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>
@@ -323,23 +324,42 @@
 #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 && !cfg.readEntry("WarnedAboutMissingWinTab", false)) {
+                if (KisTabletSupportWin8::isAvailable()) {
+                    QMessageBox::StandardButton mboxResult = QMessageBox::question(nullptr,
+                            i18n("Krita Tablet Support"),
+                            i18n("Cannot load WinTab driver. If you have a drawing tablet, please make sure the driver is properly installed.\n\n"
+                                  "Alternatively, if your tablet supports Windows Ink, it can be used instead of WinTab. Windows Ink is recommended for Microsoft Surface devices.\n\n"
+                                  "Change to use Windows Ink now? (This option can be changed later.)"),
+                            QMessageBox::Yes | QMessageBox::No, QMessageBox::Yes);
+                    if (mboxResult == QMessageBox::Yes) {
+                        cfg.setUseWin8PointerInput(true);
+                    }
+                } else {
+                    QMessageBox::information(nullptr,
+                            i18n("Krita Tablet Support"),
+                            i18n("Cannot load WinTab driver. If you have a drawing tablet, please make sure the 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
 
@@ -367,4 +387,3 @@
 
     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;
 }