A prediction is computed from an input data, at a time, that a user will need to use a set of files during a future period. From the set of files, a subset of those files is selected that are designated for synchronization with a remote storage over a data network. A priority of the file is computed according to a characteristic of each file. A synchronization operation is caused to occur, to synchronize the subset of files in an order of priorities associated with the files in the subset.