Online bill pay check number changed to "Paid"

Question

For the past couple of months, one of my recurring scheduled online bill payment transactions (set up for the 1st of every month) in my checking account register has had "Send", replaced by "Paid", and marked as cleared. When I show the details in the register, it shows it was matched to a different transaction on a much earlier date, with a different name, but the same $ amount, and that transaction - which was valid - no longer appears in my register.

I've been a Quicken user for over 20 years and have always trusted it. I can understand something being mismatched as CLR in the register occasionally, but this is a pretty serious issue! How does a transaction that is scheduled in the future get matched to a transaction from the past?

Has anyone else experienced this?

UPDATE:

Clarifications to my initial message and:

After googling and spending the past 3 hours or so making calls to the bank and the recipients, I was able to resolve this by unchecking the setting "Automatically improve the quality of downloaded payee names and categories" under Connected Services. Once I unchecked it, my missing transaction reappeared and the online bill payment transaction was correctly marked "Send".

Hey Quicken, how does a serious issue like this get past QA?

Don Arnel · Answer

That makes no sense. Why would a downloaded transaction be matched to a bill pay transaction that had not been sent yet (i.e. no check number had been assigned yet)?

Also, Quicken won't let you send bill payments on weekends or holidays. It forces you to manually change the date.

Don Arnel · Answer

Not sure you saw my updated message since I clarified a few things. The downloaded transaction was matched to a online bill payment transaction scheduled for Aug 1st.

It's also possible that the missing transaction came back due to me rejecting the automatic match at some point in my frustration. I may have just noticed it after unchecking the other setting.

It's still a pretty serious issue considering the downloaded transaction was matched to a future scheduled bill pay transaction. If I hadn't noticed that Send was changed to Paid, I assume the payment would not have gone out.