@rawpwr101 

"I'm not understanding where in QB its going wrong because if its reconciled in a prior month, why would it still be showing up as an outstanding item?"

Everything you're describing sounds like the transaction on the reconcile screen is a duplicate transaction.  It's my experience that if you undo a matched transaction, and then attempt to match it again, QB only gives you the option to "Add" the unmatched transaction, not match it.  Then, when you click "Add", that creates a duplicate transaction.

You probably know this but, to confirm whether or not it's a duplicate transaction, click the magnifying glass in the upper-right and type the amount in the search box.  Double-check by going to your bank register and organizing the payment/deposit columns by amount and find the transaction(s).