A file operations engine is provided that manages many user interactions with their files via a computer system. The operation engine may place certain classes of errors in an error queue while performing a requested operation without waiting for a user to satisfy the errors prior to continuing with the operation. In addition, the operations engine may pre-calculate potential errors for a requested operation prior to performing the operation. Dialogs may be provided to a user to satisfy errors listed in an error queue and/or identified while pre-calculating potential errors. Methods are provided for handling file operations errors and for interacting with a user interface for file operations. Computer-executable instructions for implementing the disclosed methods are stored on computer-readable media.