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Test environment
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Apple M1 Pro, macOS Ventura version 13.4

java version "20" 2023-03-21
Java(TM) SE Runtime Environment (build 20+36-2344)
Java HotSpot(TM) 64-Bit Server VM (build 20+36-2344, mixed mode, sharing)

openjdk version "21-ea" 2023-09-19
OpenJDK Runtime Environment (build 21-ea+23-1988)
OpenJDK 64-Bit Server VM (build 21-ea+23-1988, mixed mode, sharing)

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Test application
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SwingSet2.jar
SwingSet2 can be downloaded from:
https://docs.oracle.com/javase/tutorial/uiswing/lookandfeel/plaf.html#swingset2

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Test to reproduce bugs
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1. On macOS, start VoiceOver (for example with shortcut Option-Command-F5).

2. Start SwingSet2.jar with jdk-21 (or idk-20, which behaves the same).
-> SwingSet2 window is displayed. The Togglebutton “JInternalFrame demo” has the keyboard focus.

3. Press Right Arrow key once.
-> The ToggleButton “JButton JRadioButton JToggleButton JCheckbox demo” has the keyboard focus.

4. Press Space key.
-> The tab group “Button Demo” is shown.

5. Press Tab key three times.
-> The “One” button has the keyboard focus.
VoiceOver announces “Entering Buttons tab group. One, button. You are currently on a button. To click this button, press Control-Option-Space”.
Bug: VoiceOver does not announce the entering or the group with title "Text Buttons".
Expected announcement: "Entering Text Buttons group, One, button. ..."

6. Press Tab key 3 times.
-> The first image button has the keyboard focus.
VoiceOver announces “button. You are currently on a button. To click this button, press Control-Option-Space”.
Bug: VoiceOver does not announce the leaving of the group with title "Text Buttons" and the entering of the group with title "Image Buttons".
(Note: Apart from that, an accessible name is missing for the image button, for example a tooltip text.)
Expected announcement: "Leaving Text Buttons, Entering Image Buttons group, <accessible name>, button. ..."

Note 1: If you run this application on Windows OS together with the jaccessinspector.exe, you will notice that the panel title is transmitted as Parent name on Focus-gained-Event. (The jaccessinspector.exe is part of the openJDK and can be found in the /bin folder.)
Note 2: The mentioned bug does not occur with screen readers tested on Windows OS (tested with Jaws for Windows by Freedom Scientific, or NVDA by NVAccess).
Note 3: Mentioning a bug on VoiceOver announcement does not mean that the issue is on VoiceOver’s side, rather it is the result of the issue and the cause of the issue needs to be found.