"Matching" transaction no longer match existing entries

@Quicken Kristina To add some more detail, the problem @Axe21 described below about having to manually delete after matching does NOT happen to me. If I "match to a downloaded transaction" on the unmatched entered one, the downloaded (and "matched") one goes away. This issue only exists (for me) for register entries from the re-occuring bills (or things with reminders), not one off entries that I put in registers.

Attached is a pic from today of how it went down.

I see that a seemingly duplicate issue managed by @Quicken Anja is currently open.

I have done the "report a problem to quicken" thing.

For kicks & giggles, I decided to go through each of my banking/credit institutions and reauthorize each login & OSU download permissions.

Quicken finally changed the date for "last download March 4" to "last download April 18" but that's the only improvement I observed. (I've downloaded transactions every few days from March 4 to April 18 and in most cases, downloaded the same transactions each & every time since March 4.) In other words, it's still broken.

Tonight's OSU downloaded most, if not all, of my transactions across all banks for the last 1.5 months. AGAIN. As well as some Target credit card transactions that were over 6 months old, already recorded, cleared & reconciled. OSU deleted the transactions already in placed, redownloaded them and marked them "new".

Submitted logs for multiple accounts.

Same problem for me for the last month or so. Now running Quicken Classic Deluxe, R67.7/Build 27.1.67.7. It happens with expense entries posted from Bill and Income Reminders. Update is run, transactions are downloaded and shown as matched, but when accepted they create a new entry without an expense category. To fix this I mark the original transaction as cleared and delete the new entry. This happens with Chase, Citibank and Amex credit cards as well as UMB Bank.

I have been seeing the same issue on my Quicken. This is happening for weeks including the new version 27.1.67.7. It is very annoying and looking forward to this being fixed.

This morning I did the OSU and the bills entered from the stack view / calendar were properly matched with downloaded transactions. This was CapitalOne where it worked. I can't say it worked as I wasn't looking for it to work, but noticed that the transactions were matched. I'll keep an eye on it for future OSUs.

@Quicken Alyssa Well, this morning back to the usual in my Schwab Checking. Unsure if last time was a fluke or the account, but this morning downloaded a transaction and didn't automatically match to my already-in-register-from-calendar transaction.