When trying to import a document containing bookmark and BookmarkRangeEnd is after the last paragraph, a StackOverflowException is thrown in IntervalNode while trying to rebuild the document cache. (RadDocumentChildrenCache.RebuildTree()). The same could be observed if the bookmark end is last in the header/footer, between table cells in the RadDocument body, or when all paragraphs after the bookmark range end are hidden (with vanish property). Workaround: Detect the problematic annotations and remove them: foreach (var rangeStart in document.EnumerateChildrenOfType<AnnotationRangeStart>()) { if (rangeStart.End == null || rangeStart.End.Parent == null || rangeStart.End.Parent.Parent == null) { //MessageBox.Show("This indicates a problem."); rangeStart.Parent.Children.Remove(rangeStart); } } Note: Until 2017 R2 SP1 release StackOverflowException is thrown, after this release an ArgumentException should be thrown.