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Abstract The properties of clouds that may be observed by satellite instruments, such as optical thickness and cloud-top pressure, are only loosely related to the way clouds are represented in models of the atmosphere. One way to bridge this gap is through “instrument simulators,” diagnostic tools that map the model representation to synthetic observations so that differences can be interpreted as model error. But simulators may themselves be restricted by limited information or by internal assumptions. This paper considers the extent to which instrument simulators are able to capture essential differences between the Moderate Resolution Imaging Spectroradiometer (MODIS) and the International Satellite Cloud Climatology Project (ISCCP), two similar but independent estimates of cloud properties. The authors review the measurements and algorithms underlying these two cloud climatologies, introduce a MODIS simulator, and detail datasets developed for comparison with global models using ISCCP and MODIS simulators. In nature MODIS observes less midlevel cloudiness than ISCCP, consistent with the different methods used to determine cloud-top pressure; aspects of this difference are reproduced by the simulators. Differences in observed distributions of optical thickness, however, are not captured. The largest differences can be traced to different approaches to partly cloudy pixels, which MODIS excludes and ISCCP treats as homogeneous. These cover roughly 15% of the planet and account for most of the optically thinnest clouds. Instrument simulators cannot reproduce these differences because there is no way to synthesize partly cloudy pixels. Nonetheless, MODIS and ISCCP observations are consistent for all but the optically thinnest clouds, and models can be robustly evaluated using instrument simulators by integrating over the robust subset of observations.