iMessage issue - images from old text conversations (when I had an Android) do not load

I moved from Android to iOS back in January. Ever since then, I have been unable to access images that I sent via text when I had my old phone. It appears as it does in the screenshot: a random filename, "JPEG Image · x KB". If I click on it, it "starts" to download but just says "Zero KB of x KB" and never loads any further. However, after I do that, a new prompt appears. If I look at the conversation info, right below "Delete and Block this Conversation", it says "1 image in iCloud - Download". But when I click on that, it says "Downloading" for a split second, and then it just loops back around to the first screenshot, as if I hadn't clicked on the image.


See these screenshots:





Things I have tried that didn't work:

  • Turning "Messages in iCloud" off and on multiple times
  • Turning iMessage off and on
  • Turning off everything under Siri & Search > Messages and turning it back on


This occurs on both my iPhone and my Mac, both of which have the latest updates installed (Sonoma 14.4.1 and iOS 17.4.1, respectively).

iPhone 15 Plus, iOS 17

Posted on Apr 20, 2024 1:24 PM

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iMessage issue - images from old text conversations (when I had an Android) do not load

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