joebastone

I’m running into this problem as well, and seem to have stumbled through a workaround. For reference, I’m using 2.8.1.

1. Add new post.
2. Manually type in [gallery] into post form.
3. Save draft.
4. Upload pictures.
5. Save all changes.
6. Now you should see the option to insert the gallery into the post.
7. Insert into post.
8. Delete the second [gallery] that appears in the post form.

It’s a pretty condensed list, but I think you get the idea that using the [gallery] shortcode seems to convince WP that you really want to attach the images to the post.