I am looking for help figuring out a way to get all the photos and videos shared with me in a few conversations to appear in my Photos app on my Mac. I believe I have everything turned on to be automatically stored from my conversations, and I have an iCloud subscription with plenty of room. Yet, when I look at the iMessage conversation groups and the "Photos" section of those groups, it is only showing photos from the last few weeks.

It seems like I could download a lot of photos by going through the text of our messages and tapping on the download button next to photos, but it doesn't seem practical to do this for years of conversation with the few sets of conversations (mostly with my family) that I want to do this for.

What I've Tried:

  1. Enabling iCloud for Messages and Photos:
    • Verified that iCloud is enabled for both Messages and Photos on my iPhone and Mac.
  2. Using the "Shared with You" Feature in Photos:
    • Checked the "Shared with You" section in the Photos app, but it only shows recent media.
  3. Restarting Device and Toggling iMessage:
    • Restarted my devices and toggled iMessage settings, but the older media still doesn’t appear.
  4. Automator Application:
    • Created an Automator application to run a shell script that copies iMessage attachments to a folder on my Desktop.
    • Granted Full Disk Access to the Automator application.
  5. Python Script:
    • Wrote a Python script to query the chat.db SQLite database and extract attachments.
    • Faced authorization denied errors due to macOS privacy settings.
    • Granted Full Disk Access to Terminal and tried running the script, but the issue persisted.
  6. Terminal Commands:
    • Attempted to manually navigate to ~/Library/Messages/Attachments/ to copy files using Terminal.
    • Encountered permissions issues even after granting Full Disk Access to Terminal.

The Problem:

  • Undownloaded Media: Many of my iMessage conversations have numerous undownloaded media files (showing "Tap to Download").
  • Manual Downloading Not Feasible: Manually saving each item is not practical due to the sheer volume of media files.
  • Download Errors: Some older media files fail to download, displaying an "Unknown error".

What I Am Looking For:

  • Bulk Download Method: A way to bulk download all media files from Messages.
  • Automated Saving: A method to automatically save these downloaded items to the Photos app.
  • Cross-Conversation Solution: An approach that works across multiple conversations without manual intervention.

I am open to solutions using:

  • Built-in features
  • Automations (like Shortcuts)
  • Reputable third-party software
  • Terminal commands or scripts if using macOS

I have sufficient iCloud storage and understand the potential storage impact. Any effective solutions or even partial workarounds would be greatly appreciated.

Thank you in advance for your assistance!


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