Last Downloaded Option for reviewing downloaded transactions

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Running latest version of Quicken for Mac and have noticed that when downloading transactions, using the "last downloaded" filter to see the new transactions in updated accounts is not working properly. Been this way for a while. Either you get transactions that you've already seen, or you get no transactions listed even though the account is highlighted as one that has been updated. Only way you can kind of tell what's happening is looking into the register for the updated account and looking at status flags. This feature (last downloaded) had been working great for a long time, but in the last few months not so. Would appreciate any insight. Thanks.