[tombot]

I would have figured Apple proxied the preview to their own URL crawler which could automagically pluck the best preview image, similar to the magic that FB / Slack do when sharing a link. This would mask the IP / Geo and Apple could cache a preview image.

[pfg]

It would also expose any URL you send or receive via iMessage to Apple, whereas messages are otherwise end-to-end encrypted.

[tombot]

ah good point