iOS 18.1 Changed "Protect Mail Activity" Behavior

TidBITS Talk
1

Many or most of my emails in Mail on iPhone have been showing this lately:

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(with a tip of the hat to Doug for all the great TidBITS content).

Tapping “Load Content” always succeeds in loading the missing graphics, as expected. And clearly, this is an age-old technique for protecting my privacy by not indicating to spammers that I have opened their emails.

But why did it just start? And what are the “network settings” that are causing this?

Firstly, no, I’m not using a VPN. Apple Support got that wrong, too.

Then he suggested going under:

Settings > Mail > Privacy Protection

and turning off “Protect Mail Activity”, but that didn’t do it either. I had to also disable “Hide IP Address”, then quit and relaunch Mail, and then view the message again, before it would load the graphics automatically (ie, w/o me having to click “Load Content”).

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Okay, interesting.

But why and when did this change? Well, I’m running iOS 18.1, and this broke around when that was updated. So I went to my wife’s phone which is conveniently still running 18.0.1, and tested it on the same email message. Hers loads all the images fine, and she has Protect Mail Activity turned ON. (And mine was on, too, before all this went down).

So!

Unless I’m missing something, it seems that Apple has changed the behavior of Protect Mail Activity between 18.0.1 and 18.1. Or, introduced a bug. I thought I used to live in a very happy world where my images could load automatically, and still have all the privacy features Apple was offering. Now, it seems like Apple is saying “we are unable to hide your IP address if you download email images”. And the subtext is “we used to think we could, but we were wrong. In fact, all this time, we weren’t protecting you at all”. But that’s a bit speculative on my part. This could also just be a regression that will get fixed soon.

Anyone else notice this? Am I missing something?

2

If I recall correctly, “Protect Mail Activity” type settings (a feature offered by many email providers) download all graphics at the mail server level, regardless of whether an email is opened or not. This means a graphics-based tracker sees an IP address associated with your email provider without any differentiation of viewed and unviewed emails.

On the other hand, again if I recall correctly, “Hide IP Address” works by routing all data requests caused by viewing an email through proxy servers. This process will shield your device’s IP address but can indicate an email was viewed. In conjunction with data mining techniques, an email sender could be able to identify which emails were viewed, which were ignored, and, further, associate behaviors with a demographic profile.

So my guess is that the situation you’re experiencing is not the result of deceptive behavior by Apple but by either a bug or by the update causing some kind of network incompatibility in a buried or changed–don’t forget, Apple is notorious for undoing user configurations in updates–setting.

3

Well, using a VPN can definitely cause this so Apple Support wasn’t wrong to suggest that as a cause. What they might not have said though is that this message can also appear because of a problem on Apple’s relay servers.

1 Like
4

Yes. I had checked the web page for Apple services earlier in the week, and it said they were all up. That doesn’t mean something relevant but opaque to me isn’t down. But Apple Support made no apparent effort to look for anything like that.

5

I’m using 7.4.1 and no VPN and I’ve been getting this “feature” for a long time. I don’t remember when It started.

I’ve been waiting to upgrade to Sequoia as I’ve heard that many people are having mac mail issues. Does anyone know if those. issues have been solved?

6

Thanks for your reply!

Yes, Apple’s proxy servers (not your own mail server) will pull down the images. And by doing so from their own IP address, and on their own schedule, and regardless of whether you even open the email, the hide both your location and when you check your email, and whether you’ve forwarded it to someone else (since that other person would have fetched the same images from a different IP). What it won’t hide is that the message hit a legitimate mailbox, which can be useful information for dictionary spammers. But these are still useful features.

Yes. By hiding your IP, you hide your location, which also means they can’t tell if you forwarded it to someone far away. But I think in this mode, everything happens “on demand”, so the remote end knows when you check your email and how often, or perhaps that you never opened it.

To be clear, I never said it was deceptive. And per my comments above, I don’t think they or I changed any settings during an update. That’s why I compared the behavior on another phone still running 18.0.1, noting that it doesn’t present that “error” message, even when “Protect Mail Privacy” is enabled.

The more I read about how this works, the more this is feeling like a bug. The alternative explanation centers what they mean by “network settings”. Has the feature gotten smarter and now sees something about my network architecture that reveals information about me that undermines the effectiveness of this feature? And so whereas I had a false sense of security under 18.0.1, they’re now disabusing me of that illusion by telling me I may as well turn the whole thing off if I want to see the images?

7

When you say “this feature”, are you talking about the “Protect Mail Activity” feature, or the error message I showed at the top of each email containing graphic files?

8

Too me the “feature” is a bug. I’m referring to having to click on the “load content” line at the top instead of the content being in the body of the message.

1 Like
9

It would be a bug if it were not by design. Why would they give you a link to fix something that they didn’t expect to happen? It’s common in mail clients to give you control over whether images load. Outlook has had a feature like this for years, as well as control over whether you trust certain remote senders so you don’t have to do it each time, etc.

Anyway, I did a quick Google and found this, which appears to show older iOS how to Load Images in email:

​For the oldest iOS version (iOS 14 and earlier), please follow these steps:

  1. Select the My Settings icon.

  2. From the Settings menu on the left, select Mail > Contacts > Calendars.

  3. On the right, it will say Mail. Go to Load Remote Images and move the bar to the ON setting.