Purpose: The present study evaluated the influence of air entrapment within demineralized dentin on bond strength, nanoleakage, and degree of conversion. Materials and Methods: A vacuum pump with adjustable pressure was used to control the gaseous pressure of a sealed container during the application of a two-step etch-and-rinse adhesive to demineralized dentin. Atmospheric pressure was used as control, and reduced pressures (0.08, 0.06, 0.04 MPa) as experimental variables. Simulated pulpal pressure was adopted during the bonding procedures. After making composite buildups and 24-h water storage, 48 specimens were occlusogingivally sectioned into beams for microtensile bond strength testing, interfacial morphology observation, and nanoleakage evaluation immediately (6 for each group) or after artificial aging (6 for each group); 20 specimens (5 for each group) were occlusogingivally sectioned into slices for degree of conversion testing. Failure modes were compared using the chi-squared test. The other data were analyzed using ANOVA. Results: When air within composite-dentin interface was thinned with reduced pressures, more thorough adhesive infiltration was achieved, and less distinct nanoleakage as well as higher bond strength were observed compared with control groups, regardless of artificial aging. Mixed failure was predominantly identified, and its percentage was higher in the reduced pressure groups than in the controls. Adhesive application at reduced pressure improved the degree of conversion. Conclusion: Air entrapment in the demineralized dentin adversely affects composite-dentin bonds. Adhesive application at reduced pressure is helpful for reducing entrapped air, thereby improving the durability of composite-dentin bonds. Palabras clave: vacuum, microtensile bond strength, bond durability, dentin bonding, nanoleakage, polymerization