ADDITIONAL SYSTEM INFORMATION :
javafx-sdk-16
jdk 15.0.2
Fails: macOS 11.5.1
Succeeds: Windows 11

A DESCRIPTION OF THE PROBLEM :
- Consider a Stage with a Scene with a root Pane.
- The pane’s cursorProperty depends on whether the mouse button is down.
- The cursor in effect during a drag should stay the same when the user drags the cursor out of the window and then back in again.
- If the mouse button is released while outside the window, setting the cursor to the not-pressed state should succeed.

This works on Window 11 and fails on macOS.

STEPS TO FOLLOW TO REPRODUCE THE PROBLEM :
Run the source code below.

EXPECTED VERSUS ACTUAL BEHAVIOR :
EXPECTED -
Cursor stays the same as the cursor is dragged out of the window and back into the window.
If the mouse button is released while outside the window, setting the cursor to the not-pressed state succeeds.
ACTUAL -
Cursor changes to <–> as the cursor is dragged out of the window and stays as <–> as the cursor is dragged back into the window.

---------- BEGIN SOURCE ----------
package shop.examples;

import javafx.application.Application;
import javafx.beans.Observable;
import javafx.scene.Cursor;
import javafx.scene.Scene;
import javafx.scene.input.KeyEvent;
import javafx.scene.input.MouseEvent;
import javafx.scene.layout.Pane;
import javafx.stage.Stage;


public class ChangingCursor extends Application {

  Pane root;

  @Override
  public void start(Stage stage) {
    root = new Pane();
    root.setOnMousePressed (this::onMousePressed );
    root.setOnMouseReleased(this::onMouseReleased);
    root.setOnMouseEntered (this::onMouseEntered );
    root.setOnMouseExited (this::onMouseExited );
    root.cursorProperty().addListener(this::changedCursor);
    stage.setScene(new Scene(root, 300, 200));
    stage.show();
  }

  void onMousePressed (MouseEvent e) {
    System.out.println("pressed" ); root.setCursor(Cursor.CROSSHAIR);
  }
  void onMouseReleased(MouseEvent e) {
    System.out.println("released"); root.setCursor(Cursor.DEFAULT );
  }
  void onMouseEntered (MouseEvent e) {
    System.out.println("entered" ); root.setCursor(Cursor.HAND );
  }
  void onMouseExited (MouseEvent e) {
    System.out.println("exited" );
 // root.setCursor(Cursor.CLOSED_HAND); // has no effect
  }

  private void changedCursor(Observable ob, Cursor o, Cursor n) {
    System.out.println("changedCursor " + o + " " + n);
  }

  public static void main(String[] args) { launch(args); }
}
/*
  entered
  changedCursor null HAND
  exited
  // stays HAND
  entered
  // stays HAND
  pressed
  changedCursor HAND CROSSHAIR
  released
  changedCursor CROSSHAIR DEFAULT
  pressed
  changedCursor DEFAULT CROSSHAIR
  exited
  // cursor changed to <–>, with no change event
  released
  changedCursor CROSSHAIR DEFAULT <–– wrong; was <–> and stayed <–>
  entered
  changedCursor DEFAULT HAND <–– wrong; was <–>
  pressed
  changedCursor HAND CROSSHAIR
  exited
  // cursor changed to <–>, with no change event
  entered
  changedCursor CROSSHAIR HAND <–– wrong; was <–> and stayed <–>
  released
  changedCursor HAND DEFAULT <–– wrong; was <–> and stayed <–>
  // Here if you move the cursor,
  // it does change to DEFAULT, with no change event.
*/

---------- END SOURCE ----------

CUSTOMER SUBMITTED WORKAROUND :
Attempts to change the cursor from <–> to what it should be have no effect.

FREQUENCY : always