I've been having this problem for years (probably 5-8+ years). Every week I perform a 1-step update to update quotes and download transactions. But I only accept transactions one a month (when I reconcile against statement). So there are often unaccepted transactions in the "Downloaded Transactions" pane.
New transactions don't show up in the list unless I exit Quicken and restart. For example, I had 3 transactions in the list as of last night (12/15, 12/19, and 12/20). I performed OSU today and afterwards still had the same 3 transactions in the list. I knew dividends were paid out this week so I restarted Quicken. Sure enough, the "Downloaded Transaction" pane now shows 7 transactions (four new ones from 12/27).
This happens in all my investing accounts - it is not limited to a specific financial institution.
