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Why can't I pay bills directly with Quicken Billpay in the Bills Screen?

Quicken BillPay seems very complicated..
It works if I bring up a check and fill it out and it enters into my checking register. When the payment goes out, it never matches to the entry in my register.

But, if I start from the Bill screen and see a bill. It will let me enter into the register but says that I have to go to Billpay in order to send a payment. Seems that this should be more seamless. Am I doing something wrong?
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