Embodiments of the present invention provide a solution to optimize data transfer between a mobile device and a cloud storage provider. Specifically, embodiments of the present invention may select one or more files for transfer from the mobile device to a cloud storage device based on an analysis of a set (at least one) of factors such as: (1) the percentage of local storage being consumed on the mobile device; (2) the mobile device's billing plan, and whether file transfer will cause the billing plan to be exceeded; (3) a capacity of a link between the mobile device and the cloud storage provider; (4) dates of last access for files stored on the mobile device; and/or (5) a battery power remaining in the mobile device (if applicable). Any files selected based on an analysis of these factors can be transferred via the link and deleted from the mobile device. Typically, a file is a candidate for transfer if it has not been accessed recently (e.g., within a certain time period), the link and billing plan can accommodate the transfer of the file (e.g., determined based on the size of the file), and there is sufficient power to make the file transfer.