I would recommend running the Validate & Repair tool on the data file from the File menu > File Operations > Validate & Repair option.
In the Validate File window that opens, click the top box to "validate file" and then click OK.
When the validation completes, a data log will open in Notepad, please let us know if any errors or issues are found/repaired, and when ready close and re-open Quicken.
Please let us know what you find!
-Quicken Tyka
Thank you for taking the time to visit the Community to report your issue, although I apologize that you have not yet received a response.
We'll need a bit more information to be able to assist. What type of bill is this happening to? Is this Income, Transfer for just ordinary bills?
Is this an online bill or a manual bill? What are current auto-enter settings or this bill?
The more information you can provide regarding this issue will help the Community to better understand and assist.
Thank you,