This is a problem I've had for many months. Have reported several times and still not resolved. Problem is that if you add an attachment and then do something else to the transaction, such as type something into the memo field or mark the transaction as reconciled, the paper clip icon, showing there is an attachment, does not display. To avoid, you have to break the update into two steps, e.g., enter something into memo field, save transaction, then add attachment. To address if you've added the attachment and the icon doesn't display, delete and re-add the attachment. What a pain! And for the problem to have existed for so long. If realize it's not a "Severity 1" problem but come on Quicken, I pay my subscription fee and install updates when available. I'm doing all I can. How about you doing your part???