Solved! Go to Solution.
1. In order for you to add anything that not showing on the printout, more than likely, you will need to modify the MXD templates that served as the print page templates. You can find these templates under <arcgis server folder>/templates on your arcgis server machine. If you are using third party print url, that will be an unfortunate.
2. To add anything to your popup, you just need to modify the popup content.