I understand how to do this I believe, which is to simply apply the Auto Transform to the first image, then select the rest of the interior images, then "Sync..." ->Transform -> Upright Mode.
1. Make sure that in the Synchronize Settings window, you've selected Upright Mode only:
When you select Upright Transforms or Transform Adjustments as well, LR will activate the Update button.
2. If 1 doesn't help, please report your exact version of LR (do Help > System Info).
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Thanks for the attempted assist John, but it turns out the current version of LR will not batch analyze Auto Transform as I was hoping it would. In fact this is why the "Update" button exists. It appears when Sync->Transform->Upright Mode only is checked, because LR will not analyze every image included in the sync. You must manually "Update" the Auto Transform for each image you have synchronized with the setting.
I spent a couple hours on the phone and in Remote Desktop sessions with Adobe techs this morning until finally a tier 3 tech came in to let us know that what I was attempting to do is not possible. This is a big disappointment and a huge PITA now that I have a couple thousand images in my workflow that I have to manually "auto" transform one at a time. I'm sure (praying) future versions of LR address this oversight.
Thanks again for trying to help,
Adobe support is mistaken (a not infrequent occurrence).
Here is a video showing LR CC 2015.7 properly syncing Upright Mode > Auto on 9 photos: https://dl.dropboxusercontent.com/u/21811200/sync-transform-auto.2016.11.10.mov.
I tried 100 photos and then 400 photos, in two different catalogs, a long-abused test catalog and a fresh catalog. I was able to reproduce your symptoms in the old test catalog -- I saw the Update button enabled on some of the photos after syncing. However, I then selected all the photos and did Library > Previews > Build Standard-Sized Previews. After the preview build completed, all of the thumbnails showed that Auto had been applied, and the Update button was no longer active. And after a couple iterations of this, the symptoms stopped occurring altogether.
I think this bug is a variant of a problem that LR has long had with large-scale batch operations. It tries to defer the recomputation of the thumbnails until they are actually visible in the Library grid, but sometimes it gets it wrong. For example, see this bug: Lightroom: Applying Auto Tone to a batch of photos loses subsequent develop settings | Photoshop Family Customer Communi… The workaround for that bug is the same -- invoke Build Standard-Sized Previews.
That's awesome man, I hope you're right. I have a couple thousand photos to test this out on tomorrow, will report back.