Mail Privacy Protection: Every time I open an email with images I have to press "Load Content" manually. How can I fix it?

Question

Mail Privacy Protection: Every time I open an email with images I have to press "Load Content" manually. How can I fix it?

I am not using a VPN. I have tried disabling the Mail Privacy Protection feature and re-enabling it.

I experience the issue both when using my home wifi, work wifi, coffeeshop wifi, different countries, and mobile hotspot. So, while I wouldn't be surprised if my home wifi caused issues with it (my ISP puts a CGNAT in front of my home connection), it doesn't appear to be that either. Oh and I experienced the issue both on my previous MacBook Pro 13" M1 (late 2020), and on my current MacBook Pro M2 Pro (early 2023).

Any ideas?

MacBook Pro 14″

Posted on Aug 24, 2023 8:38 AM

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Answer 1

Top-ranking reply

largewoodenbadger Author

Level 1

8 points

Aug 24, 2023 9:19 AM in response to Barney-15E

That's probably true. My address is shared with ~50 other people who also use my ISP. So it's semi-anonymous.

I actually figured it the issue already: I had a VPN program installed (but not even open) and this was causing issues with iCloud Private Relay. I removed it and Private Relay started working immediately. This at least appears to have solved the issue with Mail as well.

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Answer 2

Barney-15E

Level 10

124,452 points

Aug 24, 2023 8:57 AM in response to largewoodenbadger

I don't know that anyone has figured out what "network settings" cause it to fail.

I seem to remember some people fixed it by reinstalling macOS.

I would imagine CGNAT could confuse it as your internet IP address is non-routable. It likely has no way to push the response from the anonymous relay back to your Mac.

The CGNAT seems like it pretty much anonymizes your public address anyway.

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Answer 3

Barney-15E

Level 10

124,452 points

Aug 24, 2023 8:40 AM in response to largewoodenbadger

Since it cannot load through the double relays, you have to disable all of the items in Mail Privacy.

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Answer 4

Aug 24, 2023 8:42 AM in response to Barney-15E

That's an obvious workaround, but I'd rather make it work if possible? The feature has been around for over two years and it has never worked for me, that seems very surprising and disappointing to me.

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Mail Privacy Protection: Every time I open an email with images I have to press "Load Content" manually. How can I fix it?

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