Ok, I will try that next time. I actually just did it the way I normally did and then came back in here to see if anyone replied, so I saw these after I was done for today :)
I have noticed that if I have an entry that I create, the left hand column shows that same dollar amount in Green instead of Red when I load my transactions. If I delete my manual entry, the one on the left turns red again. So, it seems that it is recognizing similar dollar amounts, but did not show as reconciled (with a Check Mark) on the calendar unless I dragged it over.
As I look at it more, it is starting to make sense and I see how it is working, but I will try to drag one from the left onto the existing entry and see what it does.
Thanks again! Love this app!