This study assessed the impact of both applied and incidental moisture management strategies in two Cross-Laminated Timber (CLT) buildings. The evaluation involved analysing project specifications, technical drawings, and procurement documents, supplemented by data collection from field studies. In the first building, the measured moisture content (MC) ranged from 9% to 18% in areas where the end-grain protection of the CLT panels remained intact. However, there were also areas where the end-grain surface protection was probably damaged and higher MC was reported there. In the second building, the MC varied from 12% to 18% in first-floor panels with functional end-grain protection, while second-floor panels without such protection exhibited MC levels as high as 40%. Localised damage to end-grain protection was identified as the cause of moisture safety issues in the first building. In the second building, the elevated MC in the second-floor panels necessitated mechanically aided moisture dry-out. The study concluded that readiness to mitigate moisture problems is essential, irrespective of the protection method employed against water ingress. Prolonged exposure to outdoor air, even under temporary weather protection, increased MC in the first building; however, the temporary weather protection effectively shielded against rain. Undamaged end-grain protection was also found to be effective. The assumption that contractor experience and a robust moisture strategy alone guarantee moisture safety was proven unfounded. The outcomes are dependent upon the quality of design and planning. Therefore, it is recommended to include specific moisture safety drawings and a comprehensive moisture safety strategy analysis within the building design.