Multiple Image upload issue - skipping images

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When uploading product images via file uploader, it skips images or fails to upload some whether it's 4 or 40 images. There's no notification or acknowledgement that it's been skipped. I just have to find out when I don't see it on the front end. Is this a known issue about uploading images? Is there a way to fix this or avoid it? I do hundreds of images at a time once a month and i am not doing it one by one though I may have to if i can't find a fix. Very time consuming going through each product to see which ones didn't get uploaded.