Many advanced dimensional measurements exist that incorporate two-dimensional images of the object to be measured, such as structured-light measurements and photogrammetry. The measurements are quite complex and often suitable calibration artifacts are not available; consequently, a traceable uncertainty analysis is difficult. Advanced optical simulation packages can be used to assess important aspects of the uncertainty. These packages can simulate a virtual object to be measured, simulate a virtual camera, and trace rays as they leave a light source, scatter from the object, propagate through the camera, and arrive at the camera image plane. The result is a virtual image of the object whose dimensions are known. The virtual image(s) can then be processed as part of a dimensional measurement and the results compared to the known dimensions of the object. This allows different uncertainty aspects to be isolated and explored. It can be used to validate and understand the current methods of estimating measurement uncertainty, explore optimal measurement conditions, and/or test data analysis algorithms. These types of measurements involve a camera calibration process and the technique can also be used to check this step. This paper demonstrates the approach as applied to a photogrammetry measurement of a box.