diff --git a/src/kitemviews/kitemlistcontroller.cpp b/src/kitemviews/kitemlistcontroller.cpp
--- a/src/kitemviews/kitemlistcontroller.cpp
+++ b/src/kitemviews/kitemlistcontroller.cpp
@@ -61,6 +61,8 @@
             this, &KItemListController::slotChangeCurrentItem);
     connect(m_selectionManager, &KItemListSelectionManager::currentChanged,
             m_keyboardManager, &KItemListKeyboardSearchManager::slotCurrentChanged);
+    connect(m_selectionManager, &KItemListSelectionManager::selectionChanged,
+            m_keyboardManager, &KItemListKeyboardSearchManager::slotSelectionChanged);
 
     m_autoActivationTimer = new QTimer(this);
     m_autoActivationTimer->setSingleShot(true);
@@ -472,12 +474,12 @@
     if (!m_model || m_model->count() == 0) {
         return;
     }
-    const int currentIndex = m_selectionManager->currentItem();
     int index;
     if (searchFromNextItem) {
+        const int currentIndex = m_selectionManager->currentItem();
         index = m_model->indexForKeyboardSearch(text, (currentIndex + 1) % m_model->count());
     } else {
-        index = m_model->indexForKeyboardSearch(text, currentIndex);
+        index = m_model->indexForKeyboardSearch(text, 0);
     }
     if (index >= 0) {
         m_selectionManager->setCurrentItem(index);
diff --git a/src/kitemviews/private/kitemlistkeyboardsearchmanager.h b/src/kitemviews/private/kitemlistkeyboardsearchmanager.h
--- a/src/kitemviews/private/kitemlistkeyboardsearchmanager.h
+++ b/src/kitemviews/private/kitemlistkeyboardsearchmanager.h
@@ -24,6 +24,7 @@
 #define KITEMLISTKEYBOARDSEARCHMANAGER_H
 
 #include "dolphin_export.h"
+#include "kitemviews/kitemset.h"
 
 #include <QElapsedTimer>
 #include <QObject>
@@ -59,10 +60,12 @@
     qint64 timeout() const;
 
     void cancelSearch();
+    bool shouldClearSearchIfInputTimeReached();
 
 public slots:
 
     void slotCurrentChanged(int current, int previous);
+    void slotSelectionChanged(const KItemSet& current, const KItemSet& previous);
 
 signals:
     /**
@@ -78,6 +81,7 @@
 
 private:
     QString m_searchedString;
+    bool m_isSearchRestarted;
     QElapsedTimer m_keyboardInputTime;
     qint64 m_timeout;
 };
diff --git a/src/kitemviews/private/kitemlistkeyboardsearchmanager.cpp b/src/kitemviews/private/kitemlistkeyboardsearchmanager.cpp
--- a/src/kitemviews/private/kitemlistkeyboardsearchmanager.cpp
+++ b/src/kitemviews/private/kitemlistkeyboardsearchmanager.cpp
@@ -22,9 +22,9 @@
 
 #include "kitemlistkeyboardsearchmanager.h"
 
-
 KItemListKeyboardSearchManager::KItemListKeyboardSearchManager(QObject* parent) :
     QObject(parent),
+    m_isSearchRestarted(false),
     m_timeout(1000)
 {
     m_keyboardInputTime.invalidate();
@@ -34,11 +34,16 @@
 {
 }
 
-void KItemListKeyboardSearchManager::addKeys(const QString& keys)
+bool KItemListKeyboardSearchManager::shouldClearSearchIfInputTimeReached()
 {
     const bool keyboardTimeWasValid = m_keyboardInputTime.isValid();
     const qint64 keyboardInputTimeElapsed = m_keyboardInputTime.restart();
-    if (keyboardInputTimeElapsed > m_timeout || !keyboardTimeWasValid) {
+    return (keyboardInputTimeElapsed > m_timeout) || !keyboardTimeWasValid;
+}
+
+void KItemListKeyboardSearchManager::addKeys(const QString& keys)
+{
+    if (shouldClearSearchIfInputTimeReached()) {
         m_searchedString.clear();
     }
 
@@ -59,9 +64,13 @@
         const bool sameKey = m_searchedString.length() > 1 && m_searchedString.count(firstKey) == m_searchedString.length();
 
         // Searching for a matching item should start from the next item if either
-        // 1. a new search is started, or
+        // 1. a new search is started and a search has not been restarted or
         // 2. a 'repeated key' search is done.
-        const bool searchFromNextItem = newSearch || sameKey;
+        const bool searchFromNextItem = (!m_isSearchRestarted && newSearch) || sameKey;
+
+        // to remember not to searchFromNextItem if selection was deselected
+        // loosing keyboard search context basically
+        m_isSearchRestarted = false;
 
         emit changeCurrentItem(sameKey ? firstKey : m_searchedString, searchFromNextItem);
     }
@@ -80,6 +89,7 @@
 
 void KItemListKeyboardSearchManager::cancelSearch()
 {
+    m_isSearchRestarted = true;
     m_searchedString.clear();
 }
 
@@ -92,3 +102,12 @@
         cancelSearch();
     }
 }
+
+void KItemListKeyboardSearchManager::slotSelectionChanged(const KItemSet& current, const KItemSet& previous)
+{
+    if (!previous.isEmpty() && current.isEmpty() && previous.count() > 0 && current.count() == 0 && shouldClearSearchIfInputTimeReached()) {
+        // The selection has been emptied and the input time was reached.
+        // We should cancel the search and force the search restart
+        cancelSearch();
+    }
+}
diff --git a/src/tests/kitemlistcontrollertest.cpp b/src/tests/kitemlistcontrollertest.cpp
--- a/src/tests/kitemlistcontrollertest.cpp
+++ b/src/tests/kitemlistcontrollertest.cpp
@@ -326,6 +326,12 @@
                         << qMakePair(KeyPress(Qt::Key_E), ViewState(13, KItemSet() << 13))
                         << qMakePair(KeyPress(Qt::Key_Space), ViewState(14, KItemSet() << 14))
                         << qMakePair(KeyPress(Qt::Key_3), ViewState(15, KItemSet() << 15))
+                        << qMakePair(KeyPress(Qt::Key_Escape), ViewState(15, KItemSet()))
+                        << qMakePair(KeyPress(Qt::Key_E), ViewState(13, KItemSet() << 13))
+                        << qMakePair(KeyPress(Qt::Key_E), ViewState(14, KItemSet() << 14))
+                        << qMakePair(KeyPress(Qt::Key_E), ViewState(15, KItemSet() << 15))
+                        << qMakePair(KeyPress(Qt::Key_Escape), ViewState(15, KItemSet()))
+                        << qMakePair(KeyPress(Qt::Key_E), ViewState(13, KItemSet() << 13))
                         << qMakePair(KeyPress(Qt::Key_Home), ViewState(0, KItemSet() << 0))
                         << qMakePair(KeyPress(Qt::Key_Escape), ViewState(0, KItemSet()));