Instead of wrestling with the vagaries of Bill Manager, how about this alternative … Personally, I don't use Bill Pay / Bill Manager at all. Since time "B.I." (before the Internet was invented) I have set up almost all of my recurring payments as Direct Debit, PAC Draft, Autopay, whatever the biller calls it. The payment is automatically debited from my checking or credit card account by the biller on due date. And in most cases there's no transaction fee*. When I get notified about a new statement having arrived, all I have to do in Quicken is to run a regular scheduled reminder to pay the amount due. Haven't missed a payment in many years.
*Some companies may charge for withdrawals from credit cards, but offer direct debit from checking accounts for free … or vice versa … read the fine print on the biller's website to choose the no-fee option