If you're able to update your accounts without an error, but you're unable to send a payment (through Quicken Bill Pay or your bank Bill Pay via Direct Connect), make sure the payment date is allowing enough time for the payment to be sent. If that doesn't resolve the issue, you'll need to contact your bank to make sure you're properly enrolled in their bill pay service.
To find the contact information for your bank, open Quicken and go to Tools > Online Center and click Contact Info at the top of the window after selecting your bank's name.
Lone time Quicken Home Business & Rental Property user with Chase Bank with all Quicken updates in place. Took a complete download of data from several different financial companies including Chase. The only error message was an OL-301-A for a single upload payment to a longtime vendor. Tired again by itself same error message. Any Ideas?