Where apps hide your files
Every photo ever sent to you in iMessage may be sitting on your disk. Finding them is the trick.
~/Library/Messages/Attachments/
Inside, a two-level hash structure (ab/cd/…) with each attachment in its own folder under a UUID. The chat database itself is ~/Library/Messages/chat.db.
Being inside ~/Library, none of it appears in Spotlight results.
du -sh ~/Library/Messages/Attachments
find ~/Library/Messages/Attachments -type f \( -iname "*.jpg" -o -iname "*.heic" -o -iname "*.mov" \) | wc -l
Years of conversations routinely hold tens of gigabytes here.
From Messages itself is cleanest: open the conversation → info button (ⓘ) → Photos / Documents tabs → right-click → Save. That copies it somewhere sensible without touching the store.
Directly from disk works too — the files are ordinary JPEG/HEIC/MOV — but treat the folder as read-only. Copy out; never reorganise in place.
Messages → Settings → General → Keep messages — switching from Forever to one year deletes older messages *and their attachments*, everywhere iCloud syncs. Understand that before flipping it.
More surgical: System Settings → General → Storage → Messages lists large attachments with delete buttons.
Attachments keep their original filenames (IMG_2041.HEIC, invoice.pdf), so a search tool that indexes ~/Library finds a document someone texted you the same as any other file — which is frequently where "I know I have it somewhere" files turn out to be.
~/Library/Messages/Attachments, in hashed subfolders. The conversation database is chat.db in the same Library folder.
Yes, and with Messages in iCloud the deletion syncs to your other devices.
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