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It is now nearly a day after I whitelisted the two Apple URLs used in Private Relay —
/mask.icloud.com/ and
/mask-h2.icloud.com/ —
and all new email in Apple Mail (Mac Monterrey) works well as intended.

I'm not certain why some folks have continued to have difficulty, but it is certainly not necessary to remove 1blocker if you whitelist the two URLs.

It's a pleasure having all pictures preloaded, too.
I am not using private relay (beta).
 
It is now nearly a day after I whitelisted the two Apple URLs used in Private Relay —
/mask.icloud.com/ and
/mask-h2.icloud.com/ —
and all new email in Apple Mail (Mac Monterrey) works well as intended.

I'm not certain why some folks have continued to have difficulty, but it is certainly not necessary to remove 1blocker if you whitelist the two URLs.

It's a pleasure having all pictures preloaded, too.
Where do I find the place to white list them ?
 
Where do I find the place to white list them ?
I mentioned in my original post I'm using 1Blocker ad blocker. They can be whitelisted by opening the 1Blocker app and entering the URLs in "Custom". Most other ad blockers have white listst, too. If you're not using an ad blocker and not using a VPN, I don't know why you might be getting the error message.
 
I mentioned in my original post I'm using 1Blocker ad blocker. They can be whitelisted by opening the 1Blocker app and entering the URLs in "Custom". Most other ad blockers have white listst, too. If you're not using an ad blocker and not using a VPN, I don't know why you might be getting the error message.
OK , thank you ! I didn't remember that.. senior moment I guess ;-)
 
I deinstalled Private Internet Access and rebooted. The problem persisted.

The only remaining thing I had was Murus firewall. This is just a front end used to configure the native packet filter firewall that comes with the OS. I used the program to disable the firewall. The problem persisted.

Then I used Murus to uninstall the boot scripts that configure the firewall. I then rebooted. The problem went away.

I might get in contact with Murus to see if there's something they can do to help. Even though I'm the one who tells Murus what firewall rules to apply, Murus has its own scripts that apply those rules. I would think that disabling the firewall should eliminate any restrictions I put into place, but maybe something else that Murus did was getting in the way.

It's really hard for me to blame any party having a hand in the problem in my situation - Apple, Murus, or me.

I have Murus and Vallum installed and I have the same issue.

Interested if you hear back from Murus. Definitely don’t want to remove Murus due to this issue.

Thanks for sharing.
 
I have Murus and Vallum installed and I have the same issue.

Interested if you hear back from Murus. Definitely don’t want to remove Murus due to this issue.

Thanks for sharing.

I did hear back from Murus today. Here's what they wrote...

macOS Private Relay is still a beta and it has several issues.
One of those issues is that it does not work when pf is enabled and the ruleset contains 'pass' or 'block' rules.
This happens with Murus, but it also happens with Apple's own Server.app.
We are all waiting for Apple to fix this.

Turning Murus off is not enough, to restore Private Relay you need to run this shell command from the Terminal:
sudo pfctl -f /etc/pf.conf

I had asked about the mail privacy as well as the private relay. The mail privacy is not in beta. I have a feeling the same technology underlies both features.

I tried the solution suggested and it didn't fix things. That is, if I enable the firewall just once, I am not able to get email privacy working again. I haven't tried enabling the firewall, but not using Murus to do it. Murus does a lot of default things in the scripts it runs when you use it to turn on the firewall.

It's going to take a bit of work to pin it down. Not that it's intellectually challenging, but every change that happens to break things requires a reboot to retest. Maybe the procedure I should follow is to try to enable the firewall with the default rules as specfied in pf.conf. Then, slowly add back in all the things that Murus does in its boot scripts, to find the thing that breaks it. If you've install the boot scripts, you can see that it all starts with /Library/Application Support/Murus/Scripts/pfstartup.sh. Perhaps their response applies to the mail privacy as well; as soon as I add a pass or block rule, I might see email stop working.

I'll probably get back in touch with Murus once I have a better sense. I don't want to waste their time if it's just a PF versus Apple problem.

I find the whole thing really puzzling. When would anyone configure a firewall and not use any pass or block rules? Did Apple think no one was using the packet filter? I need to study PF some more.

If I discover anything or get any more information from Murus, I'll absolutely post it here.
 
If I discover anything or get any more information from Murus, I'll absolutely post it here.

Only bad news to report from my experiments. It's trivial for me to break email/private relay and then fix it. No reboot is necessary. The Murus response seems entirely correct.

I configured my firewall manually (no Murus). I added nothing but a single block rule:

block in proto tcp from 123.123.0.1 to port 23123

That's a completely random IP address and port. (I tried a bunch of others.) Immediately after doing that, a popup appeared at the top right of my screen saying "Private Relay Unavailable - Your system settings are incompatible with Private Relay." Also, email started showing "Your network preferences prevent content from loading privately."

Then I deleted that block rule. Almost immediately a popup appeared at the top right saying "Private Relay is Active - Your IP address is hidden and your Safari browsing activity is protected." Also, email stopped showing that error message and images displayed in emails without any intervention by me.

I performed the exact same experiment with "block" replaced by "pass". I got the same results.

So, the private relay and email privacy seem to be stumbling over the same thing. If I choose to have this new Apple privacy stuff working, then I won't have any practical use for the PF firewall.
 
I experience the same issue. Here is my setup and the workaround that helps in my case:
  • macOS Monterey 12.1
  • Express VPN: Not connected all the time
  • Gmail, Hotmail and iCloud mail accounts configured in Mail
  • The macOS firewall is on under Security and privacy settings
  • I do not use iCloud private relay (beta) or any other security software (AV, special firewall rules, etc).
Mail works ok if I do not connect to the VPN. If I connect to the VPN while Mail is open I start to get this msg but the messages still load fine:
Screenshot 2021-12-31 at 06.48.05.png

When I close the VPN connection I start to get this message and the messages do not load correctly anymore, I then have to press the infamous Load content directly button:
Screenshot 2021-12-31 at 06.48.36.png

The only thing that fix the issue when it starts is a reboot.
The only way to avoid this happening in my case is to close Mail before I use my VPN. I can open Mail again once the VPN app is closed and it works fine.
Looks like something gets broken in my case when the VPN disconnects.
As reported by others everything works ok on the iPhone, the use of the VPN on iOS doesn't have any conflict with Mail.

Hope this can help some of you.

EDIT 2022-05-02: A pair of months ago this workaround stopped working. Now every single time I launch and close Express VPN Apple Mail shows the message, even if I use the VPN while Mail is closed. The only thing that gets rid of the message now is rebooting macOS. This is quite stupid. I have contacted Express VPN and they say that their app isn't doing anything wrong and as they have no control over Apple Mail there's nothing they can do.
 
Last edited:
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I did some experimentation and learned more about the problem with PF.

First off, I want to make sure everyone knows that there is a difference between the firewall that's visible in System Preferences and PF. The former is called the "application firewall" and the latter, the "packet firewall". The packet firewall is causing my issues.

PF is the firewall that is manipulated by the commercial Murus Firewall application. However, you don't need Murus at all to use and manipulate PF. PF is included with MacOS and has a command line interface.

I tried to manipulate PF (without using Murus) in the slightest possible way to cause the issue to arise. It turns out that just configuring the firewall, without following through and enabling that configuration, is enough to break email. Further, the simplest configuration that broke email for me is precisely the configuration that Private Internet Access establishes when I turn it on.

For those familiar with PF, to break email all you have to do is define an anchor in the main ruleset. You don't need to have anything else in the main ruleset. In addition, you don't need to load any rules into that anchor. And, as I already mentioned, you don't have to enable the firewall. Finally, when I turn on Private Internet Access, I see such anchors being defined.

The privacy features problem caused by PF can be fixed without rebooting. The simplest way I've found is to clear the main ruleset while the firewall is disabled and then enable the firewall. That immediately fixes the problem.

My conclusion is that the new privacy features are completely incompatible with any use of PF. And, some VPN's use PF in a way that would certainly trigger that incompatibility.
 
I did some experimentation and learned more about the problem with PF.

First off, I want to make sure everyone knows that there is a difference between the firewall that's visible in System Preferences and PF. The former is called the "application firewall" and the latter, the "packet firewall". The packet firewall is causing my issues.

PF is the firewall that is manipulated by the commercial Murus Firewall application. However, you don't need Murus at all to use and manipulate PF. PF is included with MacOS and has a command line interface.

I tried to manipulate PF (without using Murus) in the slightest possible way to cause the issue to arise. It turns out that just configuring the firewall, without following through and enabling that configuration, is enough to break email. Further, the simplest configuration that broke email for me is precisely the configuration that Private Internet Access establishes when I turn it on.

For those familiar with PF, to break email all you have to do is define an anchor in the main ruleset. You don't need to have anything else in the main ruleset. In addition, you don't need to load any rules into that anchor. And, as I already mentioned, you don't have to enable the firewall. Finally, when I turn on Private Internet Access, I see such anchors being defined.

The privacy features problem caused by PF can be fixed without rebooting. The simplest way I've found is to clear the main ruleset while the firewall is disabled and then enable the firewall. That immediately fixes the problem.

My conclusion is that the new privacy features are completely incompatible with any use of PF. And, some VPN's use PF in a way that would certainly trigger that incompatibility.
Good work!
 
Yes disabling all privacy settings for mail works. I'm happy with that.
I'm not.
Wiping the disk and reinstalling MacOS like it's any version of windows helped with the problem.
Seems like a new reality. Periodical system reinstallations for MacOS.
 
I'm having a mail issue where when I delete a message from my inbox it still shows in the inbox until I click on another folder. Then click back to my inbox and the message I had deleted has disappeared.
 
I've given up on Private Relay etc while in beta. It's got issues. I now use DNSCrypt on my Mac, a Quad9 config on my mobile devices, and installed MailTrackerBlocker on desktop while leaving Privacy Protection on, and Hide IP address > From Trackers on in Safari. It's a lot of stuff, but it works really well. If it comes out of beta I will try it again.
 
I'm not Aggedor, but thanks for the pointer! I discovered that pf was enabled on my Mac, and subsequently that macOS Server includes an adaptive firewall that uses it.

After I'd followed Apple's instructions for removing Server.app and rebooted the machine, the Mail app rediscovered how to download images.

Now I need to figure out how to disable Private Relay. I enabled it while I was trying to get the Mail app to download images, but now it re-enables itself every time I try to disable it. Oh well.

I didn't think about having installed the Server.app. I removed it, then CleanMyMac detected and removed everything else, rebooted and Mail is working as expected w/ the privacy settings. Thanks for mentioning this!!!
 
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I experience the same issue. Here is my setup and the workaround that helps in my case:
  • macOS Monterey 12.1
  • Express VPN: Not connected all the time
  • Gmail, Hotmail and iCloud mail accounts configured in Mail
  • The macOS firewall is on under Security and privacy settings
  • I do not use iCloud private relay (beta) or any other security software (AV, special firewall rules, etc).
Mail works ok if I do not connect to the VPN. If I connect to the VPN while Mail is open I start to get this msg but the messages still load fine:
View attachment 1936776
When I close the VPN connection I start to get this message and the messages do not load correctly anymore, I then have to press the infamous Load content directly button:
View attachment 1936779
The only thing that fix the issue when it starts is a reboot.
The only way to avoid this happening in my case is to close Mail before I use my VPN. I can open Mail again once the VPN app is closed and it works fine.
Looks like something gets broken in my case when the VPN disconnects.
As reported by others everything works ok on the iPhone, the use of the VPN on iOS doesn't have any conflict with Mail.

Hope this can help some of you.

EDIT 2022-05-02: A pair of months ago this workaround stopped working. Now every single time I launch and close Express VPN Apple Mail shows the message, even if I use the VPN while Mail is closed. The only thing that gets rid of the message now is rebooting macOS. This is quite stupid. I have contacted Express VPN and they say that their app isn't doing anything wrong and as they have no control over Apple Mail there's nothing they can do.
I just started having this issue after installing ExpressVPN. Even disabling ExpressVPN did not solve the issue. I finally fixed it by actually uninstalling ExpressVPN and then rebooting. I uninstalled by following this:

 
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