In the assembly process of aerospace parts, drilling is essential for carbon fiber-reinforced materials. However, due to the extreme thermal sensitivity of these composites, continuous drilling often leads to irreparable defects such as hole wall burns and exit delamination caused by concentrated cutting heat, resulting in the scrapping of parts. To address this issue, this paper explores the impact of temperature characteristics on drilling quality, providing guidance for optimizing the composite drilling process. A simulation model for single and continuous drilling was established to analyze the temperature distribution on the tool surface during drilling. A drilling temperature measurement system based on thin-film thermocouple technology was developed, enabling real-time online temperature monitoring. Continuous drilling experiments were conducted, analyzing the correlation between maximum drilling temperature and hole quality. Results show that temperatures from −25.75 °C to −9.75 °C and from 182 °C to 200.75 °C cause significant exit damage, while optimal hole quality is achieved between −1.25 °C and 168 °C.