The present disclosure relates to systems, non-transitory computer-readable media, and methods for predicting and prefetching relevant thumbnails from remote servers to client devices based on a dynamic determination of file display criteria. For example, a thumbnail prefetching system utilizes previous thumbnail requests to predict a file directory sort order and determine thumbnails the operating system at the client device will next request. The thumbnail prefetching system can then prefetch the thumbnails prior to the operating system at the client device making thumbnail requests for the files. Thus, when the operating system does request thumbnails for the pertinent files, the thumbnail prefetching system can provide the thumbnails efficiently and quickly while leaving thumbnails for other (unrequested) files stored at the remote server (and not downloaded to the client device).