Lots of posts on this one. None that I saw mentioned this simple fix so thought I'd add it.
I'm using Windows 10
I found if you add via drag and drop or browse your receipts YOU HAVE TO HIT ENTER right after adding it to your line item. Quicken will then move down one line so you need to go back if you stlll need to edit anything else. Doing that has made ever paperclip icon stick and stay visible !!
Side note: If you save your receipts with $10.99, for example at the head of the name, and a date at the end of the name, it's easy to search for them when polishing up your quicken file especially if you start with a directory for that year like Tax Receipts 2023.
