Hi Adrian_A

Hope you are well. 

I am new to QBO and having trouble with something along the same lines. I have a supplier I get materials from and get billed monthly. When I pick up materials I receive a receipt for the amount that will be billed to my account. I upload that receipt to QBO "Plus" and create a bill. At the end of the month I uploaded the statement ($818.75) and categorize as an expense (it is unmatched waiting for a matched credit card transaction) . When I select the month end transaction in expenses it shows up with all the corresponding bills on the right side with an "ADD" option. I add the bills to equal the amount of the Expense (Which has now turned to bill payment).

I fill in "amount" box to equal the total of the bills for the month ($818.75) when I hit save, the transaction is now in my expenses as a bill payment with the amount of negative $818.75. 

Hoping you can let me know what I am doing wrong?

I also tried manually matching the bills to the expense in the receipts for review. I could find all of the the bills, but when I tried to match them I got a noticing saying I could only match one transaction. I tried this in private window as well. Just not really sure what to do from here

Thank you for your time.