To reproduce: - Copy the content from the attached document - do not copy the last row. - Remove the bookmarks like this: bookmarks = radRichTextEditor1.Document.GetAllBookmarks().ToArray(); foreach (BookmarkRangeStart item in bookmarks) { radRichTextEditor1.Document.GoToBookmark(item); radRichTextEditor1.DocumentEditor.DeleteBookmark(item); } Workaround: var invalidStarts = this.radRichTextBox.Document .EnumerateChildrenOfType<BookmarkRangeStart>() .Where(start => start.End == null) .ToList(); foreach (var invalidStart in invalidStarts) { invalidStart.Parent.Children.Remove(invalidStart); } Note that when this workaround is used the document history will be deleted as well, which means that the undo operation will no longer hold information for previous operations