Aggressive resolution enhancement techniques such as inverse lithography (ILT) often lead to complex, non-rectilinear mask shapes which make mask writing extremely slow and expensive. To reduce shot count of complex mask shapes, mask writers allow overlapping shots, due to which the problem of fracturing mask shapes with minimum shot count is NP-hard. The need to correct for e-beam proximity effect makes mask fracturing even more challenging. Although a number of fracturing heuristics have been proposed, there has been no systematic study to analyze the quality of their solutions. In this work, we propose a new method to generate benchmarks with known optimal solutions that can be used to evaluate the suboptimality of mask fracturing heuristics. We also propose a method to generate tight upper and lower bounds for actual ILT mask shapes by formulating mask fracturing as an integer linear program and solving it using branch and price. Our results show that a state-of-the-art prototype [version of] capability within a commercial EDA tool for e-beam mask shot decomposition can be suboptimal by as much as 3.7× for generated benchmarks, and by as much as 3.6× for actual ILT shapes.