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I added calls to QApplication.processEvents() either side of the various actions on the progress object, and then everything worked as expected including all messages displaying correctly, and the dialog hiding itself at the end.
I almost certainly have far more calls than I need, so I will start removing them gradually to see what the minimum set is to get correct behavior, and then let you have the patch when I get to the minimum set. That should be easier in the short term than worrying about any refactoring.
I wonder why it works OK on your machine and not mine? Perhaps you have a faster machine or a multi-core processor so that changes the event handling timing significantly?
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