diff --git a/main.c b/main.c
index 338acc3f..007e99e4 100644
--- a/main.c
+++ b/main.c
@@ -502,7 +502,7 @@ HandleCopyDataMessage(const COPYDATASTRUCT *copy_data)
     }
     else if (copy_data->dwData == WM_OVPN_RESCAN)
     {
-        OnNotifyTray(WM_OVPN_RESCAN);
+        OnNotifyTray(0, WM_OVPN_RESCAN);
     }
     else
     {
@@ -641,7 +641,7 @@ WindowProcedure(HWND hwnd, UINT message, WPARAM wParam, LPARAM lParam)
             break;
 
         case WM_NOTIFYICONTRAY:
-            OnNotifyTray(lParam); /* Manages message from tray */
+            OnNotifyTray(wParam, lParam); /* Manages message from tray */
             break;
 
         case WM_COPYDATA: /* custom messages with data from other processes */
diff --git a/tray.c b/tray.c
index a5e48900..a9c47e4f 100644
--- a/tray.c
+++ b/tray.c
@@ -28,6 +28,7 @@
 #include <shellapi.h>
 #include <tchar.h>
 #include <time.h>
+#include <commctrl.h>
 
 #include "tray.h"
 #include "main.h"
@@ -47,6 +48,9 @@ int hmenu_size = 0; /* allocated size of hMenuConn array */
 HBITMAP hbmpConnecting;
 
 NOTIFYICONDATA ni;
+HWND traytip; /* handle of tooltip window for tray icon */
+TOOLINFO ti;  /* global tool info structure for tool tip of tray icon*/
+
 extern options_t o;
 
 #define USE_NESTED_CONFIG_MENU ((o.config_menu_view == CONFIG_VIEW_AUTO && o.num_configs > 25)   \
@@ -351,15 +355,43 @@ RecreatePopupMenus(void)
     CreatePopupMenus();
 }
 
+/*
+ * Position tool tip window so that it does not overlap with the mouse position
+ * and does not spill out of the screen. If mouse location overlaps, NIM_POPUPCLOSE
+ * and NIM_POPUPOPEN will trigger continuously.
+ * Account for the possibility that the taskbar could be at the bottom, right, top
+ * or left edge of the screen.
+ *
+ * On input (x, y) is the mouse position that triggered the display of tooltip
+ */
+static void
+PositionTrayToolTip(LONG x, LONG y)
+{
+    RECT r;
+    LONG cxmax = GetSystemMetrics(SM_CXSCREEN);
+    GetWindowRect(traytip, &r);
+    LONG w = r.right - r.left;
+    LONG h = r.bottom - r.top;
+    /* - vertically, position the bottom of the window 10 pixels above y or top of the window
+     *   10 pixels below y depending on whether we are closer to the bottom or top of the screen.
+     * - horizontally, try to centre around x adjusting for overflow to the right or left
+     */
+    r.left = (x < w/2) ? 0 : ((x + w/2 < cxmax) ? x - w/2 : cxmax - w);
+    r.top = (y > h + 10) ?  y - (h + 10) : y + 10;
+    SendMessageW(traytip, TTM_TRACKPOSITION, 0, MAKELONG(r.left, r.top));
+    SetWindowPos(traytip, HWND_TOPMOST, 0, 0, 0, 0, SWP_NOSIZE|SWP_NOMOVE);
+}
+
 /*
  * Handle mouse clicks on tray icon
  */
 void
-OnNotifyTray(LPARAM lParam)
+OnNotifyTray(WPARAM wParam, LPARAM lParam)
 {
     POINT pt;
 
-    switch (lParam)
+    /* Use LOWORD(lParam)  as HIWORD() contains the icon id if uVersion >= 4 */
+    switch (LOWORD(lParam))
     {
         case WM_RBUTTONUP:
             RecreatePopupMenus();
@@ -401,6 +433,22 @@ OnNotifyTray(LPARAM lParam)
         }
         break;
 
+        /* handle messages when mouse enters and leaves the icon -- we show the custom tooltip window */
+        case NIN_POPUPOPEN:
+            if (traytip)
+            {
+                SendMessageW(traytip, TTM_TRACKACTIVATE, (WPARAM)TRUE, (LPARAM) &ti);
+                PositionTrayToolTip(LOWORD(wParam), HIWORD(wParam)); /* wParam has mouse position */
+            }
+            break;
+
+        case NIN_POPUPCLOSE:
+            if (traytip)
+            {
+                SendMessageW(traytip, TTM_TRACKACTIVATE, (WPARAM)FALSE, 0);
+            }
+            break;
+
         case WM_OVPN_RESCAN:
             /* Rescan config folders and recreate popup menus */
             RecreatePopupMenus();
@@ -416,6 +464,11 @@ RemoveTrayIcon()
         Shell_NotifyIcon(NIM_DELETE, &ni);
         CLEAR(ni);
     }
+    if (traytip)
+    {
+        DestroyWindow(traytip);
+        traytip = NULL;
+    }
 }
 
 void
@@ -435,21 +488,48 @@ ShowTrayIcon()
     ni.uCallbackMessage = WM_NOTIFYICONTRAY;
     ni.hIcon = LoadLocalizedSmallIcon(ID_ICO_DISCONNECTED);
     _tcsncpy(ni.szTip, _T(PACKAGE_NAME), _countof(_T(PACKAGE_NAME)));
+    ni.uVersion = NOTIFYICON_VERSION_4;
 
     Shell_NotifyIcon(NIM_ADD, &ni);
+
+    /* try to set version 4 and a custom tooltip window */
+    if (Shell_NotifyIcon(NIM_SETVERSION, &ni))
+    {
+        /* create a custom tooltip for the tray */
+        traytip = CreateWindowEx(0, TOOLTIPS_CLASS, NULL, WS_POPUP |TTS_ALWAYSTIP,
+                                 CW_USEDEFAULT, CW_USEDEFAULT, CW_USEDEFAULT, CW_USEDEFAULT,
+                                 o.hWnd, NULL, o.hInstance, NULL);
+        if (!traytip) /* revert the version back so that we can use legacy ni.szTip for tip text */
+        {
+            ni.uVersion = 0;
+            Shell_NotifyIcon(NIM_SETVERSION, &ni);
+        }
+    }
+
+    if (traytip)
+    {
+        LONG cx = GetSystemMetrics(SM_CXSCREEN)/4; /* max width of tray tooltip = 25% of screen */
+        ti.cbSize = sizeof(ti);
+        ti.uId = (UINT_PTR) traytip;
+        ti.uFlags = TTF_ABSOLUTE|TTF_TRACK|TTF_IDISHWND;
+        ti.hwnd = o.hWnd;
+        ti.lpszText = L"";
+        SendMessage(traytip, TTM_ADDTOOL, 0, (LPARAM)&ti);
+        SendMessage(traytip, TTM_SETTITLE, TTI_NONE, (LPARAM) _T(PACKAGE_NAME));
+        SendMessage(traytip, TTM_SETMAXTIPWIDTH, 0, (LPARAM) cx);
+    }
 }
 
 void
 SetTrayIcon(conn_state_t state)
 {
-    TCHAR msg[500];
+    TCHAR msg[500] = L"";
     TCHAR msg_connected[100];
     TCHAR msg_connecting[100];
     BOOL first_conn;
     UINT icon_id;
     connection_t *cc = NULL; /* a connected config */
 
-    _tcsncpy(msg, _T(PACKAGE_NAME), _countof(_T(PACKAGE_NAME)));
     _tcsncpy(msg_connected, LoadLocalizedString(IDS_TIP_CONNECTED), _countof(msg_connected));
     _tcsncpy(msg_connecting, LoadLocalizedString(IDS_TIP_CONNECTING), _countof(msg_connecting));
 
@@ -482,13 +562,23 @@ SetTrayIcon(conn_state_t state)
     {
         /* Append "Connected since and assigned IP" to message */
         TCHAR time[50];
+        WCHAR ip[64];
+
+        /* If there is not enough space in the message to add time and IP, truncate it.
+         * This works only if custom tooltip window is in use.
+         * Include about 50 characters for "Connected since:" and "Assigned IP:" prefixes.
+         */
+        size_t max_msglen = _countof(msg) - (_countof(time) + _countof(ip) + 50);
+        if (_tcslen(msg)  > max_msglen && traytip)
+        {
+            wcsncpy(&msg[max_msglen-1], L"…", 1);
+        }
 
         LocalizedTime(cc->connected_since, time, _countof(time));
         _tcsncat(msg, LoadLocalizedString(IDS_TIP_CONNECTED_SINCE), _countof(msg) - _tcslen(msg) - 1);
         _tcsncat(msg, time, _countof(msg) - _tcslen(msg) - 1);
 
         /* concatenate ipv4 and ipv6 addresses into one string */
-        WCHAR ip[64];
         wcs_concat2(ip, _countof(ip), cc->ip, cc->ipv6, L", ");
         WCHAR *assigned_ip = LoadLocalizedString(IDS_TIP_ASSIGNED_IP, ip);
         _tcsncat(msg, assigned_ip, _countof(msg) - _tcslen(msg) - 1);
@@ -508,9 +598,23 @@ SetTrayIcon(conn_state_t state)
     ni.uID = 0;
     ni.hWnd = o.hWnd;
     ni.hIcon = LoadLocalizedSmallIcon(icon_id);
-    ni.uFlags = NIF_MESSAGE | NIF_TIP | NIF_ICON;
+    ni.uFlags = NIF_MESSAGE | NIF_ICON;
     ni.uCallbackMessage = WM_NOTIFYICONTRAY;
-    _tcsncpy(ni.szTip, msg, _countof(ni.szTip));
+
+    if (traytip)
+    {
+        /* Set msg as the tool tip text -- skip the leading "\n" */
+        WCHAR *msgp = msg;
+        msgp += (msgp[0] == L'\n') ? 1 : 0;
+        /* tool tip window needs a non-empty text to show */
+        ti.lpszText = wcslen(msgp) ? msgp : L" ";
+        SendMessage(traytip, TTM_UPDATETIPTEXT, 0, (LPARAM) &ti);
+    }
+    else
+    {
+        _sntprintf_0(ni.szTip, L"%ls%ls", _T(PACKAGE_NAME), msg);
+        ni.uFlags |= NIF_TIP;
+    }
 
     Shell_NotifyIcon(NIM_MODIFY, &ni);
 }
diff --git a/tray.h b/tray.h
index 199d3c39..2cbfa66f 100644
--- a/tray.h
+++ b/tray.h
@@ -49,7 +49,7 @@ void RecreatePopupMenus(void);
 
 void CreatePopupMenus();
 
-void OnNotifyTray(LPARAM);
+void OnNotifyTray(WPARAM, LPARAM);
 
 void OnDestroyTray(void);