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I've searched almost all preferences dialog on IntelliJ Idea and haven't found how to undo 'don't ask again action' on the update dialog
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On the main menu, choose Edit | Undo. Press Ctrl+Z .
To navigate backwards, press Ctrl+Alt+Left . To navigate forward, press Ctrl+Alt+Right . To navigate to the last edited location, press Ctrl+Shift+Backspace .
You'll find what you need in the run/debug configuration:
Show dialog: Select this check box if you want to see the Update dialog every time you perform the Update application action.
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