This paper proposes a novel approach for monitoring multi-bolt looseness using guided waves and the cross-correlation of the wavelet energy envelope. By assessing variations in the wave packet, the looseness in multi-bolt assemblies can be estimated. First, the dispersion effects of Lamb waves were theoretically analyzed using the Rayleigh-Lamb equation. Next, the wavelet energy was derived through wavelet transform, and the Lamb wave envelope was obtained as a criterion for accurately separating the wave packet. Cross-correlation analysis was employed to quantitatively evaluate the dispersion of wave packets for varying levels of bolt looseness. A looseness index, termed the normalized decorrelation coefficient of wavelet energy (NDCWE), was defined. Then, validation experiments were conducted using a joint with five M8 bolts, each tightened to a standard torque of 42 N·m. Two piezoelectric transducers were attached to the periphery of the bolt group. Three preload conditions were tested for each bolt: fully tightened, 80% of the standard torque, and 10% of the standard torque, corresponding to no looseness (NL), minor looseness (ML), and significant looseness (SL), respectively. Results showed that when significant looseness occurs, the NDCWE value exceeds 0.4, confirming the effectiveness of NDCWE in detecting substantial reductions in bolt preload. Experiments assessing the effect of temperature revealed that temperature has a negligible effect on the waveforms of the S0 and A0 mode waves. Finally, to quantitatively evaluate the efficiency of the ultrasonic transducers, the bolt-to-sensor ratio (BSR) was introduced. In this study, the BSR reached 2.5, indicating that a single piezoelectric transducer can monitor the preload of 2.5 bolts. The proposed approach shows great potential for multi-bolt looseness monitoring.