Use VoiceOver cursor wrapping to navigate on Mac

When you use cursor wrapping, VoiceOver treats the items in a window or column as a continuous loop to make it easier to navigate.

Note: VO represents the VoiceOver modifier. See Use the VoiceOver modifier.

Open VoiceOver Utility (press VO-Fn-F8 when VoiceOver is on), click Navigation, then select Allow cursor wrapping.
Open VoiceOver Utility for me
To use wrapping, do any of the following:
- Wrap from the last item in a window to the top of the window: Press VO-Right Arrow.
- Wrap from the first item in a window to the bottom of the window: Press VO-Left Arrow.
- Wrap from an item at the bottom of a column (such as a list) to the first item in the next column: Press VO-Down Arrow.
- Wrap from an item at the top of a column (such as a list) to the last item in the previous column: Press VO-Up Arrow.

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VoiceOver User Guide