Organize Uploads Into Month and Year Based Folders Not Working

I’ve enabled the “Organize my uploads into month- and year-based folders” setting for uploading Media, however when I upload a PDF file when modifying a page the directory is wrong. The way I understand it, the year and month values in the path should change based on the file or upload date. Well, I’m uploading a file and it is April 2009 and the path is 2008/12. Anyone know what I might try to figure this out? I changed the permissions on the wp-content and uploads directories as indicated in the Codex, but still no dice.