Flour milling separates endosperm from bran through repeated roller milling and sifting, in which the size distribution of particles produced by the initial breakage of the wheat kernels critically affects the process. The double normalized Kumaraswamy breakage function (DNKBF), previously developed to describe wheat breakage during roller milling, was extended to refine the modeling of the effect of roll gap on breakage. The DNKBF describes two populations of particles arising from roller milling of wheat, a narrow peak of mid-sized particles and a wider distribution of both small and very large particles. A new dataset was obtained from milling a set of wheat samples bred to give a range of shapes by cross-breeding a conventional wheat, Cappelle, with an almost spherical wheat, Triticum sphaerococcum. A residual analysis showed a statistically significant effect of kernel shape on breakage using this new dataset. This analysis supports earlier suggestions that more elongated kernels break to give slightly larger particles than more spherical kernels of equivalent hardness, because of the relatively greater bran content of elongated kernels. The extended DNKBF was also used to model effects of moisture content, showing a distinct disjunction at around 16% moisture that aligns with commercial practice for wheat milling.