Workaround: private void RadRichTextEditor1_CommandExecuting(object sender, CommandExecutingEventArgs e) { if (!(e.Command is PasteCommand)) { return; } DocumentFragment res = ClipboardEx.GetDocumentFromClipboard("RadDocumentGUID"); if (res == null) { foreach (ClipboardHandler settings in ClipboardEx.ClipboardHandlers) { res = ClipboardEx.GetDocumentFromClipboard(settings.ClipboardDataFormat, settings.ClipboardStringFilter); } } if (res == null) { e.Cancel = true; System.Drawing.Image bitmapSource = Clipboard.GetImage(); if (bitmapSource == null) { return; } Telerik.WinForms.Documents.Layout.Padding sectionmargin = this.radRichTextEditor1.Document.CaretPosition.GetCurrentSectionBox().AssociatedSection.ActualPageMargin; double originalPixelWidth = bitmapSource.Width; double originalPixelHeight = bitmapSource.Height; if (originalPixelWidth == 0 || originalPixelHeight == 0) { originalPixelWidth = 10; originalPixelHeight = 10; } double width = originalPixelWidth; double height = originalPixelHeight; if (this.radRichTextEditor1.Document.LayoutMode == DocumentLayoutMode.Paged) { Section currentSection = this.radRichTextEditor1.Document.CaretPosition.GetCurrentSectionBox().AssociatedSection; Telerik.WinForms.Documents.Model.SizeF pageSize = (Telerik.WinForms.Documents.Model.SizeF)currentSection.GetType().GetProperty("ActualPageSize", System.Reflection.BindingFlags.Instance | System.Reflection.BindingFlags.NonPublic).GetValue(currentSection); double maxWidth = pageSize.Width - (sectionmargin.Left + sectionmargin.Right); double maxHeight = pageSize.Height - (sectionmargin.Top + sectionmargin.Bottom); width = Math.Min(maxWidth, width); height = Math.Min(maxHeight, height); } double ratio = originalPixelWidth / originalPixelHeight; width = Math.Min(width, height * ratio); height = width / ratio; Telerik.WinControls.RichTextEditor.UI.Size size = new Telerik.WinControls.RichTextEditor.UI.Size(width, height); ImageInline imageInline = new ImageInline(new WriteableBitmap(bitmapSource)); imageInline.Size = size; this.radRichTextEditor1.RichTextBoxElement.ActiveDocumentEditor.InsertInline(imageInline); } }