That sounds like you're using Direct Connect to send the billpay instructions directly to your bank ... and not using Quicken BillPay, a separate product offered by Metavante.
I am using Quicken Premier 2019. When I press the check # there in no "send" to select. When I fill it in and try to send a check, it states that I am not set up for online payments. What needs to be activated to enable this process with my bank?
I would select "Send" in the check column and provide the name and address of the payee. It would be sent to my bank when I selected the "Online Center". Once uploaded my Quicken would be updated with a check number where "Send" was originally. I would put every check I wanted to send in manually using my Memorized Payees.
There is no reason to use Chase site. They are a free Direct Connect FI. You simply create the Online Payees you want to pay.
@ps56k no need to upgrade. I've used this functionality in Deluxe for years. Chase and PNC are the only banks I'm aware of that offer this for free.