More details, please. Do you use Quicken Mac or Quicken for Windows? US or Canadian version? What version, edition level and release of Quicken are you using? Click Help / About Quicken (Mac: Quicken / About Quicken) to get this information. What version of Windows or Mac OS are you using?
Make sure that at least one of your printers is marked as Windows Default Printer ... doesn't have to be the one you want to use with Quicken, but you need at least one marked Default Printer
In some of the newer versions of Windows 10 you may also need to do this: Go into Windows Settings or Control Panel, Printers & Scanners. Uncheck "Let Windows manage my default printer".