sounds like your images are getting cached by the browser.
a cheap hack/workaround is do something like:
<img src="whatever.png?<?php echo time(); ?>" />
to my knowledge that doesn't confuse any browsers
the only downside (and this is just my personal feeling) is that it creates a new cache entry in your temporary internet files every time you view the image (the timestamp at the end of the src="" attribute pretty much guarantees that it is always unique ... even if the image itself hasn't changed)