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I have been using Lightroom to mass develop my photos recently and all the tools work as expected when using automatic functions (e.g. auto WB, auto tone), that is setting an auto value will set it on all the selected photos and then determine the effect individually per photo.

E.g. Photo A is set to auto WB and has a different WB value compared to photo B which is also set to auto.

This however does not work for Transform, setting Transform to Auto will apply the exact same transformation on all photos, not determining the transformation individually but simply copying the value from the first selected photo on all photos.

I can always go in and click Auto in Transform on all photos manually but that's exactly what I don't want to do. How can I fix this?

I am using Lightroom Classic CC 7.5

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All transform corrections in post-production are going to be a compromise. They may distort the image in an undesirable way. Perhaps for this reason Adobe has not made the feature you request available inside Lightroom.

Upright can be copied (Copy Settings) or synchronized (Sync Settings), for use on one or more photographs. Two options have been provided in the Copy Settings and Synchronize Settings dialogs. The two options are:

Upright Mode

When you select Upright Mode, the mode that was selected is copied. However, the image that the settings were copied to, is corrected based on the content of the specific image.

Upright Transforms

Upright Transforms When you select Upright Transforms, the exact Upright transformation is copied/synced. Selecting the Upright Transform checkbox automatically will select the Upright Mode checkbox.

If you absolutely need an individual auto transform, you will need to use a third-party automation / macro tool.

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