To avoid missed or late payments I recommend you logon directly to the biller's website and authorize them to direct debit (aka PAC Draft, Autopay, APS, etc.) the next and all future payments from your checking account or a credit card. (This also applies to making credit card payments) The biller will do all the work for you and make an electronic debit on the due date and you don't have to worry about being late.
In Quicken unlink the bill and just record a scheduled reminder which does not execute as an online payment into your account register on or before the Due Date and before you download transactions from the bank or credit card containing the payment transaction. That will allow Quicken to match your register transaction to the downloaded data and not cause any further issues.