The purpose of this study was to measure the threshold diameter of calcifications and masses for 2D imaging, digital breast tomosynthesis (DBT), and synthetic 2D images, for a range of breast glandularities. This study shows the limits of detection for each of the technologies and the strengths and weaknesses of each in terms of visualizing the radiological features of small cancers. Mathematical voxel breast phantoms with glandularities by volume of 9%, 18%, and 30% with a thickness of 53mm were created. Simulated ill-defined masses and calcification clusters with a range of diameters were inserted into some of these breast models. The imaging characteristics of a Siemens Inspiration X-ray system were measured for a 29kV, tungsten/rhodium anode/filter combination. Ray tracing through the breast models was undertaken to create simulated 2D and DBT projection images. These were then modified to adjust the image sharpness, and to add scatter and noise. The mean glandular doses for the images were 1.43, 1.47, and 1.47 mGy for 2D and 1.92, 1.97, and 1.98 mGy for DBT for the three glandularities. The resultant images were processed to create 2D, DBT planes and synthetic 2D images. Patches of the images with or without a simulated lesion were extracted, and used in a four-alternative forced choice study to measure the threshold diameters for each imaging mode, lesion type, and glandularity. The study was undertaken by six physicists. The threshold diameters of the lesions were 6.2, 4.9, and 6.7mm (masses) and 225, 370, and 399μm, (calcifications) for 2D, DBT, and synthetic 2D, respectively, for a breast glandularity of 18%. The threshold diameter of ill-defined masses is significantly smaller for DBT than for both 2D (p≤0.006) and synthetic 2D (p≤0.012) for all glandularities. Glandularity has a significant effect on the threshold diameter of masses, even for DBT where there is reduced background structure in the images. The calcification threshold diameters for 2D images were significantly smaller than for DBT and synthetic 2D for all glandularities. There were few significant differences for the threshold diameter of calcifications between glandularities, indicating that the background structure has little effect on the detection of calcifications. We measured larger but nonsignificant differences in the threshold diameters for synthetic 2D imaging than for 2D imaging for masses in the 9% (p=0.059) and 18% (p=0.19) glandularities. The threshold diameters for synthetic 2D imaging were larger than for 2D imaging for calcifications (p<0.001) for all glandularities. We have shown that glandularity has only a small effect on the detection of calcifications, but the threshold diameter of masses was significantly larger for higher glandularity for all of the modalities tested. We measured nonsignificantly larger threshold diameters for synthetic 2D imaging than for 2D imaging for masses at the 9% (p=0.059) and 18% (p=0.19) glandularities and significantly larger diameters for calcifications (p<0.001) for all glandularities. The lesions simulated were very subtle and further work is required to examine the clinical effect of not seeing the smallest calcifications in clusters.