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(40 total votes)
You can do this by uploading the other picture and then reporting that as a duplicate of the one your are trying to replace. The staff will then take a look.
If we just let users do this at will, it could lead to abuse, like they get a particular picture onto the front page high score section and then they can replace it with whatever they want.
I think that it would be a useful feature to have. Say for instance, if after uploading an image, that you notice it's a duplicate or if for some reason you change your mind (or discover later it doesn't meet the upload standards) that you want to substitute that upload with another upload instead of deleting it outright. You could have the delete upload option AND a substitution option.
Could add a time-limit to substitute an existing image, say maybe a few hours or even a day?
Of course, I'd like to air this idea and see if it's a popular one in our online community.