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

Derek Clegg wrote:

In Mac OS Monterey, every email now shows "Your network preferences prevent content from loading privately." I have "Mail Privacy Protection: Protect Mail Activity" turned ON, and I want to keep it turned on. I do not have a VPN running. What can I do to fix this? I do not understand why this new feature fails so spectacularly right out of the box.

See if there is anything here:

If you see 'Unable to load remote content privately' at the top of an email - Apple Support

https://support.apple.com/en-us/HT212797

Apple-leaf wrote:

Open mail app select Mail > Preferences > Privacy ( last tab) and you will have to disable or untick - ' Protect Mail Activity ' , 'Hide IP address' & 'Block all remote content' , after this all the contents for the email will load automatically .

Hope solves the issue. :)

Note that while this will get rid of the message, it does so by turning off mail privacy protection.

Had same problem after updating to Monterey 12.2.1. At first I thought it was Avast and it may have been.

But there are a couple of fixes.

The first one is to go to System preferences > Network and uncheck "Limit IP Address Tracking." Interesting thing is that if you do that then the "Hide IP address from trackers" remain in place in both Safari and Mail apps. But I felt uncomfortable leaving any possible privacy helper turned off so I tried the second fix.

The second fix is one I found on an old MacOS comment site that I was very suspicious of. I don't know how or why it works but it does. I downloaded the app "Lulu" from "Objective-See" and set it up to run. You'll have to look at their website to check its specs. It monitors and controls outgoing network stuff? After you download it you have to open and turn it on. I did this on a laptop since I didn't trust it enough to run it on the iMac I use for business. I went back to System preferences and checked "Limit IP Address Tracking" back on. It worked. I'm not a computer geek or IT guy so I have no idea why it works. Maybe some of you gurus can figure out why.

It's only been a couple of days so I don't know if it's a permanent fix or not since I've found in the past that some OSX fixes

work today then not tomorrow ... HA! I'll update if mail goes back to its old shenanigans.

After trying everything suggested here without any luck I resorted to a clean install of macOS 12.0.1 Monterey and this worked. Protect Mail Activity now functions as expected.

Use of most proxy servers will interfere with the secure loading Mail tries to do.

Sys-Pref>network then on that screen on left side is WI-FI (mine is active)

when I click on WI-FI on left - it is to the right = limit ip address tracking checkbox

does that help?

Well, mine has spontaneously started working after upgrading to macOS 12.2. I didn't change any settings. Maybe it was the upgrade or just the reboot, but if you haven't updated yet, try that.

Make sure the 'Limit IP address Tracking' tick box in your network presences is not selected. This cleared it up for me.

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.

It’s the classic argument of security vs. convenience.

You got rid of the message telling you the content could not be loaded securely by… telling Mail not to download your content securely.

Now if it can’t be downloaded securely, it can either not present anything and leave you wondering why or not present it until you explicitly tell it to show it to you.

Now, why can’t it be loaded securely? That varies by network; in general Apple tries to load the content through a network of proxy servers, but there are various reasons why your device may not be able to.

One big reason right now is iCloud Private Relay, which has had slowdown issues over the past few weeks as you might expect when everyone is slamming those machines.

Another is if you are on a corporate network that does not allow access to those servers.

Finally some ISPs may also prevent access to those servers for a variety of reasons.

However, remember that even if you shut all the new security features off to avoid the message, you are being no more insecure than you were while running iOS 14.

About iCloud Private Relay - Apple Support

brigittefromwa wrote:

Whay would you send us to iPhone issues when we're talking about MacOS Monterey on our Mac's??

If every email  you see: "Your network preferences prevent content from loading privately.”

Open mail app select Mail>Preferences>Privacy  disable  “Protect Mail Activity” / “Hide IP address” / “Block all remote content” —content for the email will load automatically 

Use Mail Privacy Protection on Mac - Apple Support

Just another data point but in my particular situation, ENABLING my VPN (via Private Internet Access, not a corporate VPN) resolved those messages. With the VPN off, I see those messages on every email.

For reference, I switch between multiple Internet connections, each of which goes through a cell modem - one thru Verizon and one thru AT&T. Switching between connections didn't seem to make any difference.

The way to eliminate this is by going to: System Preferences➡️Network➡️ Uncheck limit ip address tracking

mikisdad wrote:

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

The problem is it can be one of several different settings, and it's hard to work out which one it might be in an automated way.

In fact, even if you know your way around it's hard to determine just what setting it's running afoul of.

It would be great if the message were made more specific, but such is the computing world of any flavor today:

Or you can go old school. 😁

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

Having a VPN enabled is the most common reason for issues with iCloud Private Relay, but is certainly not the only one.

he 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 ...

That's sadly true with any privacy mechanism as much of the Internet was designed to know as much about you as possible and use that knowledge accordingly.

For example, Warner Home Video had issues with iCloud Private Relay such that it used to send you to their Dutch website if you had it turned on because it couldn't detect where you were in the US.

Another example is the BBC won't allow you to play their videos if it can't detect you are in the UK.

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?

Because you can turn those options on if you are willing to live with the consequences.

It's kind of like installing a burglar alarm; it's a pain in the neck to use, or you can keep it turned off and you're no worse off than before you had the alarm installed.

Whether the hassles of turning the alarm on are worth it to you is a decision only you as the homeowner can make, but it's nice to have the choice.

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.