diff --git a/src/libraries/System.Drawing.Common/src/System/Drawing/Printing/DefaultPrintController.cs b/src/libraries/System.Drawing.Common/src/System/Drawing/Printing/DefaultPrintController.cs
index 6999d9048e66c..1a78f2e4ebe7e 100644
--- a/src/libraries/System.Drawing.Common/src/System/Drawing/Printing/DefaultPrintController.cs
+++ b/src/libraries/System.Drawing.Common/src/System/Drawing/Printing/DefaultPrintController.cs
@@ -22,13 +22,13 @@ public class StandardPrintController : PrintController
         public override void OnStartPrint(PrintDocument document, PrintEventArgs e)
         {
             Debug.Assert(_dc == null && _graphics == null, "PrintController methods called in the wrong order?");
-            Debug.Assert(_modeHandle != null);
 
             base.OnStartPrint(document, e);
             // the win32 methods below SuppressUnmanagedCodeAttributes so assertin on UnmanagedCodePermission is redundant
             if (!document.PrinterSettings.IsValid)
                 throw new InvalidPrinterException(document.PrinterSettings);
 
+            Debug.Assert(_modeHandle != null, "_modeHandle should have been set by PrintController.OnStartPrint");
             _dc = document.PrinterSettings.CreateDeviceContext(_modeHandle);
             Interop.Gdi32.DOCINFO info = new Interop.Gdi32.DOCINFO();
             info.lpszDocName = document.DocumentName;
diff --git a/src/libraries/System.Drawing.Common/tests/Printing/PrintDocumentTests.cs b/src/libraries/System.Drawing.Common/tests/Printing/PrintDocumentTests.cs
index 64bff89aaa013..7a96b12c43244 100644
--- a/src/libraries/System.Drawing.Common/tests/Printing/PrintDocumentTests.cs
+++ b/src/libraries/System.Drawing.Common/tests/Printing/PrintDocumentTests.cs
@@ -23,11 +23,12 @@
 // WITH THE SOFTWARE OR THE USE OR OTHER DEALINGS IN THE SOFTWARE.
 //
 
+using System.IO;
 using Xunit;
 
 namespace System.Drawing.Printing.Tests
 {
-    public class PrintDocumentTests
+    public class PrintDocumentTests : FileCleanupTestBase
     {
         private readonly PageSettings _pageSettings = new PageSettings()
         {
@@ -184,6 +185,26 @@ public void EndPrint_SetValue_ReturnsExpected()
             }
         }
 
+        [ConditionalFact(nameof(CanPrintToPdf))]
+        public void Print_DefaultPrintController_Success()
+        {
+            bool endPrintCalled = false;
+            var endPrintHandler = new PrintEventHandler((sender, e) => endPrintCalled = true);
+            using (var document = new PrintDocument())
+            {
+                document.PrinterSettings.PrinterName = PrintToPdfPrinterName;
+                document.PrinterSettings.PrintFileName = GetTestFilePath();
+                document.PrinterSettings.PrintToFile = true;
+                document.EndPrint += endPrintHandler;
+                document.Print();
+                document.EndPrint -= endPrintHandler;
+            }
+
+            // File may not have finished saving to disk when Print returns,
+            // so we check for EndPrint being called instead of file existence.
+            Assert.True(endPrintCalled);
+        }
+
         [ActiveIssue("https://github.com/dotnet/runtime/issues/26428")]
         [ConditionalFact(Helpers.AnyInstalledPrinters, Helpers.IsDrawingSupported)]
         public void PrintPage_SetValue_ReturnsExpected()
@@ -253,6 +274,23 @@ private void AssertDefaultPageSettings(PageSettings pageSettings)
             Assert.True(pageSettings.PrinterSettings.IsDefaultPrinter);
         }
 
+        private const string PrintToPdfPrinterName = "Microsoft Print to PDF";
+        private static bool CanPrintToPdf()
+        {
+            if (!PlatformDetection.IsWindows || !PlatformDetection.IsDrawingSupported)
+                return false;
+
+            foreach (string name in PrinterSettings.InstalledPrinters)
+            {
+                if (name == PrintToPdfPrinterName)
+                {
+                    return true;
+                }
+            }
+
+            return false;
+        }
+
         private class TestPrintController : PrintController
         {
             public override Graphics OnStartPage(PrintDocument document, PrintPageEventArgs e)