diff --git a/klipper/history.cpp b/klipper/history.cpp
index 9640c23b0..36b00e90e 100644
--- a/klipper/history.cpp
+++ b/klipper/history.cpp
@@ -140,8 +140,19 @@ void History::slotMoveToTop(QAction* action) {
 }
 
 void History::slotMoveToTop(const QByteArray& uuid) {
+    const QModelIndex item = m_model->indexOf(uuid);
+    if (item.isValid() && item.row() == 0) {
+        // The item is already at the top, but it still may be not be set as the actual clipboard
+        // contents, normally this happens if the item is only in the X11 mouse selection but
+        // not in the Ctrl+V clipboard.
+        emit topChanged();
+        m_topIsUserSelected = true;
+        emit topIsUserSelectedSet();
+        return;
+    }
     m_model->moveToTop(uuid);
     m_topIsUserSelected = true;
+    emit topIsUserSelectedSet();
 }
 
 void History::setMaxSize( unsigned max_size ) {
diff --git a/klipper/history.h b/klipper/history.h
index 7690ffdc1..7001450fc 100644
--- a/klipper/history.h
+++ b/klipper/history.h
@@ -136,6 +136,7 @@ Q_SIGNALS:
      */
     void topChanged();
 
+    void topIsUserSelectedSet();
 
 private:
     /**
diff --git a/klipper/klipper.cpp b/klipper/klipper.cpp
index 4703227ef..30f3e5815 100644
--- a/klipper/klipper.cpp
+++ b/klipper/klipper.cpp
@@ -117,6 +117,7 @@ Klipper::Klipper(QObject* parent, const KSharedConfigPtr& config, KlipperMode mo
     m_popup = new KlipperPopup(m_history);
     m_popup->setShowHelp(m_mode == KlipperMode::Standalone);
     connect(m_history, &History::changed, m_popup, &KlipperPopup::slotHistoryChanged);
+    connect(m_history, &History::topIsUserSelectedSet, m_popup, &KlipperPopup::slotTopIsUserSelectedSet);
 
     // we need that collection, otherwise KToggleAction is not happy :}
     m_collection = new KActionCollection( this );
diff --git a/klipper/klipperpopup.cpp b/klipper/klipperpopup.cpp
index 12d3205d9..e0d35e56c 100644
--- a/klipper/klipperpopup.cpp
+++ b/klipper/klipperpopup.cpp
@@ -175,6 +175,13 @@ void KlipperPopup::rebuild( const QString& filter ) {
     m_dirty = false;
 }
 
+void KlipperPopup::slotTopIsUserSelectedSet() {
+    if ( !m_dirty && m_nHistoryItems > 0 && history()->topIsUserSelected() ) {
+        actions().at(TOP_HISTORY_ITEM_INDEX)->setCheckable(true);
+        actions().at(TOP_HISTORY_ITEM_INDEX)->setChecked(true);
+    }
+}
+
 void KlipperPopup::plugAction( QAction* action ) {
     m_actions.append(action);
 }
diff --git a/klipper/klipperpopup.h b/klipper/klipperpopup.h
index 3ba3d97b3..cf70ab977 100644
--- a/klipper/klipperpopup.h
+++ b/klipper/klipperpopup.h
@@ -61,6 +61,7 @@ public:
     }
 public Q_SLOTS:
     void slotHistoryChanged() { m_dirty = true; }
+    void slotTopIsUserSelectedSet();
     void slotAboutToShow();
     /**
      * set the top history item active, to easy kb navigation