At that point, you either A.) Lose the code that it supplies you with or B.) think it didn't work.
And so then you try to upload the image again, and you get this error:

What gives?
What gives is that a file by that name already resides in the directory for your blog, and MT won't allow you to overwrite it. Any attempt to upload a file by the same name will not work. (Note: Aside from our hypotheticals listed above, this can frequently happen when you're uploading a file with an exceedingly common name ... for example, "Cowboys.jpg" or something like that.)
Now, adopting a naming convention that makes each image more or less unique will help minimize these conflicts. I usually throw the date in front of every image/item I upload ... 041708_cowboys.jpg, or something like that. (It also helps when we're trying to track down an item in a large directory.)
In the short term, try re-naming the file ... Cowboys2.jpg or, better yet, 041708_cowboys2.jpg ... and then upload it as usual.
And, as always, contact us if this doesn't work.
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