diff --git a/krita/main.cc b/krita/main.cc
--- a/krita/main.cc
+++ b/krita/main.cc
@@ -55,6 +55,7 @@
 #include <kis_tablet_support_win8.h>
 #include <kis_config.h>
 #include <QLibrary>
+#include <QMessageBox>
 
 #elif defined HAVE_X11
 #include <kis_xi2_event_filter.h>
@@ -321,23 +322,42 @@
 #if defined Q_OS_WIN
     {
         KisConfig cfg;
-        bool isUsingWin8PointerInput = false;
+        if (cfg.useWin8PointerInput() && !KisTabletSupportWin8::isAvailable()) {
+            cfg.setUseWin8PointerInput(false);
+        }
+        if (!cfg.useWin8PointerInput()) {
+            bool hasWinTab = KisTabletSupportWin::init();
+            if (!hasWinTab) {
+                if (KisTabletSupportWin8::isPenDeviceAvailable()) {
+                    // Use WinInk automatically
+                    cfg.setUseWin8PointerInput(true);
+                } else if (!cfg.readEntry("WarnedAboutMissingWinTab", false)) {
+                    if (KisTabletSupportWin8::isAvailable()) {
+                        QMessageBox::information(nullptr,
+                                i18n("Krita Tablet Support"),
+                                i18n("Cannot load WinTab driver and no Windows Ink pen devices are found. If you have a drawing tablet, please make sure the tablet driver is properly installed."),
+                                QMessageBox::Ok, QMessageBox::Ok);
+                    } else {
+                        QMessageBox::information(nullptr,
+                                i18n("Krita Tablet Support"),
+                                i18n("Cannot load WinTab driver. If you have a drawing tablet, please make sure the tablet driver is properly installed."),
+                                QMessageBox::Ok, QMessageBox::Ok);
+                    }
+                    cfg.writeEntry("WarnedAboutMissingWinTab", true);
+                }
+            }
+        }
         if (cfg.useWin8PointerInput()) {
             KisTabletSupportWin8 *penFilter = new KisTabletSupportWin8();
             if (penFilter->init()) {
                 // penFilter.registerPointerDeviceNotifications();
                 app.installNativeEventFilter(penFilter);
-                isUsingWin8PointerInput = true;
                 qDebug() << "Using Win8 Pointer Input for tablet support";
             } else {
                 qDebug() << "No Win8 Pointer Input available";
                 delete penFilter;
             }
         }
-        if (!isUsingWin8PointerInput) {
-            KisTabletSupportWin::init();
-            // app.installNativeEventFilter(new KisTabletSupportWin());
-        }
     }
 #endif
 
@@ -365,4 +385,3 @@
 
     return state;
 }
-
diff --git a/libs/ui/input/wintab/kis_tablet_support_win.h b/libs/ui/input/wintab/kis_tablet_support_win.h
--- a/libs/ui/input/wintab/kis_tablet_support_win.h
+++ b/libs/ui/input/wintab/kis_tablet_support_win.h
@@ -26,7 +26,7 @@
 class KRITAUI_EXPORT KisTabletSupportWin
 {
 public:
-    static void init();
+    static bool init();
 
 };
 
diff --git a/libs/ui/input/wintab/kis_tablet_support_win.cpp b/libs/ui/input/wintab/kis_tablet_support_win.cpp
--- a/libs/ui/input/wintab/kis_tablet_support_win.cpp
+++ b/libs/ui/input/wintab/kis_tablet_support_win.cpp
@@ -162,11 +162,11 @@
 
 QWindowsWinTab32DLL QWindowsTabletSupport::m_winTab32DLL;
 
-void KisTabletSupportWin::init()
+bool KisTabletSupportWin::init()
 {
     if (!QWindowsTabletSupport::m_winTab32DLL.init()) {
         qWarning() << "Failed to initialize Wintab";
-        return;
+        return false;
     }
 
     QTAB = QWindowsTabletSupport::create();
@@ -177,6 +177,7 @@
                          delete QTAB;
                          QTAB = QWindowsTabletSupport::create();
                      });
+    return true;
 }
 
 
diff --git a/libs/ui/input/wintab/kis_tablet_support_win8.h b/libs/ui/input/wintab/kis_tablet_support_win8.h
--- a/libs/ui/input/wintab/kis_tablet_support_win8.h
+++ b/libs/ui/input/wintab/kis_tablet_support_win8.h
@@ -29,6 +29,7 @@
 
 public:
     static bool isAvailable();
+    static bool isPenDeviceAvailable();
 
     KisTabletSupportWin8() = default;
     ~KisTabletSupportWin8() = default;
diff --git a/libs/ui/input/wintab/kis_tablet_support_win8.cpp b/libs/ui/input/wintab/kis_tablet_support_win8.cpp
--- a/libs/ui/input/wintab/kis_tablet_support_win8.cpp
+++ b/libs/ui/input/wintab/kis_tablet_support_win8.cpp
@@ -60,7 +60,7 @@
     FUNC(GetPointerPenInfoHistory) \
     FUNC(GetPointerType) \
     /* Pointer Device Functions */ \
-    /*FUNC(GetPointerDevices)*/ \
+    FUNC(GetPointerDevices) \
     /*FUNC(GetPointerDeviceProperties)*/ \
     FUNC(GetPointerDevice) \
     FUNC(GetPointerDeviceRects) \
@@ -340,6 +340,39 @@
     return api.init();
 }
 
+bool KisTabletSupportWin8::isPenDeviceAvailable()
+{
+    if (!api.init()) {
+        return false;
+    }
+    UINT32 deviceCount = 0;
+    if (!api.GetPointerDevices(&deviceCount, nullptr)) {
+        dbgTablet << "GetPointerDevices failed";
+        return false;
+    }
+    if (deviceCount == 0) {
+        dbgTablet << "No pointer devices";
+        return false;
+    }
+    QVector<POINTER_DEVICE_INFO> devices(deviceCount);
+    if (!api.GetPointerDevices(&deviceCount, devices.data())) {
+        dbgTablet << "GetPointerDevices failed";
+        return false;
+    }
+    bool hasPenDevice = false;
+    Q_FOREACH (const POINTER_DEVICE_INFO &device, devices) {
+        dbgTablet << "Found pointer device" << static_cast<void *>(device.device)
+                  << QString::fromWCharArray(device.productString)
+                  << "type:" << device.pointerDeviceType;
+        if (device.pointerDeviceType == POINTER_DEVICE_TYPE_INTEGRATED_PEN ||
+            device.pointerDeviceType == POINTER_DEVICE_TYPE_EXTERNAL_PEN) {
+            hasPenDevice = true;
+        }
+    }
+    dbgTablet << "hasPenDevice:" << hasPenDevice;
+    return hasPenDevice;
+}
+
 bool KisTabletSupportWin8::init()
 {
     return api.init();