Lightroom can't locate image in Apple Photos, "Masters" broken after Catalina upgrade.

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I recently upgraded to Catalina in Apple's OS. 

A bit of background on my workflow... I import all my photos into Apple Photos, then  edit photos in Lightroom by "Adding" them to Lightroom, but keeping the original file location in Apple Photos.

After the upgrade it looks like Apple has created a new "Masters" folder and moved all of my images to a "Masters.legacy" folder. Now all 30K of my photos are "missing" from Lightroom. I am unable to re-locate the original file because I can't get under the "Photos Library.photoslibrary" apple file through the file navigation in Lightroom.  Any ideas how I can re-link my files?
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Janelle Sheely

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Posted 9 months ago

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Just Shot Me

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First mistake Quote "I upgraded to Catalina".
Second mistake. Leaving all your images in the Masters folder and importing them into LR Classic without moving them out of that folder.

Look here to Reconnect them.

Find Missing Photos—how do I fix it? | The Lightroom Queen
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Carlos Cardona

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Read your 1st paragraph in horror! The worst approach to a workflow I can possibly imagine! In Photos you can choose “Add to Photos”, which ingests it into its inscrutable folder structure, and makes it REALLY DIFFICULT to extract. For years (before I used Lightroom) I turned off that setting to create a “reference library”, (the way Lightroom works), where you put the photos in one (or several) folders and THERE THEY STAY.

In Photos Right-click on any shot, say Show in Finder to open the folder it’s in. Once you know that location, go to LR and click on the “missing file” icon and say Find Photo. Navigate to your Photos folder you had found and find it there to relink it. Do it over and over.

It may find nearby folders, or you may decide to quit this process, put all the photos in one folder, and re-import them all. This may lose all your edits (I’m not sure of this)! Victoria? John?
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Carlos Cardona

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The link fromJust Shot Me gives valuable info about the relinking process!
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Victoria Bampton - Lightroom Queen, Champion

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> you may decide to quit this process, put all the photos in one folder, and re-import them all. This may lose all your edits 

Yes, bad idea, reimporting would lose all LR edits.
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Victoria Bampton - Lightroom Queen, Champion

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Hi Janelle

Hindsight is a wonderful thing, isn't it! As you've discovered, trying to use two different tools to manage the same set of photos is a problem.

Using Finder, you'll need to access the photos that are currently managed by Photos app and copy/move them to a normal folder structure. Once you've done that, then you'll be able to follow the instructions Just Shot Me posted, to reconnect Lightroom's records with the new location of the photos.

Once you've got that fixed, you might want to rethink your workflow to use either Photos or Lightroom. Trying to use both together is a bit of a recipe for disaster.
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Vickie Tuskan

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hi what do you mean a normal folder structure
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Carlos Cardona

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Photos are in folders, named by you the way you want to arrange them, and these all are in one main folder, which you could call “Lightroom Photos” or pretty much anything, but Lightroom Photos has a certain ring to it!
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Johan Elzenga, Champion

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Sounds like the photos are inside the Photos library file? That is a so-called ‘package’, a folder that looks like a file. Lightroom can’t look inside packages, so you need to open it manually and remove the ‘masters’ folder with the images and place it somewhere else. Right-click (or Ctrl-click) on the Photos Library package, and choose ‘Show package contents’.
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Janelle Sheely

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Thanks everyone. Yeah, hindsight is certainly 20/20. I've now learned the major flaw I had in not owning the organization of my file structure. I was hoping to get the best of both worlds with my weird workflow.

At least I have a backup of my system so I can get back to "normal" somewhat easily. I'll be moving my images out of Photos and controlling the file structure from now on.  Thanks again.