diff --git a/intern/ghost/intern/GHOST_SystemWin32.cpp b/intern/ghost/intern/GHOST_SystemWin32.cpp
index 181e3ad4014..5de97199fd8 100644
--- a/intern/ghost/intern/GHOST_SystemWin32.cpp
+++ b/intern/ghost/intern/GHOST_SystemWin32.cpp
@@ -1559,7 +1559,12 @@ LRESULT WINAPI GHOST_SystemWin32::s_wndProc(HWND hwnd, UINT msg, WPARAM wParam,
           break;
         case WT_PROXIMITY: {
           if (window->useTabletAPI(GHOST_kTabletWintab)) {
-            window->m_tabletInRange = LOWORD(lParam);
+            if (LOWORD(lParam)) {
+              window->m_tabletInRange = true;
+            }
+            else {
+              window->processWintabLeave();
+            }
           }
           eventHandled = true;
           break;
diff --git a/intern/ghost/intern/GHOST_WindowWin32.cpp b/intern/ghost/intern/GHOST_WindowWin32.cpp
index f5088c6505e..255d487649b 100644
--- a/intern/ghost/intern/GHOST_WindowWin32.cpp
+++ b/intern/ghost/intern/GHOST_WindowWin32.cpp
@@ -1155,16 +1155,21 @@ void GHOST_WindowWin32::setWintabOverlap(bool overlap)
         /* If context is disabled, Windows Ink may be active and managing m_tabletInRange. Don't
          * modify it. */
         if (!(context.lcStatus & CXS_DISABLED)) {
-          /* Set tablet as not in range, proximity event may not occur. */
-          m_tabletInRange = false;
-          /* Clear the packet queue. */
-          m_wintab.packetsGet(m_wintab.context, m_wintab.pkts.size(), m_wintab.pkts.data());
+          processWintabLeave();
         }
       }
     }
   }
 }
 
+void GHOST_WindowWin32::processWintabLeave()
+{
+  m_tabletInRange = false;
+  m_wintab.buttons = 0;
+  /* Clear the packet queue. */
+  m_wintab.packetsGet(m_wintab.context, m_wintab.pkts.size(), m_wintab.pkts.data());
+}
+
 void GHOST_WindowWin32::processWintabDisplayChangeEvent()
 {
   LOGCONTEXT lc_sys = {0}, lc_curr = {0};
@@ -1327,17 +1332,32 @@ GHOST_TSuccess GHOST_WindowWin32::getWintabInfo(std::vector<GHOST_WintabInfoWin3
       out.tabletData.Ytilt = (float)(sin(M_PI / 2.0 - azmRad) * vecLen);
     }
 
-    out.button = wintabMouseToGhost(pkt.pkCursor, LOWORD(pkt.pkButtons));
-    switch (HIWORD(pkt.pkButtons)) {
-      case TBN_NONE:
-        out.type = GHOST_kEventCursorMove;
-        break;
-      case TBN_DOWN:
-        out.type = GHOST_kEventButtonDown;
-        break;
-      case TBN_UP:
-        out.type = GHOST_kEventButtonUp;
-        break;
+    /* Some Wintab libraries don't handle relative button input, so we track button presses
+     * manually. */
+    out.button = GHOST_kButtonMaskNone;
+    out.type = GHOST_kEventCursorMove;
+
+    DWORD buttonsChanged = m_wintab.buttons ^ pkt.pkButtons;
+    if (buttonsChanged) {
+      /* Find the index for the changed button from the button map. */
+      WORD physicalButton = 0;
+      for (DWORD diff = (unsigned)buttonsChanged >> 1; diff > 0; diff = (unsigned)diff >> 1) {
+        physicalButton++;
+      }
+
+      out.button = wintabMouseToGhost(pkt.pkCursor, physicalButton);
+
+      if (out.button != GHOST_kButtonMaskNone) {
+        if (buttonsChanged & pkt.pkButtons) {
+          out.type = GHOST_kEventButtonDown;
+        }
+        else {
+          out.type = GHOST_kEventButtonUp;
+        }
+      }
+
+      /* Only update handled button, in case multiple button events arrived simultaneously. */
+      m_wintab.buttons ^= 1 << physicalButton;
     }
 
     out.time = system->tickCountToMillis(pkt.pkTime);
diff --git a/intern/ghost/intern/GHOST_WindowWin32.h b/intern/ghost/intern/GHOST_WindowWin32.h
index 1cff8b2036e..a7e7cdc6602 100644
--- a/intern/ghost/intern/GHOST_WindowWin32.h
+++ b/intern/ghost/intern/GHOST_WindowWin32.h
@@ -41,7 +41,7 @@
 // PACKETDATA and PACKETMODE modify structs in pktdef.h, so make sure they come first
 #define PACKETDATA \
   (PK_BUTTONS | PK_NORMAL_PRESSURE | PK_ORIENTATION | PK_CURSOR | PK_X | PK_Y | PK_TIME)
-#define PACKETMODE PK_BUTTONS
+#define PACKETMODE 0
 #include <pktdef.h>
 
 class GHOST_SystemWin32;
@@ -466,6 +466,11 @@ class GHOST_WindowWin32 : public GHOST_Window {
    */
   void setWintabOverlap(bool overlap);
 
+  /**
+   * Resets Wintab state.
+   */
+  void processWintabLeave();
+
   /**
    * Handle Wintab coordinate changes when DisplayChange events occur.
    */
@@ -614,6 +619,8 @@ class GHOST_WindowWin32 : public GHOST_Window {
     HCTX context = NULL;
     /** Number of connected Wintab digitizers. */
     UINT numDevices = 0;
+    /** Pressed button map. */
+    GHOST_TUns8 buttons = 0;
     LONG maxPressure = 0;
     LONG maxAzimuth = 0, maxAltitude = 0;
     /** Reusable buffer to read in Wintab Packets. */