I created a map template with a legend (first picture). Then I created a print service using the following tutorial : http://server.arcgis.com/en/server/latest/get-started/windows/tutorial-publishing-additional-services-for-printing.htm .
I included the template (steps 8 & 9 in tutorial) and completed the process.
When I run my web page, and use the print service I created, the legend doesn't show up the way I thought it would show up (second picture). The second and third layer's headings are disappearing. Not sure why. Has anyone had a similar experience ?