Normally, you can apply Transform > Auto to a batch of photos by syncing/copying with just the Upright Mode checked. The Auto transform settings will be recomputed for each target photo.
But if you accidentally sync/copy Auto mode to target photos with both Upright Mode and Upright Transforms checked, Auto won't be recomputed on the target photos, and they'll display the Update button in the Transform panel. This is as-designed.
If you try to correct the mistake by copying Auto mode again but with just Upright Mode selected, then Auto won't be recomputed on the target photos, and you'll have to click Update on them one by one. This is incorrect. The photos have become "poisoned", and no use of Sync, Auto Sync, or presets will compute Auto automatically on the entire batch -- you'll have to click Update on each photo individually. Too bad if there are hundreds of poisoned photos.
I've discovered just one way to clear the poisoned state other than clicking Update: Apply a preset that sets Upright Mode to Off, restart LR, and then apply a preset that sets Upright Mode to Auto. Unfortunately, this workaround only clears the poisoned state for the currently selected photo in Develop, not on an entire batch.
The preset behaves differently before the restart than after, conclusively demonstrating this is not "as-designed" behavior.
Steps to reproduce (also see the attached screen recording):
1. Create a new catalog. 2. Import two photos A and B. 3. Edit A. 4. Make a preset Upright Mode Off with just Upright Mode selected. 5. Click Transform > Auto. 6. Make a preset Upright Mode On with just Upright Mode selected. 7. Cmd-click B in the filmstrip, do Sync, with Upright Mode and Upright Transforms checked. 8. Select B, observe Update is displayed in the Transform panel. 9. In Transform, click Off, then Auto, and observe Update is displayed (wrong). 10. In the filmstrip, click A and cmd-click B. 11. Do Sync, with Upright Mode only checked. 12. Select B and observe Update displayed in the Transform panel (wrong). 13. Apply the Upright Mode Off preset. 14. Apply the Upright Mode On preset, observe Update (wrong). 15. Apply the Upright Mode Off preset. 16. Restart. 17. Apply the Upright Mode On Preset, observe no Update (correct).