Providing various levels of sedation to pediatric patients undergoing invasive, complex, and otherwise painful dental procedures involves a multifactorial level of anesthetic treatment planning. Numerous considerations, including intraoperative oral bleeding, significant surgical stimulation, and impaired access to the pediatric airway are potential hazards and increase risks when performing these procedures outside of traditional, high-resource hospital operating room settings. Judicious administration of local anesthesia intraorally and to the surrounding oral cavity can facilitate surgery and reduce the anesthetic and analgesic demands in the perioperative and postoperative period as well. However, with the close proximity of the intraoral surgical field to the pediatric airway, precautions are required in the assessment and pre-operative phase to ensure these types of dental procedures are accomplished with relative safety in nontraditional settings. Despite other chapters exhaustively covering the important aspects of preoperative evaluation and pharmacologic strategies used in dental sedation, this chapter will explore some of the more common painful and invasive pediatric dental procedures with accompanying precautions and specific sedation and anesthetic considerations.