Description and workaround: It appears that Outlook produces different RTF contents when using its different Copy commands. In some cases the RTF string produced by Outlook contains empty spans which is not a valid element in our implementation. To handle that case, you can subscribe to the CommandExecuting event to capture the Paste command before it was executed, strip the empty spans, and then modify the clipboard contents with a valid RTF string. Additionally, when you try to delete the text of pasted hyperlinks using backspace, an exception will be thrown at some point (for example, after pasting the link \\server\folder1\somefile.txt and deleting the dot). The following code snippet demonstrates how to handle deleting pasted links: Private Sub radRichTextEditor1_CommandExecuting(sender As Object, e As CommandExecutingEventArgs) Handles radRichTextEditor1.CommandExecuting If TypeOf e.Command Is DeleteCommand Me.RadRichTextEditor1.RichTextBoxElement.InvalidateMeasure(true) Me.RadRichTextEditor1.RichTextBoxElement.UpdateLayout() End If End Sub The following code snippet demonstrates how to handle removing empty spans: Private Sub radRichTextEditor1_CommandExecuting(sender As Object, e As CommandExecutingEventArgs) Handles radRichTextEditor1.CommandExecuting If Not (TypeOf e.Command Is PasteCommand) Then Return End If Dim docString As String = Nothing Dim docObj As Object = Clipboard.GetData("Rich Text Format") If docObj IsNot Nothing AndAlso docObj.[GetType]() = GetType(String) Then docString = DirectCast(docObj, String) End If Dim document As RadDocument = Nothing Using stream As New MemoryStream() Dim writer As New StreamWriter(stream) writer.Write(docString) writer.Flush() stream.Seek(0, SeekOrigin.Begin) Try document = New RtfFormatProvider().Import(stream) Catch ex As Exception System.Diagnostics.Debug.WriteLine("Error reading document from clipboard:" & vbLf + ex.ToString()) End Try End Using If document IsNot Nothing Then Dim emptySpans As New List(Of Span)() For Each span As var In document.EnumerateChildrenOfType(Of Span)() If [String].IsNullOrEmpty(span.Text) Then emptySpans.Add(span) End If Next If emptySpans.Count = 0 Then Return End If For Each span As var In emptySpans span.Parent.Children.Remove(span) Next Dim modifiedRtf As String = New RtfFormatProvider().Export(document) Clipboard.SetData("Rich Text Format", modifiedRtf) End If End Sub