diff --git a/src/Libraries/ICSharpCode.TextEditor/Project/Src/Gui/TextAreaClipboardHandler.cs b/src/Libraries/ICSharpCode.TextEditor/Project/Src/Gui/TextAreaClipboardHandler.cs
index e945e04796..ea7b82bdc4 100644
--- a/src/Libraries/ICSharpCode.TextEditor/Project/Src/Gui/TextAreaClipboardHandler.cs
+++ b/src/Libraries/ICSharpCode.TextEditor/Project/Src/Gui/TextAreaClipboardHandler.cs
@@ -87,10 +87,27 @@ namespace ICSharpCode.TextEditor
 					dataObject.SetData(DataFormats.Rtf, RtfWriter.GenerateRtf(textArea));
 				}
 				OnCopyText(new CopyTextEventArgs(str));
-				Clipboard.SetDataObject(dataObject, true, 50, 50);
-				return true;
+				
+				// Work around ExternalException bug. (SD2-426)
+				// Best reproducable inside Virtual PC.
+				// SetDataObject has "retry" parameters, but apparently a call to "DoEvents"
+				// is necessary for the workaround to work.
+				int i = 0;
+				while (true) {
+					try {
+						Clipboard.SetDataObject(dataObject, true, 5, 50);
+						return true;
+					} catch (ExternalException) {
+						if (i++ > 5)
+							throw;
+					}
+					System.Threading.Thread.Sleep(50);
+					Application.DoEvents();
+					System.Threading.Thread.Sleep(50);
+				}
+			} else {
+				return false;
 			}
-			return false;
 		}
 		
 		public void Cut(object sender, EventArgs e)
diff --git a/src/Main/Core/Project/Src/Util/ClipboardWrapper.cs b/src/Main/Core/Project/Src/Util/ClipboardWrapper.cs
index 8f49232277..4c06870d22 100644
--- a/src/Main/Core/Project/Src/Util/ClipboardWrapper.cs
+++ b/src/Main/Core/Project/Src/Util/ClipboardWrapper.cs
@@ -19,6 +19,7 @@ namespace ICSharpCode.Core
 		public static bool ContainsText {
 			get {
 				try {
+					LoggingService.Debug("ContainsText called");
 					return Clipboard.ContainsText();
 				} catch (ExternalException) {
 					return false;
@@ -55,7 +56,19 @@ namespace ICSharpCode.Core
 		
 		public static void SetDataObject(object data)
 		{
-			Clipboard.SetDataObject(data, true, 50, 50);
+			int i = 0;
+			while (true) {
+				try {
+					Clipboard.SetDataObject(data, true, 5, 50);
+					return;
+				} catch (ExternalException) {
+					if (i++ > 5)
+						throw;
+				}
+				System.Threading.Thread.Sleep(50);
+				Application.DoEvents();
+				System.Threading.Thread.Sleep(50);
+			}
 		}
 	}
 }