According to various aspects and examples described herein, systems and methods for uploading/transferring files are provided. In one aspect, an upload manager is provided, the upload manager for coordinating a transfer of an image file to a remote location. In one example, the upload manger includes logic for creating a reduced size image file associated with the image file, the reduced size image file having a smaller data size than the image file, initiating a transfer of the reduced size image file to the remote location, and initiating a transfer of the image file to the remote location subsequent to initiating the transfer of the reduced size image file. Transferring a reduced size image file (e.g., a thumbnailed version) may allow for relatively fast transfer and access times of the reduced size file compared to the full size version image file.