A folder or file on the first computing device to be synchronized with a second, portable computing device is selected by a first icon corresponding to the folder or file being dragged and dropped to overlap with a second icon corresponding to data management software running on the first computing device. Both the first icon and the second icon are displayed on the user interface provided by the data management software. A folder or file on the second computing device to be synchronized with the first computing device is located at a predetermined location in the second computing device for synchronization with the first computing device. The selected folder or file is partitioned into a plurality of segments. The synchronization of the selected folder or file is performed in terms of these segments while maintaining a count of the number of segments that were synchronized.