Post Image Plugin single.php weirdness

Alright, great plugin I love it https://guff.szub.net/2006/02/09/post-image/ Figured I would post here, as I can’t find a thread here.

You can see it in use on the sidebar of https://tradebur.com (the three thumbnails associated with the 3 posts automatically)

When you click any post to go to the single.php, which uses the same sidebar, the images do not appear. Or only one image appears if you are currently viewing that post. I have no idea why they aren’t displaying on the single.php.

Any ideas would be helpful, I’m getting nowhere fast. Thanks.