Sorry if I'm using incorrect terms here. What's going on is, when I edit any content, as the the types of content under 'Content Management > Content Type', there's the Image: field, which I think is provided by the CCK Imagefield module or Imagecache. (I'm on 6.x-3.10 of Imagefield)
When I choose a file and click upload, I get a thumbnail image (http:/mysite.com/sites/mysite.com/files/imagefield_thumbs/image.jpg?1357151034). When I click 'Preview', I get a preview with the image I uploaded (http://mysite.com/sites/mysite.com/files/imagecache/product/image.jpg). When I save, the image is gone, and going back to the edit form, it doesn't show up as an attached image. One possible clue; this content type isn't 'product', but it's in sites/mysite.com/files/imagecache/product/.
This all worked until a couple of weeks ago, when I updated a bunch of modules. I did a whole site backup before I ran the updates, and a development version of the site on my local computer doesn't have this problem on up to date modules. The only way I can replicate it on my local machine is to use a backup of the database from after this error occurred.