Jon said: I think a couple of changes to Quicken would help address this. First, tell the user when there's an error requiring a placeholder fix, so at least they have an idea something is wrong. In my experience, the placeholder transaction is frequently not the correct fix (as in this case) and the user has to do some work to figure out what's really wrong. Second, instead of backdating the placeholder transaction to the beginning of the account, backdate it to the most recently reconciled transaction - make the assumption that everything was correct up to that point. That puts the placeholder transaction where the user is likely to see it & in the range of dates where they are going to be looking for a problem.