keep in mind that blocks performed around the clavicle carry the risk for specific side effects and complications, no matter whether ultrasound or nerve stimulation is the chosen modality for neurolocation. Owing to the ambulatory nature of the planned surgical intervention, even significant side effects may not become clinically symptomatic until the patient is discharged from the facility. For example, due to pneumothorax risks, axillary or mid-humeral blocks remain the most logical approaches for ambulatory surgical procedures at and below the elbow, while reserving infra-clavicularor supraclavicular approaches for surgery from the proximal humerus to above the elbow. Smaller interventions such as carpal tunnel release or trigger finger release can be performed under elbow, wrist, or digital blocks. The regional anesthesiologist should strive to develop a tailored plan for each individual case to provide the most effective and safest nerve block technique for their patients.