I have two identical credit card transactions on the same day from a Express Web Connect+ account . If they post and download on the same day, they usually match backwords in that the first transaction matches to the second and visa versa. This isn't a problem in that case since they look identical. However, if there is a one or more day delay in one transaction posting, the second transaction never presents a match. I think it's because the downloaded second transaction thinks the first was already cleared and never gives a choice to match to the second uncleared transaction. It would be nice if there was some message or choice given but there isn't. I know I can manually play games to get the right match or force a match on the second by setting the cleared bit but this seems like something that Quicken could easily facilitate. Any thoughts?