It's frustrating you can't select multiple files when clicking Insert Image > Upload Image > click here. Why doesn't this dialog allow selecting multiple files like the Attach files dialog? This would make clicking Insert image > Upload Image and selecting multiple files functionally identical as clicking Attach files then click Insert all with the benefit that a) it's functionally more intuitive to click Insert Image when inserting an image than to click Attach file then click Insert and b) it would simplify the existing two step process to click Attach file then Insert or n-step if clicking Insert image once per n images.
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