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One is a screenshot (2,7MB) and the other could be a bit too big but was accepted the first time i uploaded it, can't see it cause of the problem where images wont upload until the second try (the why to that question was answered already), so I dont see why those would cause any issue, but again.
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2.7MB sounds way too large, I think I even had something rejected before for being around 500kb
When you're trying to reupload the image, are you just saving it as the same filename? If so, iClassic may be caching the old image so you could try renaming the file to a name you haven't tried uploading before