At least on Windows 7 it looks like opening a native file dialog with FileChooser from within a component in a Calloutbox causes the Calloutbox to be destroyed. Using the FileChooser with the JUCE file dialog seems to avert this. Is this the intended behavior? On macOS (El Capitan) this doesn’t happen.
I’ve just pushed a fix for this to the develop branch. The native Windows file dialog should now have the same behaviour as the JUCE and macOS file dialogs when opened from a CallOutBox.
Thanks! Perhaps not suitable to report here, but I noticed that on macOS the same problem exists when using the JUCE file dialog from within a Calloutbox. Opening the JUCE file dialog causes the Calloutbox to disappear/be destroyed when the file dialog is closed.