In this study, the failure mechanism of sandwich-to-laminate T-joints under pull-off loading was investigated by experiment and the finite element method. A total of 26 T-joint specimens were manufactured and tested in order to investigate the effects of both adhesive thickness (0.4, 2.0, and 4.0 mm) and environmental conditions on the failure of the joints. The results showed that failure occurred mainly as intralaminar failure in the first layer of the sandwich face, which was contacted to the paste adhesive. The failure load did not significantly change with increasing adhesive thickness in both RTD (Room Temperature and Dry) and ETW (Elevated Temperature and Wet) conditions. In the case of ETW conditions, however, the failure load increased slightly with an increase in adhesive thickness. The joints tested in ETW conditions had higher failure loads than those tested in RTD conditions. In addition to the experiment, a finite element analysis was also conducted to investigate the failure of the joint. The stress inside the first ply of the sandwich face was of interest because during the experiment, failure always occurred there. The analysis results showed good agreement with the trend of experimental results, except for the case of the smallest adhesive thickness. The highest stress was predicted in the regions where initial failure was observed in the experiment. The maximum stress was almost constant when the adhesive thickness was beyond 2 mm.