diff --git a/src/Gui/ApplicationPy.cpp b/src/Gui/ApplicationPy.cpp
index 6b04456f78..d0d5678179 100644
--- a/src/Gui/ApplicationPy.cpp
+++ b/src/Gui/ApplicationPy.cpp
@@ -1377,6 +1377,8 @@ PyObject* Application::sShowPreferences(PyObject * /*self*/, PyObject *args)
     wc.restoreCursor();
     cDlg.exec();
     wc.setWaitCursor();
+    cDlg.isRebootRequired(); //The user may have applied first, then clicked the cancel button so it's not in the if(cDlg.exec())
+    wc.setWaitCursor();
 
     Py_Return;
 }
diff --git a/src/Gui/CommandStd.cpp b/src/Gui/CommandStd.cpp
index 4141b754fd..9af6dab2cf 100644
--- a/src/Gui/CommandStd.cpp
+++ b/src/Gui/CommandStd.cpp
@@ -383,6 +383,7 @@ void StdCmdDlgPreferences::activated(int iMsg)
     if (cDlg.exec()) {
         cDlg.activeGroupPage(groupName, index);
     }
+    cDlg.isRebootRequired(); //The user may have applied first, then clicked the cancel button so it's not in the if(cDlg.exec())
 }
 
 //===========================================================================
diff --git a/src/Gui/DlgPreferencesImp.cpp b/src/Gui/DlgPreferencesImp.cpp
index e2b98f5c60..53a2df622c 100644
--- a/src/Gui/DlgPreferencesImp.cpp
+++ b/src/Gui/DlgPreferencesImp.cpp
@@ -32,6 +32,8 @@
 # include <QScreen>
 # include <QScrollArea>
 # include <QScrollBar>
+# include <QTimer>
+# include <QProcess>
 #endif
 
 #include <App/Application.h>
@@ -67,7 +69,7 @@ DlgPreferencesImp* DlgPreferencesImp::_activeDialog = nullptr;
  */
 DlgPreferencesImp::DlgPreferencesImp(QWidget* parent, Qt::WindowFlags fl)
     : QDialog(parent, fl), ui(new Ui_DlgPreferences),
-      invalidParameter(false), canEmbedScrollArea(true)
+      invalidParameter(false), canEmbedScrollArea(true), rebootRequired(false)
 {
     ui->setupUi(this);
     QFontMetrics fm(font());
@@ -458,8 +460,10 @@ void DlgPreferencesImp::applyChanges()
         auto tabWidget = static_cast<QTabWidget*>(ui->tabWidgetStack->widget(i));
         for (int j=0; j<tabWidget->count(); j++) {
             auto page = qobject_cast<PreferencePage*>(tabWidget->widget(j));
-            if (page)
+            if (page) {
                 page->saveSettings();
+                rebootRequired = rebootRequired || page->isRebootRequired();
+            }
         }
     }
 
@@ -471,6 +475,34 @@ void DlgPreferencesImp::applyChanges()
     }
 }
 
+void DlgPreferencesImp::isRebootRequired()
+{
+    if (rebootRequired) {
+        QMessageBox* restartBox = new QMessageBox();
+        restartBox->setIcon(QMessageBox::Warning);
+        restartBox->setWindowTitle(tr("Restart required"));
+        restartBox->setText(tr("You must restart FreeCAD for changes to take effect."));
+        restartBox->setStandardButtons(QMessageBox::Ok | QMessageBox::Cancel);
+        restartBox->setDefaultButton(QMessageBox::Cancel);
+        auto okBtn = restartBox->button(QMessageBox::Ok);
+        auto cancelBtn = restartBox->button(QMessageBox::Cancel);
+        okBtn->setText(tr("Restart now"));
+        cancelBtn->setText(tr("Restart later"));
+
+        int exec = restartBox->exec();
+
+        if (exec == QMessageBox::Ok) {
+            //restart FreeCAD after a delay to give time to this dialog to close
+            QTimer::singleShot(1000, []() 
+            {
+                QStringList args = QApplication::arguments();
+                if (getMainWindow()->close())
+                    QProcess::startDetached(QApplication::applicationFilePath(), args);
+            });
+        }
+    }
+}
+
 void DlgPreferencesImp::showEvent(QShowEvent* ev)
 {
     this->adjustSize();
diff --git a/src/Gui/DlgPreferencesImp.h b/src/Gui/DlgPreferencesImp.h
index 2c5de5d002..0b71d7067c 100644
--- a/src/Gui/DlgPreferencesImp.h
+++ b/src/Gui/DlgPreferencesImp.h
@@ -125,6 +125,7 @@ public:
     void reload();
     void activateGroupPage(const QString& group, int index);
     void activeGroupPage(QString& group, int& index) const;
+    void isRebootRequired();
 
 protected:
     void changeEvent(QEvent *e) override;
@@ -160,6 +161,7 @@ private:
     std::unique_ptr<Ui_DlgPreferences> ui;
     bool invalidParameter;
     bool canEmbedScrollArea;
+    bool rebootRequired;
 
     static const int GroupNameRole; /**< A name for our Qt::UserRole, used when storing user data in a list item */
 
diff --git a/src/Gui/DlgSettingsWorkbenches.ui b/src/Gui/DlgSettingsWorkbenches.ui
index a92c528dda..f21e38e188 100644
--- a/src/Gui/DlgSettingsWorkbenches.ui
+++ b/src/Gui/DlgSettingsWorkbenches.ui
@@ -29,7 +29,7 @@
       </size>
      </property>
      <property name="text">
-      <string>&lt;html&gt;&lt;head/&gt;&lt;body&gt;&lt;p&gt;You can enable, disable and reorder workbenches (requires restart). Additional workbenches can be installed through the addon manager.&lt;/p&gt;&lt;p&gt;
+      <string>&lt;html&gt;&lt;head/&gt;&lt;body&gt;&lt;p&gt;You can reorder workbenches by drag and drop. Additional workbenches can be installed through the addon manager.&lt;/p&gt;&lt;p&gt;
 Currently, your system has the following workbenches:&lt;/p&gt;&lt;/body&gt;&lt;/html&gt;</string>
      </property>
      <property name="wordWrap">
diff --git a/src/Gui/DlgSettingsWorkbenchesImp.cpp b/src/Gui/DlgSettingsWorkbenchesImp.cpp
index 657378b923..87325e126e 100644
--- a/src/Gui/DlgSettingsWorkbenchesImp.cpp
+++ b/src/Gui/DlgSettingsWorkbenchesImp.cpp
@@ -180,7 +180,7 @@ void wbListItem::setStartupWb(bool val)
         autoloadCheckBox->setChecked(true);
 
     enableCheckBox->setEnabled(!val);
-    autoloadCheckBox->setEnabled(!val);
+    autoloadCheckBox->setEnabled(!val && textLabel->isEnabled());
 }
 
 void wbListItem::setShortcutLabel(int index)
@@ -236,8 +236,8 @@ DlgSettingsWorkbenchesImp::DlgSettingsWorkbenchesImp( QWidget* parent )
     ui->wbList->setDefaultDropAction(Qt::MoveAction);
 
     connect(ui->wbList->model(), &QAbstractItemModel::rowsMoved, this, &DlgSettingsWorkbenchesImp::wbItemMoved);
-
-    connect(ui->AutoloadModuleCombo, QOverload<int>::of(&QComboBox::activated), this, [this](int index) { onStartWbChanged(index); });
+    connect(ui->AutoloadModuleCombo, QOverload<int>::of(&QComboBox::activated), this, &DlgSettingsWorkbenchesImp::onStartWbChanged);
+    connect(ui->WorkbenchSelectorPosition, QOverload<int>::of(&QComboBox::activated), this, &DlgSettingsWorkbenchesImp::onWbSelectorChanged);
 }
 
 /**
@@ -330,6 +330,8 @@ Build the list of unloaded workbenches.
 */
 void DlgSettingsWorkbenchesImp::buildWorkbenchList()
 {
+    QSignalBlocker sigblk(ui->wbList);
+
     QStringList workbenches = Application::Instance->workbenches();
     QStringList enabledWbs = getEnabledWorkbenches();
     QStringList disabledWbs = getDisabledWorkbenches();
@@ -437,6 +439,8 @@ void DlgSettingsWorkbenchesImp::saveWorkbenchSelector()
 
 void DlgSettingsWorkbenchesImp::loadWorkbenchSelector()
 {
+    QSignalBlocker sigblk(ui->WorkbenchSelectorPosition);
+
     //workbench selector position combobox setup
     ui->WorkbenchSelectorPosition->clear();
     ui->WorkbenchSelectorPosition->addItem(tr("Toolbar"));
@@ -447,6 +451,8 @@ void DlgSettingsWorkbenchesImp::loadWorkbenchSelector()
 
 void DlgSettingsWorkbenchesImp::wbToggled(const QString& wbName, bool enabled)
 {
+    requireReboot();
+
     setStartWorkbenchComboItems();
 
     //reorder the list of items.
@@ -519,6 +525,7 @@ void DlgSettingsWorkbenchesImp::setStartWorkbenchComboItems()
 
 void DlgSettingsWorkbenchesImp::wbItemMoved()
 {
+    requireReboot();
     for (int i = 0; i < ui->wbList->count(); i++) {
         wbListItem* wbItem = dynamic_cast<wbListItem*>(ui->wbList->itemWidget(ui->wbList->item(i)));
         if (wbItem) {
@@ -527,7 +534,7 @@ void DlgSettingsWorkbenchesImp::wbItemMoved()
     }
 }
 
-void Gui::Dialog::DlgSettingsWorkbenchesImp::onStartWbChanged(int index)
+void DlgSettingsWorkbenchesImp::onStartWbChanged(int index)
 {
     //Update _startupModule
     QVariant data = ui->AutoloadModuleCombo->itemData(index);
@@ -543,5 +550,10 @@ void Gui::Dialog::DlgSettingsWorkbenchesImp::onStartWbChanged(int index)
     }
 }
 
+void Gui::Dialog::DlgSettingsWorkbenchesImp::onWbSelectorChanged(int index)
+{
+    requireReboot();
+}
+
 #include "moc_DlgSettingsWorkbenchesImp.cpp"
 #include "DlgSettingsWorkbenchesImp.moc"
\ No newline at end of file
diff --git a/src/Gui/DlgSettingsWorkbenchesImp.h b/src/Gui/DlgSettingsWorkbenchesImp.h
index 9a790ef822..4d0fd86d61 100644
--- a/src/Gui/DlgSettingsWorkbenchesImp.h
+++ b/src/Gui/DlgSettingsWorkbenchesImp.h
@@ -52,6 +52,8 @@ public:
 protected Q_SLOTS:
     void wbToggled(const QString& wbName, bool enabled);
     void wbItemMoved();
+    void onWbSelectorChanged(int index);
+    void onStartWbChanged(int index);
 
 protected:
     void buildWorkbenchList();
@@ -65,7 +67,6 @@ private:
     void saveWorkbenchSelector();
     void loadWorkbenchSelector();
 
-    void onStartWbChanged(int index);
 
     std::vector<std::string> _backgroundAutoloadedModules;
     std::string _startupModule;
diff --git a/src/Gui/PropertyPage.cpp b/src/Gui/PropertyPage.cpp
index a26772c23e..8c5154176b 100644
--- a/src/Gui/PropertyPage.cpp
+++ b/src/Gui/PropertyPage.cpp
@@ -96,7 +96,7 @@ void PropertyPage::onReset()
 // ----------------------------------------------------------------
 
 /** Construction */
-PreferencePage::PreferencePage(QWidget* parent) : QWidget(parent)
+PreferencePage::PreferencePage(QWidget* parent) : QWidget(parent), rebootRequired(false)
 {
 }
 
@@ -105,6 +105,18 @@ void PreferencePage::changeEvent(QEvent* event)
     QWidget::changeEvent(event);
 }
 
+bool PreferencePage::isRebootRequired()
+{
+    return rebootRequired;
+}
+
+void PreferencePage::requireReboot()
+{
+    rebootRequired = true;
+}
+
+
+
 // ----------------------------------------------------------------
 
 PreferenceUiForm::PreferenceUiForm(const QString& fn, QWidget* parent)
diff --git a/src/Gui/PropertyPage.h b/src/Gui/PropertyPage.h
index 1794c6800f..4afafaa42c 100644
--- a/src/Gui/PropertyPage.h
+++ b/src/Gui/PropertyPage.h
@@ -71,12 +71,18 @@ public:
     explicit PreferencePage(QWidget* parent = nullptr);
     ~PreferencePage() override = default;
 
+    bool isRebootRequired();
+    void requireReboot();
+
 public Q_SLOTS:
     virtual void loadSettings()=0;
     virtual void saveSettings()=0;
 
 protected:
     void changeEvent(QEvent* event) override = 0;
+
+private:
+    bool rebootRequired;
 };
 
 /** Subclass that embeds a form from a UI file.