This study evaluated the effect of multiple consecutive adhesive resin coatings of adhesive bonded to human dentin on nanoleakage and resin–dentin bond strength. Resin bonded dentin specimens were prepared using a total-etch adhesive (One-Step Plus) applied as multiple consecutive coating, or using two self-etch adhesive systems (iBond or Fluoro Bond). For the total-etch adhesive, resin application and air evaporation were performed 1, 2, 3, or 4 times. The self-etch adhesives were applied according to manufacturers’ instructions. Resin–dentin bonded beams were prepared and immersed in water (control) or ammoniacal silver nitrate. After storage, microtensile bond strengths were measured. The fractured surfaces were examined by scanning and transmission electron microscopy (SEM and TEM), and energy-dispersive X-ray spectrometry (EDX). No significant differences in bond strength were found between water and silver nitrate storage groups. Several types of silver depositions (spotted, reticular, or water trees) were found in adhesive joints. The bond strengths of the single coated specimens of the total-etch adhesive were significantly lower than those receiving 2–4 coatings. Single coats produced more nanoleakage than multiple coats. However, no correlation was found between the bond strengths and nanoleakage between the different adhesives (total-etch adhesive with different conditions or self-etch adhesives).