If you don’t know what SharePoint Designer is, look it up. Its a great tool, but dangerous (at least the 2007 version)! I have a big list of attachments from items that cease to exist due to the expiry policy. The attachments just sit in there never used. As you can probably tell, we are way out of date on our servicepacks and updates, as orphaned attachments due to expiry policys got fixed in a 2009 update ( -3rd bullet). Well time to charge my lasers! I decided to use SharePoint Designer to my advantage.
From the beginning of the project SharePoint Designer 2007 refuses to delete any attachments from a List from the position they are at now. So I tried some tests and tried to work around it. I found an impractical but legal solution.
You can usually assume an older folder by going to the List and hovering over the attachment to see what folder number the oldest post is on(site/Lists/ListName/Attachments/453). That will determine the number of attachments you need to delete (Folder #’s 1-452 in this case)! Happy SharePointing!