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Rotating a raster that is projected on the fly causes the image to disappear.
This is a known issue that deals with a 'double transformation' applied to a raster. The first transformation occurs when the raster is projected on the fly because it is not in the same coordinate system as the data frame. The second transformation occurs when the raster is rotated. Currently, ArcGIS does not support the double transformation.
To display the raster with a rotation, the raster needs to be projected in the same coordinate system as the data frame. To do this, follow the steps below: