Unable to load remote content privately

I’ve finally figured it out. Under System Preferences → Network → Ethernet/Wi-Fi → Advanced… → Proxies, I had Auto Proxy Discovery enabled.

I don’t use a proxy on my network, but I guess if you allow macOS to discover them automatically, Private Relay gets disabled “just in case” it finds one? Doesn’t make much sense to me 🧐

Either way, unchecking that option fixes the problem. Geolocation websites give me weird locations for my IP address, and Mail loads content privately.

There's a setting you need to turn off to resolve the issue. Go into Settings and then find the Mail App. Once there, scroll down to Privacy Protection. Turn off all of the toggles.

Disabling Adblock seems to be the only way I could get rid of "Unable to load remote content privately" (iOS/iPadOS 15.0 19A344).

Obviously not a preferred solution.

Apple has posted a support article, confirming that this feature does not work when using a VPN. However, what the article fails to mention is that you also cannot use an encrypted DNS .mobileconfig profile, which is what I was using (and which isn’t the same thing as a VPN).

So you pretty much have to disable all other privacy/security protections for your network in order to use this feature. Totally not worth it.

Private Relay and Mail Privacy Protection both work for me in iOS 15.1 and iPadOS 15.1 with AdGuard running, but I could never get it to work in Monterey.

When I first started troubleshooting, I discovered that I hadn't even enabled Private Relay (System Preferences -> Apple ID) on my Mac. Even after enabling it, I still received the "Unable to load remote content privately" message and had to manually press the button to view my emails.

I tried several things to no avail. I also tried troubleshooting it on both M1 (iMac and MacBook Pro) and Intel (iMac Pro) machines and had the same issue. Unfortunately, the only thing that worked for me was disabling AdGuard.

Turn battery power saving off

I was having this problem on my iPad Air 2, running iPadOS 15.0 (19A5307g).

I just upgraded to iPadOS 15.0 (19A5318f), and the problem has gone away.

This is not an “issue”, but intended behaviour to block the tracking of your actions when viewing emails by the sender or analytics services.

Of course, yes, if you don’t care about that, then you can disable the feature all together.

however, you should also notice at the top of each email there is a button to Load content if iOS was not able to do it privately for you but you want to be tracked and view the email.

If you’re on WiFi, go to Settings->WiFi tap the “i” to the right of the network you are connected to. Scroll down and turn on Private Relay. Force quit Mail and relaunch.

It has to do with the VPN toggle. If it’s switched on the content will say unable to load. But if you turn it off the email will load on its own.

You need to subscribe to iCloud+ (formerly iCloud Storage), then the option will appear under iCloud in Settings.

Private Address simply randomizes your device’s network identifier (MAC address) to make you harder to identify as you connect to various Wi-Fi networks. It is not related to Private Relay.

That makes sense. AdGuard Standalone functions like a VPN, which is incompatible with Private Relay and Mail Privacy Protection.

Now I really don’t understand why Safari tells me Private Relay is active when it’s clearly not.

I have no idea why this is recommended by Apple and upvoted as the solution. Disabling the feature entirely doesn’t solve the problem that the feature never worked, and continues not to work, in iOS 15 RC.

Mail Privacy Protection offers better privacy, in my opinion. A VPN will conceal your location, but Mail Privacy Protection will conceal when and how often you’ve opened an email. The best is to use Private Relay with Mail Privacy Protection, in which case you get both advantages.

However, Private Relay doesn’t filter all traffic on your device, whereas a VPN does.

Now that’s weird, because iCloud Private Relay and Mail Privacy Protection have never worked at all for me in macOS Monterey, including in 12.0.1 public release, which led me to believe it was just broken in macOS.

I’ve disabled my Encrypted DNS profile and AdGuard for Safari, and I don’t use a VPN. Safari’s Privacy Report states, “Your IP address is hidden from known trackers and websites you visit,” confirming that iCloud Private Relay is enabled.

Yet Mail is still unable to load remote content privately, and visiting whatismyip.com shows my public IP address from Frontier in a neighboring town, with no IPv6.

iOS 15 and iPadOS 15 work perfectly for both Private Relay and Mail Privacy Protection. Visiting whatismyip.com from either my iPhone or iPad lists an iCloud Private Relay/Cloudflare/Akamai IPv6 address connecting from a different state.