My impression is that you're being too passive here, somehow assuming despite the evidence that all you need do is "push a button" and that the accounting for your complex transactions will somehow be laid before you. You're spending more time and effort trying to download and then attempting to fix things after the fact than if you'd simply entered the transactions manually to begin with.Since you've just started over with a new file you might want to start over again. This time specify that transactions NOT BE automatically entered in the Quicken Accounts. Enter manually enough history to get your current positions established, and then do your downloads. Then go through the downloads one at a time either accepting matches, deleting them, or matching them manually to already entered transactions, and never accepting placeholders. A placeholder is prima facie evidence that something's wrong and it's simply easier to deal with them when they're staring you in the face and not buried in a bunch of already entered transactions, some of which, if transactions are entered automatically, have wrong dates/amounts/descriptions.It sounds like you could be the victim of bad downloads here and the fault could be attributed to either the broker or Quicken here, depending on how that information is being obtained. It may be possible to sort that out; what broker are you using and what connection type is being employed? (https://www.quicken.com/support/how-quicken-connects-your-bank)