Thanks for the immediate response, @A Notary Company.
Let me help provide additional information about money out type of transactions.
The program analyzes the data and matches it with the existing entries. It'll look for the manually created payments and expenses entered with Check or Expense. With this, you should be able to match not just the unpaid bills but the bill payments as well.
I'd also recommend contacting our Online Support, so they can investigate your issue further in a secure environment. Please keep me updated on how it goes.
I'll be here to keep helping should you have any additional questions.