Thank you for taking the time to report this issue to the Community, although I apologize that you have not yet received a response.
If you are still needing assistance with sending payments in Quicken, please take a moment and review the information available here, and post back to let us know what version and release of Quicken you are using.
Please also let us know what is happening when you try to send multiple payments. Do you receive any type of error message or code? Or does it look like the payment sent successfully but the status doesn't change from Send to Sent?
The more information you can provide regarding this issue will help the Community to better understand and assist.