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There does seem to be some problems with the way MD matches, and records matches to, downloaded transactions.

I had not seen the matching problems others have reported until just the last few direct connect downloads I did of my Discover card. Now, I see the opposite of what you report in that I get duplicate register entries if I click record and do not notice it is already in the register, but not matched by MD, and, if I delete the downloaded one (in favor of one already in the register), MD will show it over and over after downloading as a new transaction. The workaround is to delete the transaction already in the register and then do a "record". However, the matching algorithm should be good enough that you can record/match an already entered transaction without problems.

I extracted -using MD's extract command - the financial file; I then downloaded all of the transactions - using the financial institution's download facilities - that MD refused to download and extracted the FITID's ; I then compared those FITID's and there were NO duplicates.

I checked the FITID's of ALL of the records in the moneydance file against ALL of the transactions that needed to be downloaded -- and there were no duplicates

The question that needs to be answered is "HOW does moneydance determine what it is going to download"?

I agree. The method it uses seems to not work real well.

My post was meant to point out another way in which the method does not seem to work well, even if it can be worked around in the way I mentioned.

My workaround works for the problem I described, i.e. duplicate entries.

I have not had the problem you described. I only posted mine because it could be related and, as such, the post might add some impetus for getting both resolved by the developers.