After macOS Monterey 12.0.1 update my mail messages do not display any images

And the new name for "preferences" is "settings" ! So look for this in Mail - settings - privacy

P. Phillips wrote "... this feature was built into Monterey." This feature was said to have been built into Monterey. "This feature" was supposed to load content privately. But then it says the network preferences prevent the feature from working—without identifying the relevant network preferences. I want the feature.

It seems I would need to pay for iCloud+ in order for that feature to work. If you click on the question mark on the Privacy tab in Mail Preferences, and scroll down, you will find "Note: If you deselect the checkbox in Network preferences to use iCloud Private Relay (beta) for your Wi-Fi or Ethernet network, your IP address isn’t hidden from senders when using the network." But that checkbox isn't in Network preferences. It's in Apple ID preferences (in System Preferences).

OK, I subscribed to iCloud+, checked Private Relay (beta), verified that Protect Mail Activity was checked, and even restarted Monterey, and Mail is still telling me to Load Content Directly. I tried to cancel the iCloud+ upgrade but it's telling me I can't manage now. At any rate I've paid 99 cents and I'll have the upgraded iCloud+ for a month.

The feature does not exist.

To turn off the privacy functionality is not the point, the point is to be able to use the privacy feature as designed without this problem interfering with your emails.

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 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 message but the email messages still load fine:

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:

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.

Some others here have pointed out that not loading a tracking pixel protects you as far as your IP no. is concerned. That's true, HOWEVER, some trackers actually serialize the links to the tracking pixel. As a result, any access of a unique URL will indicate that you accessed your tracking pixel, and therefore, they know that the email they sent you was read, accessed, etc. At the very least, if you load the image they'll know that your email address is a good one.

To make this work better, Apple would need to create a cache of replicates for the emails to view and access. That would make the privacy feature work better, and more like what people expect and want.

Did you close mail and restart your machine ? And reopen Mail?

You do need the Hide IP box unchecked as well. Thank you for your help!

The Hide IP address box also needs to be unchecked (all three) to load images automatically.

I want to push the Load Content Directly button every time I want to see remote content. The Protect Mail Activity feature hides the IP address but also interferes with tracking pixels. Tracking pixels load when remote content is loaded. If I open an email message but don't load the remote content, tracking pixels aren't loaded.

Admittedly a working Protect Mail Activity would be better, as it would load remote content except for the tracking pixels. With the crippled Protect Mail Activity feature we have, we would get the same effect simply by checking both Hide IP Address and Block All Remote Content. But just checking Protect Mail Activity seems to be the better choice—in case Apple quietly fixes that feature.

I have Monterey on my iMac and MacBook, both with the exact same settings and the 'Protect Mail Activity' is checked on both. On the M1 MacBook mail is loading images but on the M1 iMac it is not?

When I uncheck it on the iMac it loads the images but check it again and the same problem happens.

That is an interesting explanation but it is still a terrible user experience. Basically anything other than a personal or work related email, includes images as core to the content. Having to click that button 30-40 times a day or more is obnoxious. I've shut it off, but this required unchecking all the privacy options available. So there is no way, apparently to have any sort of privacy protection without this rather annoying blocking of images. Seems wrong to me.

So I turned off both check boxes (which would actually be all 3 on the privacy screen) and now I have images!

Only having Hide IP address checked also prevents remote content/images displaying too.

This does work and is a helpful tip, however that makes the "Protect Mail Activity" feature in Apple Mail essentially useless since no one wants to push the "Load Content Directly" button every time they receive an email. This is a poor design and is not up to Apple's standards, in my humble opinion.

In Apples' efforts for Client Privacy, Protection and cutdown on Tracking - this feature was built into Monterey. That is not to say one Must use the feature if you do not what it. That option is still left to the User.

There is room for refinements and if there will be - may appear in future updates to Monterey.

All above is IMHO.

It seems to me that there is something wrong with the implementation of Mail Privacy in OS 12, as I have this feature switched on in iOS 15 on my iPad and the mail content still loads without my having to tap on it.