diff --git a/src/NotifyIconWpf/TaskbarIcon.Declarations.cs b/src/NotifyIconWpf/TaskbarIcon.Declarations.cs
index 45c8300..39bafb2 100644
--- a/src/NotifyIconWpf/TaskbarIcon.Declarations.cs
+++ b/src/NotifyIconWpf/TaskbarIcon.Declarations.cs
@@ -189,7 +189,7 @@ public Icon Icon
                 icon = value;
                 iconData.IconHandle = value == null ? IntPtr.Zero : icon.Handle;
 
-                Util.WriteIconData(ref iconData, NotifyCommand.Modify, IconDataMembers.Icon);
+                Util.WriteIconData(ref iconData, NotifyCommand.Modify, WithTrayToolTip(IconDataMembers.Icon));
             }
         }
 
diff --git a/src/NotifyIconWpf/TaskbarIcon.cs b/src/NotifyIconWpf/TaskbarIcon.cs
index f07b01d..18b4bc0 100644
--- a/src/NotifyIconWpf/TaskbarIcon.cs
+++ b/src/NotifyIconWpf/TaskbarIcon.cs
@@ -91,6 +91,11 @@ public partial class TaskbarIcon : FrameworkElement, IDisposable
         /// </summary>
         public bool SupportsCustomToolTips => messageSink.Version == NotifyIconVersion.Vista;
 
+        /// <summary>
+        /// Indicates that ToolTipText should be displayed.
+        /// </summary>
+        private bool showSystemToolTip = false;
+
 
         /// <summary>
         /// Checks whether a non-tooltip popup is currently opened.
@@ -554,14 +559,6 @@ private void CreateCustomToolTip()
                     Content = TrayToolTip
                 };
             }
-            else if (tt == null && !string.IsNullOrEmpty(ToolTipText))
-            {
-                // create a simple tooltip for the ToolTipText string
-                tt = new ToolTip
-                {
-                    Content = ToolTipText
-                };
-            }
 
             // the tooltip explicitly gets the DataContext of this instance.
             // If there is no DataContext, the TaskbarIcon assigns itself
@@ -574,6 +571,21 @@ private void CreateCustomToolTip()
             SetTrayToolTipResolved(tt);
         }
 
+        /// <summary>
+        /// Shell_NotifyIcon requires NIF_SHOWTIP to be specified for every call to Shell_NotifyIcon.
+        /// This modifies <paramref name="flags"/> to include this if required.
+        /// </summary>
+        /// <param name="flags">Passed through flags fo Shell_NotifyIcon.</param>
+        /// <returns>Flags amended with NIF_SHOWTIP if required.</returns>
+        private IconDataMembers WithTrayToolTip(IconDataMembers flags)
+        {
+            if (showSystemToolTip)
+            {
+                flags |= IconDataMembers.UseLegacyToolTips;
+            }
+
+            return flags;
+        }
 
         /// <summary>
         /// Sets tooltip settings for the class depending on defined
@@ -583,6 +595,7 @@ private void WriteToolTipSettings()
         {
             const IconDataMembers flags = IconDataMembers.Tip;
             iconData.ToolTipText = ToolTipText;
+            showSystemToolTip = TrayToolTip is null;
 
             if (messageSink.Version == NotifyIconVersion.Vista)
             {
@@ -597,7 +610,7 @@ private void WriteToolTipSettings()
             }
 
             // update the tooltip text
-            Util.WriteIconData(ref iconData, NotifyCommand.Modify, flags);
+            Util.WriteIconData(ref iconData, NotifyCommand.Modify, WithTrayToolTip(flags));
         }
 
         #endregion
@@ -871,7 +884,7 @@ private void ShowBalloonTip(string title, string message, BalloonFlags flags, In
 
             iconData.BalloonFlags = flags;
             iconData.CustomBalloonIconHandle = balloonIconHandle;
-            Util.WriteIconData(ref iconData, NotifyCommand.Modify, IconDataMembers.Info | IconDataMembers.Icon);
+            Util.WriteIconData(ref iconData, NotifyCommand.Modify, WithTrayToolTip(IconDataMembers.Info | IconDataMembers.Icon));
         }
 
 
@@ -884,7 +897,7 @@ public void HideBalloonTip()
 
             // reset balloon by just setting the info to an empty string
             iconData.BalloonText = iconData.BalloonTitle = string.Empty;
-            Util.WriteIconData(ref iconData, NotifyCommand.Modify, IconDataMembers.Info);
+            Util.WriteIconData(ref iconData, NotifyCommand.Modify, WithTrayToolTip(IconDataMembers.Info));
         }
 
         #endregion
@@ -975,7 +988,7 @@ private void CreateTaskbarIcon()
                                                 | IconDataMembers.Tip;
 
                 //write initial configuration
-                var status = Util.WriteIconData(ref iconData, NotifyCommand.Add, members);
+                var status = Util.WriteIconData(ref iconData, NotifyCommand.Add, WithTrayToolTip(members));
                 if (!status)
                 {
                     // couldn't create the icon - we can assume this is because explorer is not running (yet!)
@@ -1007,7 +1020,7 @@ private void RemoveTaskbarIcon()
                     return;
                 }
 
-                Util.WriteIconData(ref iconData, NotifyCommand.Delete, IconDataMembers.Message);
+                Util.WriteIconData(ref iconData, NotifyCommand.Delete, WithTrayToolTip(IconDataMembers.Message));
                 IsTaskbarIconCreated = false;
             }
         }