diff --git a/CHANGELOG.md b/CHANGELOG.md
index 5c237ef8..1fc81f52 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -23,6 +23,8 @@ FlatLaf Change Log
   as row header in scroll pane. (issues #152 and #46)
 - TableHeader: Fixed position of column separators in right-to-left component
   orientation.
+- ToolTip: Fixed drop shadow for wide tooltips on Windows and Java 9+. (issue
+  #224)
 - SwingX: Fixed striping background highlighting color (e.g. alternating table
   rows) in dark themes.
 
diff --git a/flatlaf-core/src/main/java/com/formdev/flatlaf/ui/FlatPopupFactory.java b/flatlaf-core/src/main/java/com/formdev/flatlaf/ui/FlatPopupFactory.java
index b04a744c..45199226 100644
--- a/flatlaf-core/src/main/java/com/formdev/flatlaf/ui/FlatPopupFactory.java
+++ b/flatlaf-core/src/main/java/com/formdev/flatlaf/ui/FlatPopupFactory.java
@@ -271,16 +271,17 @@ public class FlatPopupFactory
 
 				// increase tooltip size if necessary because it may be too small on HiDPI screens
 				//    https://bugs.openjdk.java.net/browse/JDK-8213535
-				if( contents instanceof JToolTip ) {
+				if( contents instanceof JToolTip && popupWindow == null ) {
 					Container parent = contents.getParent();
 					if( parent instanceof JPanel ) {
 						Dimension prefSize = parent.getPreferredSize();
 						if( !prefSize.equals( parent.getSize() ) ) {
-							Container panel = SwingUtilities.getAncestorOfClass( Panel.class, parent );
-							if( panel != null )
-								panel.setSize( prefSize ); // for medium weight popup
-							else
-								parent.setSize( prefSize ); // for light weight popup
+							Container mediumWeightPanel = SwingUtilities.getAncestorOfClass( Panel.class, parent );
+							Container c = (mediumWeightPanel != null)
+								? mediumWeightPanel // medium weight popup
+								: parent;           // light weight popup
+							c.setSize( prefSize );
+							c.validate();
 						}
 					}
 				}
diff --git a/flatlaf-testing/src/main/java/com/formdev/flatlaf/testing/FlatComponentsTest.java b/flatlaf-testing/src/main/java/com/formdev/flatlaf/testing/FlatComponentsTest.java
index e696fa17..5cee1105 100644
--- a/flatlaf-testing/src/main/java/com/formdev/flatlaf/testing/FlatComponentsTest.java
+++ b/flatlaf-testing/src/main/java/com/formdev/flatlaf/testing/FlatComponentsTest.java
@@ -487,6 +487,7 @@ public class FlatComponentsTest
 
 		//---- toggleButton1 ----
 		toggleButton1.setText("Enabled");
+		toggleButton1.setToolTipText("LOOOOOOOOOOOOOONG TEXT");
 		add(toggleButton1, "cell 1 2");
 
 		//---- toggleButton9 ----
diff --git a/flatlaf-testing/src/main/java/com/formdev/flatlaf/testing/FlatComponentsTest.jfd b/flatlaf-testing/src/main/java/com/formdev/flatlaf/testing/FlatComponentsTest.jfd
index 1e87e0b5..a7981e66 100644
--- a/flatlaf-testing/src/main/java/com/formdev/flatlaf/testing/FlatComponentsTest.jfd
+++ b/flatlaf-testing/src/main/java/com/formdev/flatlaf/testing/FlatComponentsTest.jfd
@@ -159,6 +159,7 @@ new FormModel {
 			add( new FormComponent( "javax.swing.JToggleButton" ) {
 				name: "toggleButton1"
 				"text": "Enabled"
+				"toolTipText": "LOOOOOOOOOOOOOONG TEXT"
 			}, new FormLayoutConstraints( class net.miginfocom.layout.CC ) {
 				"value": "cell 1 2"
 			} )