A file operations engine is provided that manages many user interactions with their files via a computer system. The operation engine may provide a user with the option to keep both files that have a file name conflict. It may further permit the user to rename a file involved with a file name conflict. The operations engine may also automatically rename one of the files of a file name conflict by appending a character to a root of the filename. The character may include the lowest integer available for the root in a destination for the files. The operations engine may provide the option to keep both files as part of a pre-calculation of potential errors for a requested operation. The operations engine may place file name conflicts in an error queue and permit the user to select an option to keep both files after the conflict is encountered.