Sometimes we need to compress a file in order to make it easier to transmit. Sometimes we need to encrypt the contents of a file in order to protect that information from prying eyes. Sometimes we need to apply both compression and encryption to a file. At first, one may think that because these operations are independent of one another that it makes no difference with the order that they are applied to a file.
However, the order in which these operations are applied makes a huge difference. Encryption has the effect of turning data into high-entropy data where entropy is a measure of unpredictability of information content. Therefore the encrypted data appears like a random array of bytes and patterns are far less likely. Compression algorithms work best when there are patterns in the data so that these patterns can be represented with fewer bytes. For example, the LZW (Lempel-Ziv-Welch) compression algorithm builds a dictionary as it compresses data, so when strings of data are repeated they are substituted with an index from the dictionary. When repetition in data is rare, then there are few opportunities for a beneficial substitution to occur. In essence, the entropy of data relates directly to the incompressibility of data.
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