Thank you for reaching out to the Community and telling us about your issue, though I apologize that you are experiencing this. Can you please provide me with some more information about this issue?
Is the issue biller specific? Does this only happen with some billers and others behave as expected? Also, have you tried deleting and re-adding the bills/billers that are having issues?
Quicken Alyssa
briankennedy said: So if you look at the screenshots I have attached. The screenshot "overdue.png" shows that I have 4 bills currently overdue under "Bills & Income" -> "Bills" tab. If I then go to "Bills & Income" -> "Activity" tab which is represented in "paid.png", the activity for at least two of them on the overdue list are marked as paid. If I then go to the Register from the account in which I paid those bills and download latest transactions, I see the two bills in there with the amount I paid on those dates.