a4e743b created the issue

If I log onto an FTP site and drag a file into the window with a name matching the name of an existing file, Cyberduck presents me with the Overwrite Prompt (https://trac.cyberduck.io/wiki/help/en/howto/transfer#OverwritePrompt) to ask me to confirm that I want to do this. This is useful.

If I let the Cyberduck window sit idle long enough for the connection to time out, and then interact with the Cyberduck browser window, it will show me a sheet modal dialog telling me the connection was closed. Clicking on the "Try Again" button will reestablish the connection to the FTP server.

However, if I combine the above two by letting the Cyberduck window sit idle so that the connection closes, and then drag a file into the window with a name matching an existing file, I get the "Reconnect" dialog with the "Try Again" button, but clicking on that, the file or files are uploaded with no Overwrite Prompt.