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Why don't downloaded transactions match the ones already in the register?

There's a sudden change in Quicken's behavior. I'm accustomed to entering transactions in the register from receipts, etc. and then downloading all accounts, and watching as the "New Match" messages appear. Today, suddenly, Quicken is ignoring the item already in the register, entering a new, identical transaction, marking it "New Match" and placing a "C" in the CLR column. The original entries I had made are marked "Uncleared." This happened on numerous items and I know they were correctly entered as to Payee and Amount. [Quicken Premier, Windows 10, user for more than 20 years]
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Answers
Note this was in a Direct Connect account, it might vary for an Express Web Connect account.
I picked out two transactions from my current data file one for 20.38 on 11/18/2020 and one for 13.77 on 11/19/2020.
I purposely put in the first one with 11/17/2020 (a day before the transaction) and the second one for 11/23/2020 (a day into the future).
Before updating:
After updating:
Even though I didn't get the duplicates you mention, I also didn't get the New Match for these transactions, and certainly should have. This is a change and a bug.
Note I did try one more thing and that was entering a transaction with a future date (from today not from when the transaction actually came in) and that one wasn't matched and it was duplicated, but that was "expected".
Windows 10 Pro 32 & 64-Bit Build 21322.1000
also Windows 10 Pro 64-Bit Build 19042.804
Note: Product What's New in Quicken is grayed out.. Also Year is stuck on 2020 and Copyright Date is stuck 2018 in About Quicken.
View: https://community.quicken.com/discussion/7859218/work-with-copies-of-your-actual-quicken-data-files/p1?new=1
And even though I can appreciate the fact that one way to workaround this problem might be to turn off automatic entry mode, by no means should that be the "fix". Automatic entry mode should work properly, and it currently doesn't even in my testing (no New Match status).
Note I have seen the no New Match status bug happen when using sync to Mobile/Web, but I didn't have that on in this case. But you might and it can contribute to such problems, so please state if you are using Mobile/Web sync.
Everything has worked without issue until I opened Quicken yesterday and it downloaded updates.
The online account shown in the clip is Capital One, with Express Web Connect +, but it also affects two Bank of America cards with Express Web Connect.
I've just turned off Mobile & Web Sync and will see if this makes a difference.
I'm running Quicken Premier, R 30.10, Build 27.1.30.10; on Windows 10, Home, 64 bit, Version 2004, build 19041.630.
Thanks, all
https://community.quicken.com/discussion/7882641/qcs-express-web-connect-is-cloud-sync
At this point my suggestion would be to contact Quicken Support and see if they have any suggestions.
Contact Quicken Support