Oooo ... I had not noticed that. Hmmm ...
It's set to always be on top ... but since there are several windows on the desktop, all set to be on top ... the logic gets screwed somehow.
Not sure if it matters that this is launched from a plugin too?
I notice that the dialog will end up on top of the main plugin window, but not any other secondary plugin windows that also happen to be "always on top".
Anyway, no big deal, I have some custom windows for this sort of thing that I can explicitly bring to front, which seems to work fine.
Hmmm ... Also, I would upload an image, but it keeps telling me it can't upload (it is less than 1 MB). So .... not sure what's going on there either.
I also see you are using ckeditor now, with the imagegallery plugin. You may want to disable that in the user view though (since it cleary doesn't point to a public directory, and I doubt you want to use that anyway).
Great to see all the amazing changes with Juce lately!