diff --git a/CHANGELOG.md b/CHANGELOG.md
index b2191fc4..87de3294 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,6 +1,12 @@
 FlatLaf Change Log
 ==================
 
+## 1.5-SNAPSHOT
+
+- Popup: Fixed incorrectly placed drop shadow for medium-weight popups in
+  maximized windows. (issue #358)
+
+
 ## 1.4
 
 #### New features and improvements
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 374e5e6a..94c65fa9 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
@@ -489,6 +489,9 @@ public class FlatPopupFactory
 			JLayeredPane layeredPane = ((RootPaneContainer)window).getLayeredPane();
 			layeredPane.add( dropShadowPanel, JLayeredPane.POPUP_LAYER, 0 );
 
+			moveMediumWeightDropShadow();
+			resizeMediumWeightDropShadow();
+
 			mediumPanelListener = new ComponentListener() {
 				@Override
 				public void componentShown( ComponentEvent e ) {
@@ -504,17 +507,12 @@ public class FlatPopupFactory
 
 				@Override
 				public void componentMoved( ComponentEvent e ) {
-					if( dropShadowPanel != null && mediumWeightPanel != null ) {
-						Point location = mediumWeightPanel.getLocation();
-						Insets insets = dropShadowPanel.getInsets();
-						dropShadowPanel.setLocation( location.x - insets.left, location.y - insets.top );
-					}
+					moveMediumWeightDropShadow();
 				}
 
 				@Override
 				public void componentResized( ComponentEvent e ) {
-					if( dropShadowPanel != null )
-						dropShadowPanel.setSize( FlatUIUtils.addInsets( mediumWeightPanel.getSize(), dropShadowPanel.getInsets() ) );
+					resizeMediumWeightDropShadow();
 				}
 			};
 			mediumWeightPanel.addComponentListener( mediumPanelListener );
@@ -530,5 +528,18 @@ public class FlatPopupFactory
 				parent.repaint( bounds.x, bounds.y, bounds.width, bounds.height );
 			}
 		}
+
+		private void moveMediumWeightDropShadow() {
+			if( dropShadowPanel != null && mediumWeightPanel != null ) {
+				Point location = mediumWeightPanel.getLocation();
+				Insets insets = dropShadowPanel.getInsets();
+				dropShadowPanel.setLocation( location.x - insets.left, location.y - insets.top );
+			}
+		}
+
+		private void resizeMediumWeightDropShadow() {
+			if( dropShadowPanel != null && mediumWeightPanel != null )
+				dropShadowPanel.setSize( FlatUIUtils.addInsets( mediumWeightPanel.getSize(), dropShadowPanel.getInsets() ) );
+		}
 	}
 }
diff --git a/flatlaf-testing/src/main/java/com/formdev/flatlaf/testing/FlatPopupTest.java b/flatlaf-testing/src/main/java/com/formdev/flatlaf/testing/FlatPopupTest.java
new file mode 100644
index 00000000..05788bc9
--- /dev/null
+++ b/flatlaf-testing/src/main/java/com/formdev/flatlaf/testing/FlatPopupTest.java
@@ -0,0 +1,361 @@
+/*
+ * Copyright 2021 FormDev Software GmbH
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ *
+ *     https://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+package com.formdev.flatlaf.testing;
+
+import java.awt.*;
+import java.awt.Point;
+import javax.swing.*;
+import com.formdev.flatlaf.util.Animator;
+import net.miginfocom.swing.*;
+
+/**
+ * @author Karl Tauber
+ */
+public class FlatPopupTest
+	extends FlatTestPanel
+{
+	private Popup popup;
+
+	public static void main( String[] args ) {
+		SwingUtilities.invokeLater( () -> {
+			FlatTestFrame frame = FlatTestFrame.create( args, "FlatPopupTest" );
+			frame.showFrame( FlatPopupTest::new );
+		} );
+	}
+
+	FlatPopupTest() {
+		initComponents();
+	}
+
+	private void showPopupMenu() {
+		popupMenu1.show( showPopupMenuButton, 0, showPopupMenuButton.getHeight() );
+	}
+
+	private void showLargePopupMenu() {
+		popupMenu2.show( showLargePopupMenuButton, 0, showLargePopupMenuButton.getHeight() );
+	}
+
+	private void showPopup() {
+		showPopup( 0, 0 );
+	}
+
+	private void showPopup( int xoffset, int yoffset ) {
+		hidePopup();
+
+		Point pt = showPopupButton.getLocationOnScreen();
+		popup = PopupFactory.getSharedInstance().getPopup( showPopupButton, popupPanel,
+			pt.x + xoffset, pt.y + showPopupButton.getHeight() + yoffset );
+		popup.show();
+	}
+
+	private void hidePopup() {
+		if( popup == null )
+			return;
+
+		popup.hide();
+		popup = null;
+	}
+
+	private void movePopupDown() {
+		movePopup( 0, 600 );
+	}
+
+	private void movePopupRight() {
+		movePopup( 600, 0 );
+	}
+
+	private void movePopup( int xoffset, int yoffset ) {
+		showPopup();
+
+		Animator animator = new Animator( 1000, fraction -> {
+			System.out.println(fraction);
+			showPopup( (int) (fraction * xoffset), (int) (fraction * yoffset) );
+		} );
+		animator.start();
+	}
+
+	private void initComponents() {
+		// JFormDesigner - Component initialization - DO NOT MODIFY  //GEN-BEGIN:initComponents
+		label1 = new JLabel();
+		label2 = new JLabel();
+		showPopupMenuButton = new JButton();
+		showLargePopupMenuButton = new JButton();
+		showPopupButton = new JButton();
+		hidePopupButton = new JButton();
+		movePopupDownButton = new JButton();
+		movePopuprightButton = new JButton();
+		label4 = new JLabel();
+		popupMenu1 = new JPopupMenu();
+		menuItem1 = new JMenuItem();
+		menuItem2 = new JMenuItem();
+		menu1 = new JMenu();
+		menuItem3 = new JMenuItem();
+		menuItem4 = new JMenuItem();
+		popupPanel = new JPanel();
+		label3 = new JLabel();
+		popupMenu2 = new JPopupMenu();
+		menuItem5 = new JMenuItem();
+		menuItem6 = new JMenuItem();
+		menuItem7 = new JMenuItem();
+		menuItem8 = new JMenuItem();
+		menuItem9 = new JMenuItem();
+		menuItem10 = new JMenuItem();
+		menuItem11 = new JMenuItem();
+		menuItem12 = new JMenuItem();
+		menuItem13 = new JMenuItem();
+		menuItem14 = new JMenuItem();
+		menuItem15 = new JMenuItem();
+		menuItem16 = new JMenuItem();
+		menuItem17 = new JMenuItem();
+		menuItem18 = new JMenuItem();
+		menuItem19 = new JMenuItem();
+		menuItem20 = new JMenuItem();
+		menuItem21 = new JMenuItem();
+		menu2 = new JMenu();
+		menuItem22 = new JMenuItem();
+		menuItem23 = new JMenuItem();
+
+		//======== this ========
+		setLayout(new MigLayout(
+			"ltr,insets dialog,hidemode 3",
+			// columns
+			"[fill]" +
+			"[fill]" +
+			"[fill]" +
+			"[fill]",
+			// rows
+			"[]" +
+			"[]" +
+			"[]" +
+			"[]" +
+			"[]" +
+			"[]"));
+
+		//---- label1 ----
+		label1.setText("Label with light-weight tooltip");
+		label1.setToolTipText("some tip");
+		add(label1, "cell 0 0");
+
+		//---- label2 ----
+		label2.setText("Label with heavy-weight tooltip");
+		label2.setToolTipText("some tip\n1\n2\n3\n4\n5\n6\n7\n8\n9\n10\n11\n12\n13\n14\n15\n16\n17\n18\n19\n20\n21\n22\n23\n24\n25");
+		add(label2, "cell 0 1");
+
+		//---- showPopupMenuButton ----
+		showPopupMenuButton.setText("show light-weight JPopupMenu");
+		showPopupMenuButton.addActionListener(e -> showPopupMenu());
+		add(showPopupMenuButton, "cell 0 2");
+
+		//---- showLargePopupMenuButton ----
+		showLargePopupMenuButton.setText("show heavy-weight JPopupMenu");
+		showLargePopupMenuButton.addActionListener(e -> showLargePopupMenu());
+		add(showLargePopupMenuButton, "cell 0 3");
+
+		//---- showPopupButton ----
+		showPopupButton.setText("show medium-weight popup");
+		showPopupButton.addActionListener(e -> showPopup());
+		add(showPopupButton, "cell 0 4");
+
+		//---- hidePopupButton ----
+		hidePopupButton.setText("hide");
+		hidePopupButton.addActionListener(e -> hidePopup());
+		add(hidePopupButton, "cell 1 4");
+
+		//---- movePopupDownButton ----
+		movePopupDownButton.setText("move down");
+		movePopupDownButton.addActionListener(e -> movePopupDown());
+		add(movePopupDownButton, "cell 2 4");
+
+		//---- movePopuprightButton ----
+		movePopuprightButton.setText("move right");
+		movePopuprightButton.addActionListener(e -> movePopupRight());
+		add(movePopuprightButton, "cell 3 4");
+
+		//---- label4 ----
+		label4.setText("(switches to heavy-weight when moving outside of window)");
+		add(label4, "cell 0 5 4 1,alignx right,growx 0");
+
+		//======== popupMenu1 ========
+		{
+
+			//---- menuItem1 ----
+			menuItem1.setText("text");
+			popupMenu1.add(menuItem1);
+
+			//---- menuItem2 ----
+			menuItem2.setText("text");
+			popupMenu1.add(menuItem2);
+
+			//======== menu1 ========
+			{
+				menu1.setText("text");
+
+				//---- menuItem3 ----
+				menuItem3.setText("text");
+				menu1.add(menuItem3);
+
+				//---- menuItem4 ----
+				menuItem4.setText("text");
+				menu1.add(menuItem4);
+			}
+			popupMenu1.add(menu1);
+		}
+
+		//======== popupPanel ========
+		{
+			popupPanel.setBackground(new Color(153, 255, 153));
+			popupPanel.setLayout(new MigLayout(
+				"hidemode 3",
+				// columns
+				"[fill]",
+				// rows
+				"[]"));
+
+			//---- label3 ----
+			label3.setText("popup");
+			popupPanel.add(label3, "cell 0 0");
+		}
+
+		//======== popupMenu2 ========
+		{
+
+			//---- menuItem5 ----
+			menuItem5.setText("text");
+			popupMenu2.add(menuItem5);
+
+			//---- menuItem6 ----
+			menuItem6.setText("text");
+			popupMenu2.add(menuItem6);
+
+			//---- menuItem7 ----
+			menuItem7.setText("text");
+			popupMenu2.add(menuItem7);
+
+			//---- menuItem8 ----
+			menuItem8.setText("text");
+			popupMenu2.add(menuItem8);
+
+			//---- menuItem9 ----
+			menuItem9.setText("text");
+			popupMenu2.add(menuItem9);
+
+			//---- menuItem10 ----
+			menuItem10.setText("text");
+			popupMenu2.add(menuItem10);
+
+			//---- menuItem11 ----
+			menuItem11.setText("text");
+			popupMenu2.add(menuItem11);
+
+			//---- menuItem12 ----
+			menuItem12.setText("text");
+			popupMenu2.add(menuItem12);
+
+			//---- menuItem13 ----
+			menuItem13.setText("text");
+			popupMenu2.add(menuItem13);
+
+			//---- menuItem14 ----
+			menuItem14.setText("text");
+			popupMenu2.add(menuItem14);
+
+			//---- menuItem15 ----
+			menuItem15.setText("text");
+			popupMenu2.add(menuItem15);
+
+			//---- menuItem16 ----
+			menuItem16.setText("text");
+			popupMenu2.add(menuItem16);
+
+			//---- menuItem17 ----
+			menuItem17.setText("text");
+			popupMenu2.add(menuItem17);
+
+			//---- menuItem18 ----
+			menuItem18.setText("text");
+			popupMenu2.add(menuItem18);
+
+			//---- menuItem19 ----
+			menuItem19.setText("text");
+			popupMenu2.add(menuItem19);
+
+			//---- menuItem20 ----
+			menuItem20.setText("text");
+			popupMenu2.add(menuItem20);
+
+			//---- menuItem21 ----
+			menuItem21.setText("text");
+			popupMenu2.add(menuItem21);
+
+			//======== menu2 ========
+			{
+				menu2.setText("text");
+
+				//---- menuItem22 ----
+				menuItem22.setText("text");
+				menu2.add(menuItem22);
+
+				//---- menuItem23 ----
+				menuItem23.setText("text");
+				menu2.add(menuItem23);
+			}
+			popupMenu2.add(menu2);
+		}
+		// JFormDesigner - End of component initialization  //GEN-END:initComponents
+	}
+
+	// JFormDesigner - Variables declaration - DO NOT MODIFY  //GEN-BEGIN:variables
+	private JLabel label1;
+	private JLabel label2;
+	private JButton showPopupMenuButton;
+	private JButton showLargePopupMenuButton;
+	private JButton showPopupButton;
+	private JButton hidePopupButton;
+	private JButton movePopupDownButton;
+	private JButton movePopuprightButton;
+	private JLabel label4;
+	private JPopupMenu popupMenu1;
+	private JMenuItem menuItem1;
+	private JMenuItem menuItem2;
+	private JMenu menu1;
+	private JMenuItem menuItem3;
+	private JMenuItem menuItem4;
+	private JPanel popupPanel;
+	private JLabel label3;
+	private JPopupMenu popupMenu2;
+	private JMenuItem menuItem5;
+	private JMenuItem menuItem6;
+	private JMenuItem menuItem7;
+	private JMenuItem menuItem8;
+	private JMenuItem menuItem9;
+	private JMenuItem menuItem10;
+	private JMenuItem menuItem11;
+	private JMenuItem menuItem12;
+	private JMenuItem menuItem13;
+	private JMenuItem menuItem14;
+	private JMenuItem menuItem15;
+	private JMenuItem menuItem16;
+	private JMenuItem menuItem17;
+	private JMenuItem menuItem18;
+	private JMenuItem menuItem19;
+	private JMenuItem menuItem20;
+	private JMenuItem menuItem21;
+	private JMenu menu2;
+	private JMenuItem menuItem22;
+	private JMenuItem menuItem23;
+	// JFormDesigner - End of variables declaration  //GEN-END:variables
+}
diff --git a/flatlaf-testing/src/main/java/com/formdev/flatlaf/testing/FlatPopupTest.jfd b/flatlaf-testing/src/main/java/com/formdev/flatlaf/testing/FlatPopupTest.jfd
new file mode 100644
index 00000000..9b225101
--- /dev/null
+++ b/flatlaf-testing/src/main/java/com/formdev/flatlaf/testing/FlatPopupTest.jfd
@@ -0,0 +1,206 @@
+JFDML JFormDesigner: "7.0.4.0.360" Java: "16" encoding: "UTF-8"
+
+new FormModel {
+	contentType: "form/swing"
+	root: new FormRoot {
+		add( new FormContainer( "com.formdev.flatlaf.testing.FlatTestPanel", new FormLayoutManager( class net.miginfocom.swing.MigLayout ) {
+			"$layoutConstraints": "ltr,insets dialog,hidemode 3"
+			"$columnConstraints": "[fill][fill][fill][fill]"
+			"$rowConstraints": "[][][][][][]"
+		} ) {
+			name: "this"
+			add( new FormComponent( "javax.swing.JLabel" ) {
+				name: "label1"
+				"text": "Label with light-weight tooltip"
+				"toolTipText": "some tip"
+			}, new FormLayoutConstraints( class net.miginfocom.layout.CC ) {
+				"value": "cell 0 0"
+			} )
+			add( new FormComponent( "javax.swing.JLabel" ) {
+				name: "label2"
+				"text": "Label with heavy-weight tooltip"
+				"toolTipText": "some tip\n1\n2\n3\n4\n5\n6\n7\n8\n9\n10\n11\n12\n13\n14\n15\n16\n17\n18\n19\n20\n21\n22\n23\n24\n25"
+			}, new FormLayoutConstraints( class net.miginfocom.layout.CC ) {
+				"value": "cell 0 1"
+			} )
+			add( new FormComponent( "javax.swing.JButton" ) {
+				name: "showPopupMenuButton"
+				"text": "show light-weight JPopupMenu"
+				addEvent( new FormEvent( "java.awt.event.ActionListener", "actionPerformed", "showPopupMenu", false ) )
+			}, new FormLayoutConstraints( class net.miginfocom.layout.CC ) {
+				"value": "cell 0 2"
+			} )
+			add( new FormComponent( "javax.swing.JButton" ) {
+				name: "showLargePopupMenuButton"
+				"text": "show heavy-weight JPopupMenu"
+				addEvent( new FormEvent( "java.awt.event.ActionListener", "actionPerformed", "showLargePopupMenu", false ) )
+			}, new FormLayoutConstraints( class net.miginfocom.layout.CC ) {
+				"value": "cell 0 3"
+			} )
+			add( new FormComponent( "javax.swing.JButton" ) {
+				name: "showPopupButton"
+				"text": "show medium-weight popup"
+				addEvent( new FormEvent( "java.awt.event.ActionListener", "actionPerformed", "showPopup", false ) )
+			}, new FormLayoutConstraints( class net.miginfocom.layout.CC ) {
+				"value": "cell 0 4"
+			} )
+			add( new FormComponent( "javax.swing.JButton" ) {
+				name: "hidePopupButton"
+				"text": "hide"
+				addEvent( new FormEvent( "java.awt.event.ActionListener", "actionPerformed", "hidePopup", false ) )
+			}, new FormLayoutConstraints( class net.miginfocom.layout.CC ) {
+				"value": "cell 1 4"
+			} )
+			add( new FormComponent( "javax.swing.JButton" ) {
+				name: "movePopupDownButton"
+				"text": "move down"
+				addEvent( new FormEvent( "java.awt.event.ActionListener", "actionPerformed", "movePopupDown", false ) )
+			}, new FormLayoutConstraints( class net.miginfocom.layout.CC ) {
+				"value": "cell 2 4"
+			} )
+			add( new FormComponent( "javax.swing.JButton" ) {
+				name: "movePopuprightButton"
+				"text": "move right"
+				addEvent( new FormEvent( "java.awt.event.ActionListener", "actionPerformed", "movePopupRight", false ) )
+			}, new FormLayoutConstraints( class net.miginfocom.layout.CC ) {
+				"value": "cell 3 4"
+			} )
+			add( new FormComponent( "javax.swing.JLabel" ) {
+				name: "label4"
+				"text": "(switches to heavy-weight when moving outside of window)"
+			}, new FormLayoutConstraints( class net.miginfocom.layout.CC ) {
+				"value": "cell 0 5 4 1,alignx right,growx 0"
+			} )
+		}, new FormLayoutConstraints( null ) {
+			"location": new java.awt.Point( 0, 0 )
+			"size": new java.awt.Dimension( 490, 350 )
+		} )
+		add( new FormContainer( "javax.swing.JPopupMenu", new FormLayoutManager( class javax.swing.JPopupMenu ) ) {
+			name: "popupMenu1"
+			add( new FormComponent( "javax.swing.JMenuItem" ) {
+				name: "menuItem1"
+				"text": "text"
+			} )
+			add( new FormComponent( "javax.swing.JMenuItem" ) {
+				name: "menuItem2"
+				"text": "text"
+			} )
+			add( new FormContainer( "javax.swing.JMenu", new FormLayoutManager( class javax.swing.JMenu ) ) {
+				name: "menu1"
+				"text": "text"
+				add( new FormComponent( "javax.swing.JMenuItem" ) {
+					name: "menuItem3"
+					"text": "text"
+				} )
+				add( new FormComponent( "javax.swing.JMenuItem" ) {
+					name: "menuItem4"
+					"text": "text"
+				} )
+			} )
+		}, new FormLayoutConstraints( null ) {
+			"location": new java.awt.Point( 5, 395 )
+		} )
+		add( new FormContainer( "javax.swing.JPanel", new FormLayoutManager( class net.miginfocom.swing.MigLayout ) {
+			"$layoutConstraints": "hidemode 3"
+			"$columnConstraints": "[fill]"
+			"$rowConstraints": "[]"
+		} ) {
+			name: "popupPanel"
+			"background": new java.awt.Color( 153, 255, 153, 255 )
+			add( new FormComponent( "javax.swing.JLabel" ) {
+				name: "label3"
+				"text": "popup"
+			}, new FormLayoutConstraints( class net.miginfocom.layout.CC ) {
+				"value": "cell 0 0"
+			} )
+		}, new FormLayoutConstraints( null ) {
+			"location": new java.awt.Point( 225, 395 )
+			"size": new java.awt.Dimension( 200, 200 )
+		} )
+		add( new FormContainer( "javax.swing.JPopupMenu", new FormLayoutManager( class javax.swing.JPopupMenu ) ) {
+			name: "popupMenu2"
+			add( new FormComponent( "javax.swing.JMenuItem" ) {
+				name: "menuItem5"
+				"text": "text"
+			} )
+			add( new FormComponent( "javax.swing.JMenuItem" ) {
+				name: "menuItem6"
+				"text": "text"
+			} )
+			add( new FormComponent( "javax.swing.JMenuItem" ) {
+				name: "menuItem7"
+				"text": "text"
+			} )
+			add( new FormComponent( "javax.swing.JMenuItem" ) {
+				name: "menuItem8"
+				"text": "text"
+			} )
+			add( new FormComponent( "javax.swing.JMenuItem" ) {
+				name: "menuItem9"
+				"text": "text"
+			} )
+			add( new FormComponent( "javax.swing.JMenuItem" ) {
+				name: "menuItem10"
+				"text": "text"
+			} )
+			add( new FormComponent( "javax.swing.JMenuItem" ) {
+				name: "menuItem11"
+				"text": "text"
+			} )
+			add( new FormComponent( "javax.swing.JMenuItem" ) {
+				name: "menuItem12"
+				"text": "text"
+			} )
+			add( new FormComponent( "javax.swing.JMenuItem" ) {
+				name: "menuItem13"
+				"text": "text"
+			} )
+			add( new FormComponent( "javax.swing.JMenuItem" ) {
+				name: "menuItem14"
+				"text": "text"
+			} )
+			add( new FormComponent( "javax.swing.JMenuItem" ) {
+				name: "menuItem15"
+				"text": "text"
+			} )
+			add( new FormComponent( "javax.swing.JMenuItem" ) {
+				name: "menuItem16"
+				"text": "text"
+			} )
+			add( new FormComponent( "javax.swing.JMenuItem" ) {
+				name: "menuItem17"
+				"text": "text"
+			} )
+			add( new FormComponent( "javax.swing.JMenuItem" ) {
+				name: "menuItem18"
+				"text": "text"
+			} )
+			add( new FormComponent( "javax.swing.JMenuItem" ) {
+				name: "menuItem19"
+				"text": "text"
+			} )
+			add( new FormComponent( "javax.swing.JMenuItem" ) {
+				name: "menuItem20"
+				"text": "text"
+			} )
+			add( new FormComponent( "javax.swing.JMenuItem" ) {
+				name: "menuItem21"
+				"text": "text"
+			} )
+			add( new FormContainer( "javax.swing.JMenu", new FormLayoutManager( class javax.swing.JMenu ) ) {
+				name: "menu2"
+				"text": "text"
+				add( new FormComponent( "javax.swing.JMenuItem" ) {
+					name: "menuItem22"
+					"text": "text"
+				} )
+				add( new FormComponent( "javax.swing.JMenuItem" ) {
+					name: "menuItem23"
+					"text": "text"
+				} )
+			} )
+		}, new FormLayoutConstraints( null ) {
+			"location": new java.awt.Point( 5, 505 )
+		} )
+	}
+}