A method of smart path finding for a file operation is disclosed. A data structure is provided to store reference points, file paths and use counts. Each of the reference points is a URL or an email ID and is associated with at least one of the file paths. Each of the use counts is tied to one of the file paths. The data structure is searched when a reference point is hit for downloading, uploading, attaching or detaching a file. When the reference point is found to be or to be similar to one of the reference points, one or more file paths associated with the one of the reference points are ordered, by one or more use counts tied to the one or more file paths, to form a list including one or more suggested file paths for downloading, uploading, attaching or detaching the file.