Embodiments are directed to techniques for simplifying and automating the process of transitioning a storage object to use inline compression either on the same machine or migrated to a new machine. This may be accomplished by determining the raw compressibility of the data of a storage obj ect, estimating the interaction between the compressibility of the data and a structure of the inline compression feature, and automatically performing the upgrade or migration if the expected compression savings exceeds a threshold. Some embodiments further speed the process and decrease the resources by determining the raw compressibility through sampling. Embodiments are directed to a method, apparatus, system, and computer program product for performing these techniques.