Try resetting your printer definitions in Quicken and then redefine the printer:
For Quicken for Windows versions 2009 and older:
For Quicken for Windows 2010 and newer:
Printer Setup (all versions):
If you're printing checks, do not forget to select the correct check style.
(Optional) If you are printing a logo (image) on your checks, click the Logo button and make sure that your logo image file is still where Quicken expects it to be. Also choose the proper features for printing partial pages when using 3-per-page stock. Users of continuous forms on dot matrix printers: Be sure to select "Continuous Forms" instead of "Page-oriented".
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".