Systems and methods for iterative near lossless image compression are provided. An exemplary computer-implemented method of compressing image data can include performing a plurality of compression iterations. Each compression iteration can include at least one decision regarding a loss of image data. The method can also include updating an entropy model following each compression iteration. The entropy model can describe an entropy associated with selected of a plurality of data blocks. The at least one decision regarding the loss of image data can be decided, for each compression iteration, based on the entropy model as updated following the previous compression iteration. Further, a total loss of image data from each data block can remain within an acceptable loss bound associated with the pixel described by such data block. An exemplary system can include a loss determination module, an entropy modeling module, a compression module, and an entropy coding module.