This study aimed to use quantitative and qualitative evaluations based on micro-tensile bond strength (μTBS) to clarify the appropriate immediate dentin sealing (IDS) approach for improving the bonding of CAD/CAM ceramic crown restorations. Forty-eight extracted human molars were prepared to obtain standardized abutment specimens and divided into three groups: no IDS (group C: control), IDS performed by a single application of an all-in-one adhesive system (group A), and IDS performed by the combined application of an adhesive system and a flowable resin composite (group F). All specimens were restored with a ceramic crown fabricated by a chair-side CAD/CAM system and were divided into no-stress and stressed groups. After cyclic loading (78.5 N; total, 3 × 105 cycles; 90 cycles/min) on the specimens in the stressed group, all specimens were sectioned. The μTBS values for the occlusal and mesioaxial walls were measured (n = 16) and analyzed statistically. The quantitative bonding performance of groups A and F were superior to that of group C, regardless of the cyclic loading and abutment wall conditions. Group F showed the maximum bond strength and the highest bond durability in the qualitative bonding performance even under the cyclic loading condition simulating clinical mastication.