Why are my downloaded transactions not matching correctly to those entered in Quicken?

Question

When I download transactions from my bank there is a list of transactions that match what is currently in my Quicken register.  I do not automatically have Quicken accept these transactions and reconcile my account.  I manually accept each transaction.  When I click on a transaction that has a match, it highlights the wrong item that Quicken has matched it with in my register.  Then, I have to go in and manually match with the correct transaction, or as is the case many times, there is no correct transaction that matches in my register and I have to manually add the new transaction (that Quicken said it had a match for but didn't) and then manually match the transaction I just entered and accept it.  Any idea how to fix this?

Chris_QPW · Answer

This answer shows the lack of knowing how this feature works.  @mark1kim1 description is clearly the workflow when "Automatically add to banking registers" is off.

With "Automatically add to banking registers" on the flow is like this.

Each transaction match is marked with a status of "New Match".
If the user feels that match is wrong, they click on the New Match status and select to unmatch it.
Next, they have to click on the manually entered transactions "Uncleared" status and select the Manual Match option.  This will bring up a dialog of all the matching downloaded transactions that have the same amount as the manually entered transaction and have not yet been matched to a manually entered transaction.

The list of transaction to match to that exists when not using this feature doesn't exist!

In summary in "automatic mode" you are manually matching from the manually entered transaction to the downloaded one.  In "non automatic mode" you are matching from the downloaded one to a list of possible manually entered transactions.

What's more in "automatic mode" the match has to be the exact amount.  In the "non automatic mode" the list of possible matches is any manually entered transactions that have yet to be matched to a downloaded transaction.  This of course leads to a very long list if the person doesn't do everything perfectly right and get all the manually entered transactions properly matched.

The current one saving grace is something that @Damian mentioned.  A few years ago, they put in some kind of limit for the list.  I think it is like 30 or 60 days.  As in manually entered transactions are dropped from the list after that amount of time.  It used to be that one could get matches that were decades old for a transaction that was just downloaded.

Also, let me say that other than the cutoff I just mentioned Quicken doesn't use the downloaded date to determine which transaction to match to.  Instead, it just picks the first one in its list.  So, if you have two manually entered transactions for the same amount, Quicken is always going to pick the oldest one first.

EDIT from what I can tell the actual automatic matching algorithm for both "Automatically add to banking registers" mode on and off is the same.  Also, at one point I tested the cutoff date for being on the list pretty extensively and I do believe it is 30 days, but it has been at least a year since I did that, so my memory might be a bit fuzzy on the exact number of days.  I personally use the "Automatically add to banking registers" mode so I don't test this on a regular basis.

[Deleted User] · Answer

@mark1kim1 - The easiest thing to start with is to keep unmatching and matching transactions.  Sometimes things will just correctly realign themselves.  If the issue persists, and you haven't already, try these troubleshooting tips -

https://www.quicken.com/support/advanced-data-file-troubleshooting-correct-problems-quicken-windows

The other thing to first check what type of connection you have set up in Quicken with your bank.  You can check what you have set up by going into the Online Services tab in Account Details.  Express Web Connect (EWC) can be problematic.  Direct Connect (DC) is the better method but most banks charge a monthly fee to use it.  If you bank offers it and there is no charge, I would update your connection to Direct Connect.

Otherwise, you can deactivate and reactivate online services for this account.  If you do this, you should deactivate and activate ALL your accounts that you have with the bank.  If you do it with just this one account, it will cause further issues.

https://www.quicken.com/support/deactivate-and-reactivate-online-banking-services-quicken-account

GeoffG · Answer

Make sure the following setting is unchecked.

This allows you to match/accept transactions. With this checked, you are allowing Quicken to run on auto-pilot, not a good option.