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Was having the issue as well. I had AdGuard running, no VPN. What worked for me was deleting AdGuard. Not turning it off but completely deleting the app. Mail functions as expected now. I have "Protect Mail Activity" and "Hide IP" checked, as well as running the "Private Relay (Beta)" and the images load just fine after deleting AdGuard. Unfortunate as it was the only thing that blocked YouTube ads.
 
Was having the issue as well. I had AdGuard running, no VPN. What worked for me was deleting AdGuard. Not turning it off but completely deleting the app. Mail functions as expected now. I have "Protect Mail Activity" and "Hide IP" checked, as well as running the "Private Relay (Beta)" and the images load just fine after deleting AdGuard. Unfortunate as it was the only thing that blocked YouTube ads.
That bug is meant to be fixed in the latest Nightly build. If you don't want to install it there's another workaround, but it might occasionally hamper Safari.
 
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I had the same problem as everyone else. Read through the posts and saw that it might be an antivirus program causing the problem. Well, I installed Avast last night and the problem started up today when I checked my mail. I uninstalled Avast, checked the privacy boxes and shutdown Mail. Cranked back up and things were back to normal. Anyone suggest a "free" antivirus program....FYI I have tried Avira and liked it but after a few days it would just freeze and it would not update the latest virus definitions nor could you start a scan. So, check your antivirus as it might be the problem. Cheers
 
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I had the same problem as everyone else. Read through the posts and saw that it might be an antivirus program causing the problem. Well, I installed Avast last night and the problem started up today when I checked my mail. I uninstalled Avast, checked the privacy boxes and shutdown Mail. Cranked back up and things were back to normal. Anyone suggest a "free" antivirus program....FYI I have tried Avira and liked it but after a few days it would just freeze and it would not update the latest virus definitions nor could you start a scan. So, check your antivirus as it might be the problem. Cheers
“macOS includes built-in antivirus technology called XProtect for the signature-based detection of malware”

 
I've got "Protect Mail Activity" checked in Mail.app, but when I receive emails, images don't show and I get this banner at the top of the email: "Your network preferences prevent content from loading privately." along with a button I need to press called "Load Content Directly" which I need to press in order for email images to load.

I have a VPN, but it is never running. What other network preference could prevent the content from loading?
If you see 'Unable to load remote content privately' at the top of an email - Apple Support

View this at Apple Support for an explanation, https://support.apple.com/en-us/HT212797
 
I had the same problem as everyone else. Read through the posts and saw that it might be an antivirus program causing the problem. Well, I installed Avast last night and the problem started up today when I checked my mail. I uninstalled Avast, checked the privacy boxes and shutdown Mail. Cranked back up and things were back to normal. Anyone suggest a "free" antivirus program....FYI I have tried Avira and liked it but after a few days it would just freeze and it would not update the latest virus definitions nor could you start a scan. So, check your antivirus as it might be the problem. Cheers
I know others have responded, but I'll offer my two cents. Don't use anti-virus software on a Mac. It is not needed. Source: working for Apple for 5 years, using Macs for 15 years without anti-virus software, and spending more time than I can count fixing people's computers who installed anti-virus software. It often bogs things down and, worst case, installs garbage.
 
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I think I may have discovered the problem...

Does anyone use the Ghostery ad blocker for Safari from the Mac App Store? I was having other problems with their new app and I just completely uninstalled it and did a restart...and now Mail Privacy Protection works as intended. No more "your network preferences prevented..." error. No more needing to click any load remote content button.

After I uninstalled Ghostery, Mail Protection Privacy is working (Protect Mail Privacy and Hide IP address are both √ in Mail.app preferences) and all remote content loads in emails.

So Ghostery appears to have been the problem for me – not sure why as it's a Safari extension.

Can any one else try to delete Ghostery to see if they can confirm this fixes their issue?
 
I think I may have discovered the problem...

Does anyone use the Ghostery ad blocker for Safari from the Mac App Store? I was having other problems with their new app and I just completely uninstalled it and did a restart...and now Mail Privacy Protection works as intended. No more "your network preferences prevented..." error. No more needing to click any load remote content button.

After I uninstalled Ghostery, Mail Protection Privacy is working (Protect Mail Privacy and Hide IP address are both √ in Mail.app preferences) and all remote content loads in emails.

So Ghostery appears to have been the problem for me – not sure why as it's a Safari extension.

Can any one else try to delete Ghostery to see if they can confirm this fixes their issue?
Just now I've deleted it completely , restart and can confirm it is NOT the problem as far as I'm concerned .
 
Just now I've deleted it completely , restart and can confirm it is NOT the problem as far as I'm concerned .
How did you delete it? Just using the macOS method? I delete mine with CleanMyMac, which also deletes all its files it places all over your system.
 
I just updated to 12.1 and that issue in Mail appeared. I have no antivirus or any addons for safari or mail.

Only if I disable all the Privacy features it works as before. Is that the only way?
I see nothing in Network settings that enables me to use Mail as before.

EDIT: If I disable the feature in Network Settings "Limit IP adress tracking" it loads pictures. I don't feel this is the solution. Or is it supposed to work that way as some sort of protection? Does allowing to load for certain senders make pictures load in future or do we have to click on it every time we get an email from the same sender?
 
Hmm, so much for the claim from someone earlier in this thread that it was being fixed in 12.1.
 
I believe Mail uses the Safari web engine to load HTML. If you have an ad blocker installed on Safari, it will block Mail from loading certain images. The problem is that when I disabled my blocker, Mail must have dowloaded pictures in the background. Then turning the blocker back on doesn't do anything until new mail comes in. I've just whitelisted those two icloud sites mentioned earlier and I'll see if that helps.
 
I believe Mail uses the Safari web engine to load HTML. If you have an ad blocker installed on Safari, it will block Mail from loading certain images. The problem is that when I disabled my blocker, Mail must have dowloaded pictures in the background. Then turning the blocker back on doesn't do anything until new mail comes in. I've just whitelisted those two icloud sites mentioned earlier and I'll see if that helps.
I have no third party addons in safary or else.
 
I believe Mail uses the Safari web engine to load HTML. If you have an ad blocker installed on Safari, it will block Mail from loading certain images. The problem is that when I disabled my blocker, Mail must have dowloaded pictures in the background. Then turning the blocker back on doesn't do anything until new mail comes in. I've just whitelisted those two icloud sites mentioned earlier and I'll see if that helps.
Oh! I use 1Blocker. I'll disable it and see what happens in Mail.

Edit: Nope, no change.
 
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Oh! I use 1Blocker. I'll disable it and see what happens in Mail.

Edit: Nope, no change.
No anti-virus here and on Monterey 12.1 I have this issue! (I do not have this issue with my iOS devices!!)
 
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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 believe Mail uses the Safari web engine to load HTML. If you have an ad blocker installed on Safari, it will block Mail from loading certain images. The problem is that when I disabled my blocker, Mail must have dowloaded pictures in the background. Then turning the blocker back on doesn't do anything until new mail comes in. I've just whitelisted those two icloud sites mentioned earlier and I'll see if that helps.
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.
 
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I had "fixed" my problem by uninstalling Adblock in safari.

Today I enabled my VPN briefly. I got a message that my settings would not allow private relay. I subsequently disabled the VPN and although I've made no other changes the problem is back again.

No idea why this would be an issue, but something is definitely not right with this "feature" and now I'm back to clicking "load directly"in --every -.- single -.- message- - to see any pictures in all my email.
 
I had "fixed" my problem by uninstalling Adblock in safari.

Today I enabled my VPN briefly. I got a message that my settings would not allow private relay. I subsequently disabled the VPN and although I've made no other changes the problem is back again.

No idea why this would be an issue, but something is definitely not right with this "feature" and now I'm back to clicking "load directly"in --every -.- single -.- message- - to see any pictures in all my email.

I had an similar result. Even though I uninstalled the boot scripts, I'm still able to turn on the firewall manually and then turn it back off.

After booting without the scripts, all is good. I then turn on the firewall manually and it breaks. Then I turn off the firewall and it stays broken. I have to reboot to fix it again.

Basically, for me, if the packet firewall is ever turned on, the email privacy feature stops working until reboot. My VPN does insert rules in the packet filter firewall. Perhaps yours does too.
 
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