A method and system for automatically rotating image files and preventing duplicate uploads in a remote file storage system is described. The system receives an image file. The system calculates a hash value associated with newly uploaded files. The system then automatically rotates the images based on orientation data associated with the files (if included). The system then compares the hash value(s) associated with the new file(s) with the hash values from the existing files stored on the remote file storage system. If the hash values of any of the new files to be uploaded match a hash value on the hash value list, then the system prevents the new files from being uploaded to the remote file storage system.