When the "draw" widget is used, I think it creates a temporary sketch layer on the client itself (your browser).
and the print widget is invoking a print geoprocessing task on ArcGIS Server. The server itself is "building" the print PDF (gathering all the layers, the template, logo. north arrow, and then returning a URL to the PDF).
The server can't draw what is local on the client's memory browser.
They (Esri) need to improve the print widget to send out the Drawing Layer as JSON (line/polygon/text,etc. with all of the symbology you selected while drawing your markups on the map).
..and I am going to guess that they would need to send all the points, lines and polygons as a separate layer for the Server' GPTask to overlay them on top of your printed pdf map.
And the font text would be a bit complicated (size) because the print is 150dpi or 300dpi and the screen is 92dpi 🙂
What do they do in Councils? > print-screen 🙂 and paste in MsPaint.
