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Monterey Mail.app: "Your network preferences prevent content from loading privately."

GlenK said:
Think I stumbled on how to fix it. Go to Settings > WiFi > your WiFi network, tap on the i (info Button), then make sure iCloud Private Relay is turned on:

This corrected it for me and mail messages are loading properly now.
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Does this setting "use iCloud private relay" in your wifi settings turn on iCloud private relay for all of your internet traffic including web browsing in Chrome and non-Safari web browsers?
 
In my case it is happening when AdGuard protection is on. I haven't find a way to work with both adguard and mail protection enabled.
 
I'm using Private Internet Access as a VPN (but I usually have it turned off). After upgrading to Monterey, all I needed to do to resolve this problem was to launch the PIA app. It automatically added some new rules for WebKit apps to the exceptions, and after that I was good to go.
 
SW3029 said:
But when you then tick "Protect Mail Activity" the "Hide IP Address" just gets ticked again too.

The issue is we WANT "Protect Mail Activity" so we can privately load the images in an email.
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I agree in the long run I want the but in the short term this allows me to work.
 
SW3029 said:
What is Adgard? How do I disable it?
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Adguard is not part of MacOS. It’s a quite popular ad blocker and protection software, either as Safari extension or Mac computer wide app. And normally works well with the rest of MacOS functionality and ad removal.
 
dougmcarthur said:
I'm using Private Internet Access as a VPN (but I usually have it turned off). After upgrading to Monterey, all I needed to do to resolve this problem was to launch the PIA app. It automatically added some new rules for WebKit apps to the exceptions, and after that I was good to go.
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I use PIA here too, but this didn't make any difference for me.
 
Apple made the MacOS so "safe" it hardly work. I got email content to load automatically by un-selecting all the mail security features. In Mail Prefernces.
 
I have the issue as well.

I use Murus to configure the packet-level firewall. I also use Private Internet Access. I've disabled the firewall and updated PIA to the latest version, yet the issue persists.
 
I don't use any of these things, but the problem persists. I'm just going to have to turn the Mail privacy settings off until Apple fix it.
 
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Aggedor said:
Yeah, this is the exacct issue. We want these new mail privacy features that Monterey introduced. My wife's M1 MBA, also updated to Monterey, does not have this issue with Mail, and the settings are identical to my MBA.

So... it MUST be a bug.
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Says you. I'm pretty certain this is done on purpose.

Aggedor said:
I don't use any of these things, but the problem persists. I'm just going to have to turn the Mail privacy settings off until Apple fix it.
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Fix what?

If you click in More Info, you learn:

"Mail Privacy Protection

Emails that you receive may include hidden pixels that allow the email’s sender to learn information about you. As soon as you open an email, information about your Mail activity can be collected by the sender without transparency and an ability to control what information is shared. Email senders can learn when and how many times you opened their email, whether you forwarded the email, your Internet Protocol (IP) address, and other data that can be used to build a profile of your behavior and learn your location.

If you choose to turn it on, Mail Privacy Protection helps protect your privacy by preventing email senders, including Apple, from learning information about your Mail activity. When you receive an email in the Mail app, rather than downloading remote content when you open an email, Mail Privacy Protection downloads remote content in the background by default — regardless of how you do or don’t engage with the email. Apple does not learn any information about the content.

In addition, all remote content downloaded by Mail is routed through multiple proxy servers, preventing the sender from learning your IP address. Rather than share your IP address, which can allow the email sender to learn your location, Apple’s proxy network will randomly assign an IP address that corresponds only to the region your device is in. As a result, email senders will only receive generic information rather than information about your behavior. Apple does not access your IP address.

You can enable Mail Privacy Protection in Mail > Preferences > Privacy."

Having read this, I think we have two choices and one of them is to learn to live with it.
 
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mikehalloran said:
Having read this, I think we have two choices and one of them is to learn to live with it.
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I don't think it is working as intended. The error you get in an email is:

Your network preferences prevent content from loading privately (my emphasis).

From their description which you posted:

When you receive an email in the Mail app, rather than downloading remote content when you open an email, Mail Privacy Protection downloads remote content in the background by default — regardless of how you do or don’t engage with the email.

To me, this means that remote content in an email - images, etc - should be ready to view when you look at the email, as it has been downloaded in the background by default.

Therefore it should not require you to click a "load" button with a message saying that your network preferences are preventing private loading. There's either an incorrect setting, or a bug, that is (as the error message says) preventing remote content from being loaded privately - which is what the privacy setting is supposed to do, going by the exact wording of their description.
 
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Aggedor said:
I don't think it is working as intended. The error you get in an email is:

Your network preferences prevent content from loading privately (my emphasis).

From their description which you posted:

When you receive an email in the Mail app, rather than downloading remote content when you open an email, Mail Privacy Protection downloads remote content in the background by default — regardless of how you do or don’t engage with the email.

To me, this means that remote content in an email - images, etc - should be ready to view when you look at the email, as it has been downloaded in the background by default.

Therefore it should not require you to click a "load" button with a message saying that your network preferences are preventing private loading. There's either an incorrect setting, or a bug, that is (as the error message says) preventing remote content from being loaded privately - which is what the privacy setting is supposed to do, going by the exact wording of their description.
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Yes, this is correct. I have Private Relay and Protect Mail Activity enabled on my iPhone, iPad and M1 MBP and it all works as expected. Images load as soon as I select an email.
 
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mikehalloran said:
Says you. I'm pretty certain this is done on purpose.


Fix what?

If you click in More Info, you learn:

"Mail Privacy Protection

Emails that you receive may include hidden pixels that allow the email’s sender to learn information about you. As soon as you open an email, information about your Mail activity can be collected by the sender without transparency and an ability to control what information is shared. Email senders can learn when and how many times you opened their email, whether you forwarded the email, your Internet Protocol (IP) address, and other data that can be used to build a profile of your behavior and learn your location.

If you choose to turn it on, Mail Privacy Protection helps protect your privacy by preventing email senders, including Apple, from learning information about your Mail activity. When you receive an email in the Mail app, rather than downloading remote content when you open an email, Mail Privacy Protection downloads remote content in the background by default — regardless of how you do or don’t engage with the email. Apple does not learn any information about the content.

In addition, all remote content downloaded by Mail is routed through multiple proxy servers, preventing the sender from learning your IP address. Rather than share your IP address, which can allow the email sender to learn your location, Apple’s proxy network will randomly assign an IP address that corresponds only to the region your device is in. As a result, email senders will only receive generic information rather than information about your behavior. Apple does not access your IP address.

You can enable Mail Privacy Protection in Mail > Preferences > Privacy."

Having read this, I think we have two choices and one of them is to learn to live with it.
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Yeah, you have a misunderstanding of how this is supposed to work. You are SUPPOSED to be able to enable Mail Privacy Protection so the images in your emails will load remotely and privately yet you will still see them inline in the emails. That's the whole point of this feature: senders can't see when the images load (which is how they track you) but you can still see the images in their email.
 
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mzanker said:
Yes, this is correct. I have Private Relay and Protect Mail Activity enabled on my iPhone, iPad and M1 MBP and it all works as expected. Images load as soon as I select an email.
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Right! Which is not what happens on my MBA, despite all the settings being apparently correct, so it must be buggy. As lots of others in this thread are also experiencing.
 
I wonder, does anyone have this problem and have neither anti-virus nor VPN installed (or have the packet filter firewall turned on for some other reason)?

I have the packet filter firewall configured and enabled usually. I also notice that Private Internet Access installs rules into the filter. I'd imagine anti-virus might do the same, especially if it has a firewall component to it. I can also imagine other shenanigans that anti-virus programs might do (e.g. install certificates, modify routing tables).

EDIT

Just to be clear, the packet filter firewall is not the firewall configured in System Preferences.
 
svenmany said:
I wonder, does anyone have this problem and have neither anti-virus nor VPN installed (or have the packet filter firewall turned on for some other reason)?

I have the packet filter firewall configured and enabled usually. I also notice that Private Internet Access installs rules into the filter. I'd imagine anti-virus might do the same, especially if it has a firewall component to it. I can also imagine other shenanigans that anti-virus programs might do (e.g. install certificates, modify routing tables).

EDIT

Just to be clear, the packet filter firewall is not the firewall configured in System Preferences.
Click to expand...
You might be on to something. I have Private Internet Access on my MBA, and for work stuff I have FortiClient (not entirely sure how that works, as it doesn't seem to be a true VPN, it just allows me to access a work server remotely). I get the Mail issue.

My wife's absolutely identical MBA, also on Monterey, does NOT have the Mail issue. That machine has never had a VPN or anti-virus installed.

So the question is, how can I look at my packet filter firewall settings and compare it with my wife's MBA?

Edit: Actually, looking at your post above, it seems you've already tried this, and the problem persists?
 
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