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This research addresses key uncertainties in building energy performance arising from inadequate representation of thermal bridging and moisture transfer in envelope detailing. Analysis revealed that structural elements increased heat gains by 10–12%, doubling the façade's effective U-value. Adding insulation to mitigate these bridges reduced peak envelope loads by 29% and lowered cooling demand by 20 TR. Over three years, insulation's thermal conductivity varied by up to 83% due to moisture accumulation, impacting long-term performance. This study proposes a detailed workflow integrating hygrothermal behavior into simulations, enabling designers and consultants to conduct realistic assessments and recommend durable, energy-efficient envelope solutions.