Checking, savings, and credit card accounts are all from the same bank. I have everything connected online so I can auto update.

When I enter a transaction, like my credit card payment, in my checking account, it auto populates in my credit card account. Then when I update my CC account, I get a duplicate transaction. But they are both considered downloaded, so it will not let me match them.

Is there another way to handle this, so I don't have to delete duplicate transactions?

Which format do you use when importing transaction? There are inherent problems with QIF import, but the manual gives information on how to avoid them, see bottom of this page. Otherwise, transaction matching is described here.

b.t.w. -- This should work. I use the exact same procedure all the time. I have no problems with it, but I always use .qfx or .ofx import formats.

It is setup to use OFX via the "Update" button, ID as Quicken Windows 2013.

The reason it works for me is that I do not update the CC account over the internet:

- I manually enter a transfer from my checking account to a credit card account on 02/23. It propagates to the latter.
- I download my credit card transactions in ofx format to a local file.
- I import the transactions through the File->Import menu.

The transactions do match.