Chase Import - missing transactions, very out of date charges

What I would do is first check to see if the charges are in the QFX file.
It is a text file.  I might be a bit hard to read, but you can search for the missing payment payee names (or maybe another payee just before it and get to the right section and I think you can figure out if the charge is in there or not.

From there we should be able to know if this is a Chase or a Quicken problem.

EDIT:  As far as knowing if your records are correct or not, that is what doing a proper reconcile can determine.  Reconciling is the process of checking to make sure your Quicken register and your financial institution's records are the same.

Oh, I didn't know that you were using the QFX file in YNAB, if that was the case, then yes it does sound like there was some problem with Quicken not importing it correctly (provided there isn't some kind of syntax error in it that YNAB ignored).

Well, I don't see anything wrong with that transaction, Quicken should have imported it.

When you say "auto reconciliation" are you talking about the automatic reconciling after a download?
There are some confusing terms here.

There is reconciling to the "statement balance" (which could actually be a balance one looks up on the financial institution's website). You get a dialog for the ending balance, and then the reconcile dialog.
There is reconciling to the online balance.  You get the same dialogs, but select online balance.
There is reconciling to the online balance and not ask if you want to do it differently.  You don't get the first dialog, but you get the reconcile dialog.
There is automatic reconciling to the online balance after downloading transactions, and if the reconcile balances, don't even show the user the reconcile dialog.

First dialog:

Reconcile dialog:


As you can see "uncleared" aren't "missing", they aren't included in the balance, but the assumption here is that if the Statement ending balance is correct and any of the "uncleared" transactions should be in it, then then you would have a difference until you selected them (which marks them cleared).

Note Quicken has two modes for importing transactions, one is automatic transaction entry mode, and the other goes through a Downloaded Transactions tab.  Here is with that the automatic transaction entry mode on for banking accounts.


In this mode you should never use automatic reconcile.


The reason is because you need to review the downloaded transactions to make sure that the categories and payees are all correct.  When you download in this mode the status of these transactions will be New or New Match, and you can click on the status to mark it reviewed.

Reconcile on the other hand only looks at the amounts, but it will clear these status indications if it balances.

If you have the Automatically add to banking registers mode off, then the transactions go into a Downloaded transactions tab at the bottom of the register, and you accept them one at a time into the register.  As such you are reviewing the categories and payees as you do that.  And once that is done is when the automatic categorization kicks in.

One last thing to mention.  The ending statement date used determines what uncleared and cleared transactions are included in the reconcile (their posting date has to be on or before the statement ending date).  But even future dated reconciled transactions are included in the Cleared balance calculation.  For this reason, you can't reconcile past intervals if you have already reconciled a newer time frame.

You have to always reconcile from the past to the present.