The objective of this study was to examine the effect of different conditions of simulated hydrostatic pulpal pressure on the μTBS of HEMA-based and HEMA-free dentin bonding agents (DBAs). The influence of dentin location (deep and superficial) on μTBS was also evaluated. Flat coronal dentin surfaces of extracted human molars were prepared. Three groups of resin-bonded specimens were exposed to different pulpal pressures. Pulpal pressure was maintained for 20 min for each group. A flowable resin composite was used for coronal build-up. The bonded teeth were sectioned and, after 24 h of water storage, stressed to failure using the microtensile tester (μTBS). Failed samples were analyzed by SEM inspection. HEMA-based DBAs were much more sensitive to pulpal pressure conditions than non-HEMA-containing DBAs. Pulpal pressure had a greater influence in deep dentin. The HEMA-free DBA was insensitive to the presence or absence of pulpal pressure condition. SEM inspection confirmed a relationship between the presence of voids inside the HEMA-based DBAs layer and the lower μTBS results. HEMA-based DBAs are more sensitive to pulpal pressure conditions than HEMA-free DBAs. Interestingly, HEMA-free DBA showed a greater number of water droplets at resin-dentin interface in all tested conditions.