What timeout do you mean? Response timeout is dismissed automatically when the response is received.

Is there a way to have winscp automatically retry if there are timeouts? Also, can the alert dialog be made so that it automatically dismisses itself after a set period of time? It's not all that helpful to start copying a boatload of files, have it timeout (for an as-yet undetermined reason) and then just sit there with that modal dialog on the screen.