Yes, you can always repeat the action, before the drag & drop too... the matter is:
Many times I get an error when uploading files, or not complete or not the rise, and I have to save the rest, sort, save again, then go up again and would accommodate where it should go.
And, why to re-upload the media, if it is easier to click on "Retry".
Also sometimes that gives errors... the files are upload at original size only, not in large/medium/thumb sizes, so you see the gallery with some pictures at original size. If you see file description, in size sometimes said "0x0", this happened when the host get out of memory for example... Is very unconfortable to use. I really love WordPress, is a very powerful tool, but the main function that I use, the gallery, is really bad (sorry about this, but it's true).
Many thanks for your interest in my idea, if I could help you in something, just tell me.