Background/Objectives: Eversion carotid endarterectomy (CEA) in awake patients is performed using cervical plexus blocks (CPBs) with or without carotid artery sheath infiltration (CASI) under ultrasound guidance. Although adequacy of anesthesia (AoA) guidance monitors nociception/antinociception balance, its impact on intraoperative analgesia quality and perioperative outcomes in awake CEA remains unexplored. Existing literature lacks evidence on whether AoA-guided anesthesia enhances clinical outcomes over standard techniques. This study aimed to assess the role of AoA guidance in improving intraoperative analgesia and perioperative outcomes in patients undergoing CEA with CPBs alone or with CASI compared to standard practice. Methods: A randomized controlled trial included 184 patients divided into three groups: CPBs with intravenous rescue fentanyl (IRF) and lidocaine (LID) guided by hemodynamic observation (C group), AoA-guided IRF and LID (AoA group), and AoA-guided IRF, LID, and CASI (AoA-CASI group). Primary outcomes included perioperative adverse events, and secondary outcomes assessed rescue medication demand and hemodynamic stability. Results: Analysis of 172 patients revealed no significant differences between groups in perioperative adverse events or hemodynamic parameters (p > 0.05). However, the AoA-CASI group demonstrated significantly reduced IRF and LID usage compared to the C and AoA groups (p < 0.001). No significant advantage was observed between the AoA and C groups regarding adverse events (p = 0.1). Conclusions: AoA-guided anesthesia with or without CASI does not significantly reduce perioperative adverse events or improve hemodynamic stability in awake CEA. Clinical implications suggest that focusing on surgical technique optimization may yield greater benefits in reducing adverse events compared to advanced anesthetic monitoring. Further studies are warranted to explore alternative approaches to enhance clinical outcomes.