In the admin bar, the "Add New" button links to the media library instead of the upload page. This means when one clicks the link, they must then hit "Add New" on that page to upload. This is an annoying bug, it should be fixed.
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Bug Report: "Add New" in admin bar won't add media
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This has pretty much been how it's always worked. The purpose of that part of the admin bar has really been to just direct you to the correct section, but I'll pass this on to our developers as a feature suggestion.
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OK, it would really make more sense to link directly to the upload page.
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