diff --git a/Pdf4QtLib/sources/pdfitemmodels.cpp b/Pdf4QtLib/sources/pdfitemmodels.cpp
index 855ee30..1a8ffaa 100644
--- a/Pdf4QtLib/sources/pdfitemmodels.cpp
+++ b/Pdf4QtLib/sources/pdfitemmodels.cpp
@@ -522,6 +522,12 @@ void PDFOutlineTreeItemModel::setDestination(const QModelIndex& index, const PDF
     }
 }
 
+const PDFOutlineItem* PDFOutlineTreeItemModel::getRootOutlineItem() const
+{
+    PDFOutlineTreeItem* item = static_cast<PDFOutlineTreeItem*>(m_rootItem.get());
+    return item->getOutlineItem();
+}
+
 bool PDFOutlineTreeItemModel::setData(const QModelIndex& index, const QVariant& value, int role)
 {
     if (!m_editable || !index.isValid() || role != Qt::EditRole)
diff --git a/Pdf4QtLib/sources/pdfitemmodels.h b/Pdf4QtLib/sources/pdfitemmodels.h
index b4b0fce..f26fa25 100644
--- a/Pdf4QtLib/sources/pdfitemmodels.h
+++ b/Pdf4QtLib/sources/pdfitemmodels.h
@@ -211,6 +211,8 @@ public:
     void setFontItalics(const QModelIndex& index, bool value);
     void setDestination(const QModelIndex& index, const PDFDestination& destination);
 
+    const PDFOutlineItem* getRootOutlineItem() const;
+
 private:
     QIcon m_icon;
     bool m_editable;
diff --git a/Pdf4QtViewer/pdfprogramcontroller.h b/Pdf4QtViewer/pdfprogramcontroller.h
index 7e79e6c..ba051be 100644
--- a/Pdf4QtViewer/pdfprogramcontroller.h
+++ b/Pdf4QtViewer/pdfprogramcontroller.h
@@ -285,6 +285,7 @@ public:
     void performSaveAs();
 
     void onActionTriggered(const pdf::PDFAction* action);
+    void onDocumentModified(pdf::PDFModifiedDocument document);
     void updateActionsAvailability();
 
     bool getIsBusy() const;
@@ -356,7 +357,6 @@ private:
     void onDrawSpaceChanged();
     void onPageLayoutChanged();
     void onDocumentReadingFinished();
-    void onDocumentModified(pdf::PDFModifiedDocument document);
     void onDocumentUndoRedo(pdf::PDFModifiedDocument document);
     void onQueryPasswordRequest(QString* password, bool* ok);
     void onPageRenderingErrorsChanged(pdf::PDFInteger pageIndex, int errorsCount);
diff --git a/Pdf4QtViewer/pdfsidebarwidget.cpp b/Pdf4QtViewer/pdfsidebarwidget.cpp
index e06cb0d..4d2f0ba 100644
--- a/Pdf4QtViewer/pdfsidebarwidget.cpp
+++ b/Pdf4QtViewer/pdfsidebarwidget.cpp
@@ -31,6 +31,7 @@
 #include "pdfexception.h"
 #include "pdfsignaturehandler.h"
 #include "pdfdrawspacecontroller.h"
+#include "pdfdocumentbuilder.h"
 
 #include <QMenu>
 #include <QAction>
@@ -88,6 +89,10 @@ PDFSidebarWidget::PDFSidebarWidget(pdf::PDFDrawWidgetProxy* proxy,
         ui->bookmarksTreeView->setDragDropMode(QAbstractItemView::InternalMove);
         ui->bookmarksTreeView->setContextMenuPolicy(Qt::CustomContextMenu);
         connect(ui->bookmarksTreeView, &QTreeView::customContextMenuRequested, this, &PDFSidebarWidget::onBookmarksTreeViewContextMenuRequested);
+        connect(m_outlineTreeModel, &pdf::PDFOutlineTreeItemModel::dataChanged, this, &PDFSidebarWidget::onOutlineItemsChanged);
+        connect(m_outlineTreeModel, &pdf::PDFOutlineTreeItemModel::rowsInserted, this, &PDFSidebarWidget::onOutlineItemsChanged);
+        connect(m_outlineTreeModel, &pdf::PDFOutlineTreeItemModel::rowsRemoved, this, &PDFSidebarWidget::onOutlineItemsChanged);
+        connect(m_outlineTreeModel, &pdf::PDFOutlineTreeItemModel::rowsMoved, this, &PDFSidebarWidget::onOutlineItemsChanged);
     }
 
     connect(ui->bookmarksTreeView, &QTreeView::clicked, this, &PDFSidebarWidget::onOutlineItemClicked);
@@ -862,6 +867,19 @@ void PDFSidebarWidget::onBookmarksTreeViewContextMenuRequested(const QPoint& pos
     contextMenu.exec(ui->bookmarksTreeView->mapToGlobal(pos));
 }
 
+void PDFSidebarWidget::onOutlineItemsChanged()
+{
+    if (m_document)
+    {
+        pdf::PDFDocumentBuilder builder(m_document);
+        builder.setOutline(m_outlineTreeModel->getRootOutlineItem());
+
+        pdf::PDFDocumentPointer pointer(new pdf::PDFDocument(builder.build()));
+        pdf::PDFModifiedDocument document(qMove(pointer), m_optionalContentActivity, pdf::PDFModifiedDocument::None);
+        Q_EMIT documentModified(qMove(document));
+    }
+}
+
 void PDFSidebarWidget::paintEvent(QPaintEvent* event)
 {
     Q_UNUSED(event);
diff --git a/Pdf4QtViewer/pdfsidebarwidget.h b/Pdf4QtViewer/pdfsidebarwidget.h
index 4ecac46..1a215e3 100644
--- a/Pdf4QtViewer/pdfsidebarwidget.h
+++ b/Pdf4QtViewer/pdfsidebarwidget.h
@@ -100,6 +100,7 @@ public:
 
 signals:
     void actionTriggered(const pdf::PDFAction* action);
+    void documentModified(pdf::PDFModifiedDocument document);
 
 private:
     void updateGUI(Page preferredPage);
@@ -113,6 +114,7 @@ private:
     void onThumbnailClicked(const QModelIndex& index);
     void onSignatureCustomContextMenuRequested(const QPoint &pos);
     void onBookmarksTreeViewContextMenuRequested(const QPoint &pos);
+    void onOutlineItemsChanged();
 
     struct PageInfo
     {
diff --git a/Pdf4QtViewer/pdfviewermainwindow.cpp b/Pdf4QtViewer/pdfviewermainwindow.cpp
index 889bb34..5a242db 100644
--- a/Pdf4QtViewer/pdfviewermainwindow.cpp
+++ b/Pdf4QtViewer/pdfviewermainwindow.cpp
@@ -261,6 +261,7 @@ PDFViewerMainWindow::PDFViewerMainWindow(QWidget* parent) :
     addDockWidget(Qt::LeftDockWidgetArea, m_sidebarDockWidget);
     m_sidebarDockWidget->hide();
     connect(m_sidebarWidget, &PDFSidebarWidget::actionTriggered, m_programController, &PDFProgramController::onActionTriggered);
+    connect(m_sidebarWidget, &PDFSidebarWidget::documentModified, m_programController, &PDFProgramController::onDocumentModified);
 
     m_advancedFindWidget = new PDFAdvancedFindWidget(m_programController->getPdfWidget()->getDrawWidgetProxy(), this);
     m_advancedFindDockWidget = new QDockWidget(tr("Advanced find"), this);
diff --git a/Pdf4QtViewer/pdfviewermainwindowlite.cpp b/Pdf4QtViewer/pdfviewermainwindowlite.cpp
index 392d79f..23efb9a 100644
--- a/Pdf4QtViewer/pdfviewermainwindowlite.cpp
+++ b/Pdf4QtViewer/pdfviewermainwindowlite.cpp
@@ -196,6 +196,7 @@ PDFViewerMainWindowLite::PDFViewerMainWindowLite(QWidget* parent) :
     addDockWidget(Qt::LeftDockWidgetArea, m_sidebarDockWidget);
     m_sidebarDockWidget->hide();
     connect(m_sidebarWidget, &PDFSidebarWidget::actionTriggered, m_programController, &PDFProgramController::onActionTriggered);
+    connect(m_sidebarWidget, &PDFSidebarWidget::documentModified, m_programController, &PDFProgramController::onDocumentModified);
 
     ui->menuView->addSeparator();
     ui->menuView->addAction(m_sidebarDockWidget->toggleViewAction());