This is my problem-Sent this to Apple :
I am reporting a persistent iCloud Messages issue that appears to be an attachment-indexing defect. Below is a concise summary of the problem, troubleshooting to date, and reproducible steps.
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Issue Summary
• What happens:
• When I send a camera-roll photo (with or without text), the image appears in the conversation on all devices but does not appear in the Info → Photos gallery on my iPhone or Mac.
• Screenshots I send index correctly on all devices.
• Photos I receive index correctly on all devices.
• Affected devices: iPhone [model] on iOS 26.x and Mac [model/macOS version].
• Not affected: iPad [model/iPadOS version], which indexes both camera-roll photos and screenshots properly.
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Troubleshooting Performed
• Toggled Messages in iCloud off and on with “Disable & Download Messages” multiple times.
• Signed out and back in to iMessage on all devices.
• Erased and Set Up as New iPhone (no restore from backup).
• Clean, brand-new iPhone running iOS 26 showed the same behavior as my previous phone.
• Maintained ideal conditions (ample free storage, strong Wi-Fi, plugged in and unlocked for extended periods).
Despite these steps, the issue persists.
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Reproduction Steps
1. From my iPhone, send:
• A camera-roll photo (with or without text).
• A screenshot.
2. Observe on iPhone and Mac:
• Both images appear in the chat thread.
• Only the screenshot appears in Info → Photos.
3. Observe on iPad:
• Both the camera-roll photo and the screenshot appear in Info → Photos.
I have attached screenshots and timestamps documenting these tests.
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Why This Is a Bug
• The fact that the iPad indexes all images correctly proves that iCloud is storing and categorizing the attachments properly.
• Two different iPhones (including a brand-new iOS 26 device) and a Mac consistently fail to index outgoing camera-roll photos, which points to an iOS/iCloud indexing defect specific to my Apple ID.
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Requested Action
Please escalate this case to iCloud / Messages engineering for analysis and resolution.
I would appreciate confirmation that this is filed as an engineering issue and notice when a fix is planned for an upcoming iOS 26.x release.
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Thank you for your time and for reviewing the attached evidence.
I am happy to provide diagnostic logs or conduct additional tests if needed.