This study analysed flexural properties, microhardness, and the degree of conversion (DC) of five bulk-fill composites under clinically relevant conditions (4 mm thick specimens) in comparison to 2 mm specimens according to ISO 4049. Additionally, the effect of rapid polymerisation on 4 mm specimens was evaluated after accelerated aging. DC was measured using Fourier transform infrared spectrometry at 2 and 4 mm thick layers, while flexural properties and Vickers microhardness were tested using 16 × 2 × 2 mm or 16 × 2 × 4 mm specimens. Three polymerisation protocols were used: (I) “ISO”: 2 mm thickness, 1000 mW/cm2, double-sided; (II) “10 s”: 4 mm thickness, 1000 mW/cm2, one-sided; and (III) “3 s”: 4 mm thickness, 2600 mW/cm2, one-sided. Mechanical properties were tested after 1 day, after 10,000 thermocycles, and after 10,000 thermocycles followed by a 7-day immersion in absolute ethanol. The “ISO” protocol produced a higher DC and microhardness of all materials. Elastic modulus was significantly higher for the “ISO” protocol compared to the 4 mm specimens. The differences in flexural strength for all polymerisation protocols were equalised after thermocycling and immersion in absolute ethanol. All tested materials met the ISO 4049 flexural strength requirement (80 MPa) for all polymerisation methods and all aging conditions. Rapid polymerisation achieved nearly optimal properties (ISO), except for elastic modulus, which was significantly reduced in 4 mm samples.