Every email: "Your network preferences prevent content from loading privately". Why?

I encountered the same flaw, and eventually figured out that I could make Mail Privacy Protection work by disabling the Web filtering proxy Privoxy. I presume there's some Privoxy config tweak that will allow the two to coexist.

I'm sorry, I was referring to

I encountered the same flaw, and eventually figured out that I could make Mail Privacy Protection work by disabling the Web filtering proxy Privoxy. I presume there's some Privoxy config tweak that will allow the two to coexist.

wondered where/how this web filtering proxy was changed

I agree the whole thing isn't very clear. Why does the error send us to Network Preferences without clarity on what to do?

Protect Mail Activity now functions as expected

Update: the clean install enabled this to work for 2 days but has now reverted to always showing "Your network preferences prevent content from loading privately". Nothing in my setup has changed.

I first noticed this on my M1 MacBook Pro (Monterey) in the afternoon. Shortly thereafter The same problem occurred on my iPad Pro and then my iPhone 13 Pro. Oddly, my Apple Watch loads the content.

In the morning all was well in the world then but when I got home from getting my Moderna booster shot this problem began. Shall we start a conspiracy theory that anti-vaxxers are causing this? Just kidding, of course.

What is going on, people?

My wife's iPad Pro and iPhone 13 just started having this problem several hours after my problem started.

We don't use a VPN.

I reinstalled Monterey on my MacBook Pro - no change.

I guess we wait until Apple realizes they have a problem and then fixes it.

Clearly, you understand very much more about computing and networks than do I. However, one of the reasons I first became an Apple appreciator back in the days of the II+ and have continued to be so to the present day, is that Apple has continually provided not only high quality and aesthetically pleasing products but, more importantly for me, also made interfaces that work for - those who don't know ... - (Hypercard - the programming language for the rest of us) taught me much that helped me master relational databases some time later.)

So, for me, although your explanation makes perfect technical sense, it does not explain the lack of consideration for the user, particularly those who are not technically proficient. For instance:

The message doesn't indicate which 'network preference(s) is set inappropriately, let alone how to find and fix it.

The Apple Support explanation seems to indicate that it is purely a VPN issue when clearly it is not.

The inclusion of settings for protection "encourages" a user to take advantage of that protection yet Apple clearly know that in many cases this will cause the problem with content loading that it has ...

If, as you say, turning off all protection options will leave us no worse off than with the previous OS then what benefit does the change provide? - Why upgrade if one has to settle for how things were previously?

I sincerely hope that this does not come across as rude or abrasive. I don't mean it that way. I just feel a little disappointed that a company I have supported and held in high esteem for around 50 years, that began with a high priority on 'Human interface guidelines', seems to be less concerned with those in recent times.

However, I accept that despite my 50 years use of Apple computers, I know very little, so perhaps I am being unfair. I mean no offence.

I have to congratulate you on being the perfect apologist for Apple.

However, as I said: "So, for me, although your explanation makes perfect technical sense, it does not explain the lack of consideration for the user, particularly those who are not technically proficient. "

and as I also said:

I sincerely hope that this does not come across as rude or abrasive. I don't mean it that way. I just feel a little disappointed that a company I have supported and held in high esteem for around 50 years, that began with a high priority on 'Human interface guidelines', seems to be less concerned with those in recent times.

However, I accept that despite my 50 years use of Apple computers, I know very little, so perhaps I am being unfair. I mean no offence.

I guess then that I *am* being unfair in your estimation.

So be it. I stand suitably chastened.

I object to your classification of me as an Apple "apologist"; I gave a technical explanation of what goes on with network address obfuscation that has nothing to do with Apple and would have given the same explanation of the process were it Windows or UNIX/Linux.

Regardless, I do not feel you are being at all abrasive, I just wanted to give you a basic grounding in the factors involved.

Then I apologise for that, too. I'm sorry that I caused you offense.

I am an ignorant buffoon. I seem to manage to do this no matter how hard I try not to do it.

I stand even more suitably chastened.

Thanks. Yes, when I turned off the “Web Shield” in my AV (3rd party), it solved the problem of mail content not being automatically loaded without turning off “Protect Mail Activity”. Now I will check with the AV vendor to see what they say.

Just adding a "Me too", with no VPN and not network proxies.

And a nod to mikisdad, nice to see someone on here that's been here longer than me. II+! That beats my Macintosh Performa start by a few years. And I think I agree with all you are saying. :)

Rather than disabling Privoxy by unchecking "Web Proxy (HTTP)" and "Secure Web Proxy (HTTPS)" (via System Preferences->Network->Advanced->Proxies) , I tried bypassing the proxy settings for the *.icloud.com domains (which would include mask.icloud.com and mask-h2.icloud.com) and the *.apple-dns.net domains, but that did not work.

Could there be other domains that need bypassing to let Mail Privacy Protection work? Surely it's not simply because the protocols have been enabled that Mail Privacy Protection refuses to work?

I apologize, “limit ip address tracking” is found on the first screen after SysPref>network. Unchecking this option DID

WORK so images now load properly in Mail even with my AV fully enabled. Being a novice, does anyone know the

security ramifications of de-selecting “limit ip address tracking”?

Aw, dang. Wonder why it worked for me. There must be another setting as well. Perhaps the DNS servers you're using? Apple released a new OS version today for all devices - desktop & iOS. Are you up to date?

Then you will need to figure out what is different about your configuration that isn’t allowing this procedure to work.

Basically something isn’t allowing your device to load its content via Apple’s private servers.

If you aren’t using a VPN, then it’s usually a third party firewall or DNS redirector.