This is driving me crazy and I know others are having the same issue from the posts, but I haven't seen anyone resolve it. This started happening right after Quicken switched to the non-PDF attachment format. Yes, the attachment icon register column is checked and shows right under the date field. Sometimes the paperclips do appear in the attachment column after making attachments. But other times when you make an attachment and save it the paper clip icon does not appear. If you attach it again, then it does appear. Today for the first time I had to attach an attachment 3 times before it appeared. I have reported this problem through the help menu several times but it still keeps happening after several Quicken updates. Please fix this!!.