ADDITIONAL SYSTEM INFORMATION :
Windows 10.0.18363.778

java version "14.0.1" 2020-04-14
Java(TM) SE Runtime Environment (build 14.0.1+7)
Java HotSpot(TM) 64-Bit Server VM (build 14.0.1+7, mixed mode, sharing)

also:

openjdk version "1.8.0_252"
OpenJDK Runtime Environment Corretto-8.252.09.2 (build 1.8.0_252-b09)
OpenJDK 64-Bit Server VM Corretto-8.252.09.2 (build 25.252-b09, mixed mode)

A DESCRIPTION OF THE PROBLEM :
When the graphics device has an empty clipping path, this is ignored when printing. Doing the same when rendering in a BufferedImage works as expected. "Empty clipping" path means that "graphics.getClip().getPathIterator(null).isDone()" is true.

STEPS TO FOLLOW TO REPRODUCE THE PROBLEM :
run the program
in the dialogbox, choose PDF or XPS
choose the filename

(it also reproduces with a real printer, but you may want to save toner / ink / paper)

EXPECTED VERSUS ACTUAL BEHAVIOR :
EXPECTED -
the PDF / XPS file should be blank
ACTUAL -
the PDF / XPS file is red

---------- BEGIN SOURCE ----------
package pdfbox4822clip;

import java.awt.Color;
import java.awt.Graphics;
import java.awt.Graphics2D;
import java.awt.Rectangle;
import java.awt.geom.Area;
import java.awt.geom.Rectangle2D;
import java.awt.image.BufferedImage;
import java.awt.print.PageFormat;
import java.awt.print.Printable;
import java.awt.print.PrinterException;
import java.awt.print.PrinterJob;
import java.io.File;
import java.io.IOException;
import javax.imageio.ImageIO;
import javax.print.PrintServiceLookup;

public class PDFBox4822Clip implements Printable
{

    public static void main(String[] args) throws PrinterException, IOException
    {
        PDFBox4822Clip main = new PDFBox4822Clip();
        main.paintToImage(); // produces transparent image
        main.paintToPrint(); // produces red page, but should produce
    }

    public PDFBox4822Clip()
    {
        System.out.println("Empty Area path empty? " + new Area().getPathIterator(null).isDone());
        System.out.println("Empty Rect path empty? " + new Rectangle().getPathIterator(null).isDone());
    }
    
    public void paintToPrint() throws PrinterException
    {
        PrinterJob job = PrinterJob.getPrinterJob();
        job.setPrintService(PrintServiceLookup.lookupDefaultPrintService());
        job.setPrintable(this);
        if (job.printDialog()) // Choose PDF or XPS
        {
            job.print();
        }
    }

    public void paintToImage() throws IOException
    {
        BufferedImage bim = new BufferedImage(596, 842, BufferedImage.TYPE_INT_ARGB);
        Graphics g2d = (Graphics2D) bim.getGraphics();
        
        paint(g2d);
        
        g2d.dispose();
        ImageIO.write(bim, "png", new File("PDFBox4822Clip.png"));
    }

    @Override
    public int print(Graphics graphics, PageFormat pageFormat, int pageIndex) throws PrinterException
    {
        if (pageIndex == 0)
        {
            paint(graphics);

            return PAGE_EXISTS;
        }
        return NO_SUCH_PAGE;
    }

    private void paint(Graphics g2d)
    {
        Rectangle2D r1 = new Rectangle(11, 74, 540, 750);
        Rectangle2D r2 = new Rectangle(374, 22, 8, 16);
        Area area = new Area(r1);
        area.intersect(new Area(r2));
        g2d.setClip(area); // area is empty
        System.out.println("g2d: " + g2d);
        System.out.println("clip empty? " + g2d.getClip().getPathIterator(null).isDone());
        System.out.println("clip bounds: " + g2d.getClip().getBounds2D());
        g2d.setColor(Color.red);
        g2d.fillRect(0, 0, 1000, 1000);
    }
}

---------- END SOURCE ----------

CUSTOMER SUBMITTED WORKAROUND :
before doing a graphics operation like fill(), do something like this:

if (graphics.getClip() != null && graphics.getClip().getPathIterator(null).isDone())
{
    graphics.setClip(new Rectangle());
}

This works because "new Rectangle()" does not have an empty path, unlike "new Area()".

FREQUENCY : always