Hi John,

OK, here's the whole thing again, with all 4 different cases built in.
Running it with no argument or 0 gives you my original code, 1 uses
Andrey's time-check, 2 uses the invokeLater() method to trigger the
button when the popup closes and 3 uses doClick().
My results are that it behaves the same for case 0 and 2 (broken) and
properly with the time check.
Although the doClick() option almost worked in the real code, in this
example it throws a null pointer exception - haven't been able to
figure out why yet :-( (btw. I get the exact same behaviour on OS-X and
RedHat linux)

Thanks again,

Steve
---- cut here ----
import java.awt.*;
import java.awt.event.*;
import javax.swing.*;
import javax.swing.event.*;

/*
* Standalone test of connecting a JToggleButton with a JPopupMenu.
* The goal is to have the toggle appear selected only while the popup
* is visible. When the popup is open, the user should be able to close
* the popup by:
*      1. clicking in the popup (a selection)
*      2. clicking anywhere outside the popup (cancel)
*      3. clicking on the toggle button again (raising the button and
*         canceling the popup)
* Everything works except the case 3.
* In this case the following happen:
*      Initial state: button is selected, popup is open
*      The user clicks the toggle button
*      The popup loses focus
*      The popup fires a cancel event
*      The popup fires an isClosing event
*      The popup becomes invisible
*      The button's action event is fired
*         => the button is not selected and the popup is closed
*      Problem: The action event NEVER sees the popup as being open or
*      the button as being selected
*
* Usage:
*    java PopupButton [0-3]
*
* Arguments:
*    0: display the original state - toggle button doesn't toggle
popup
*    1: use a delay to prevent triggering the toggle button twice
*       with one click
*    2: use invokeLater to delay triggering the toggle button
*    3: use doClick() to reset the button instead of setSelected()
*/
public class PopupButton
extends JFrame
implements ActionListener, PopupMenuListener {

   // start the test. Use any argument on the command line to use
   // invokeLater() to update the toggle button instead of directly
   // updating its status.
   public static void main( String[] args ) {
       int testNum = 0;
       if( args.length > 0 )
           {
           testNum = Integer.parseInt( args[0] );
           }
       final int testCase = testNum;
       javax.swing.SwingUtilities.invokeLater(
           new Runnable() {
               public void run() {
                   new PopupButton( testCase );
               }
           }
       );
   }

   public PopupButton( int testCase ) {
       this.testCase = testCase;

       setDefaultCloseOperation( EXIT_ON_CLOSE );
       getContentPane().setLayout( new FlowLayout() );

       button = new JToggleButton("click me");
       // events caught by actionPerformed() below
       button.addActionListener( this );

       popup = new JPopupMenu();
       // events caught by popupMenuWillBecomeInvisible() below
       popup.addPopupMenuListener( this );

       response = new JButton(
           new AbstractAction("thank you") {
               public void actionPerformed( ActionEvent e ) {
                   popup.setVisible( false );
               }
           }
       );

       String testCaseNames[] = {
           "broken triggers",
           "timed triggers",
           "triggering via invokeLater()",
           "triggering via doClick()" };
       getContentPane().add( new JLabel( "Testing " +
testCaseNames[testCase] ) );
       getContentPane().add( button );
       getContentPane().add( new JLabel(
                   "click here to close the popup " ) );
       popup.add( response );

       pack();
       setVisible( true );
   }

   // respond to the button's click actions by opening or closing the
   // popup
   public void actionPerformed( ActionEvent e ) {
       switch( testCase ) {
           case 1: // ensure a minimum delay before allowing another
event
               if ((System.currentTimeMillis() - lastEvent) < 250) {
                   // lastEvent = System.currentTimeMillis();
                   button.setSelected( false );
                   System.out.println( "button action: double-event,
deselecting button" );
                   return;
               } else {
                   System.out.println( "button action: double-event
time expired" );
                   lastEvent = System.currentTimeMillis();
               }
               break;
           default:
       }

       if( button.isSelected() ) {
           System.out.println( "button action: new popup" );
           Dimension d = button.getPreferredSize();
           popup.show( button, 0, d.height );
       } else {
           System.out.println( "button action: closing old popup" );
           popup.setVisible( false );
       }
   }

   // required by the PopupMenuListener interface
   // disable the toggle button when the popup closes
   public void popupMenuWillBecomeInvisible( PopupMenuEvent e ) {
       switch( testCase ) {
           case 1:
               System.out.println( "popup closing: deselecting button,
catching event time" );
               lastEvent = System.currentTimeMillis();
               button.setSelected( false );
               break;
           case 2: // use invokeLater()
               System.out.println( "popup closing: deselecting button
later" );
               javax.swing.SwingUtilities.invokeLater(
                   new Runnable() {
                       public void run() {
                           button.setSelected( false );
                       }
                   }
               );
               break;
           case 3: // use doClick()
               System.out.println( "popup closing: clicking button" );
               button.doClick();
               break;
           default: // broken
               System.out.println( "popup closing: deselecting button"
);
               button.setSelected( false );
               break;
       }
   }

   // required by the PopupMenuListener interface
   public void popupMenuCanceled( PopupMenuEvent e ) {}

   // required by the PopupMenuListener interface
   public void popupMenuWillBecomeVisible( PopupMenuEvent e ) {}

   //------------------------------------------------------------
   // ATTRIBUTES
   //------------------------------------------------------------
   private JToggleButton button;    // button to open popup
   private JPopupMenu    popup;     // popup panel
   private JButton       response;  // button in popup panel
   private int           testCase;  // which test case to run
   private long          lastEvent; // prevent the button being
pressed too quickly
}