Apple Mail "Load Content Directly" button vs. TidBITS email graphics

My TidBITS issue emails don’t show graphics embedded in articles. Instead, I have a blank box with a tiny white question mark against a blue background. Clicking this opens the graphic in Safari.

This started (I think) with the macOS Monterey 12.3.1 update. The TidBITS email has the banner at the top (which all my other emails that contain graphics do) that states “Your network preferences prevent content from loading privately.” However, unlike all my other graphic-containing emails, clicking the “Load Content Directly” button does not load the graphics in the TidBITS email.

My Mail > Privacy > Mail Privacy Protection > Protect Mail Activity option is selected, as well as the disabled “Hide IP Address” option. If I uncheck “Protect Mail Activity”, the problem goes away. So it appears there is something different about TidBITS emails compared to emails from all other sources (in my experience) that is preventing “Load Content Directly” from working.

Anyone else having the same experience?

P.S. Oddly enough, the one graphic that does show is the “This issue of TidBITS sponsored in part by” ad for textexpander.

Could be a difference between images that are sent as a part of the mail message (as an attachment) and “external” images, which are embedded links (and must pull the image from a web server in order to be displayed).

Privacy software will typically block external images, because the remote server can log who is trying to load them. They typically do not block attached images, since they can be displayed without sending any data to the Internet.

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I had exactly the same experience. I realize where they’re coming from and obviously it makes sense when dealing with potential spammers and bad actors, but to me it’s not acceptable to not get external images from trusted sources. I deactivated the feature first thing. I’ll reconsider once they add options for some granularity.

It sounds like there’s a bug here.

I don’t use Mail, but according to Apple support (Use Mail Privacy Protection on iPhone - Apple Support), the “Protect Mail Activity” isn’t supposed to block images.

It is supposed to do what the iOS equivalent feature does - by downloading images in a way that is supposed to make it hard for spammers to track the enclosing message.

The behavior you’re describing sounds more like the “Block All Remote Content” option.

FWIW, I use “Protect Mail Activity” on iOS. I’ve never seen a blocked image.

On my Mac, I generally use web mail services (Google, Yahoo and Mail.com), and occasionally use Mozilla Thunderbird. On all of these, I have them configured to not display external images. Each message is presented with a link/button I can click to load that message’s images. There’s also a link/button I can use to trust that sender with external images.

I think the button for trusting senders works by setting a property in that sender’s contact item (creating one if it doesn’t already exist).

Oh, absolutely. There was another discussion recently about the fact that the “Load Content Directly” button shouldn’t even be appearing at all. Turning on “Protect Mail Activity” should force images in emails to be loaded privately. Something seems to have recently broken that, and now the “Load Content Directly” button appears on every email that contains images. But the thing that makes this TidBITS-specific is that for me, clicking that button works for all other emails, but fails for TidBITS. I asked @ace privately if he had any idea what could be going on, but unfortunately not; hence this forum thread.

I have noticed that this also occurs when 1) Private Relay is not working (appears to happen very sporadically and briefly) or 2) when I am on a network that blocks private relay.

Those are good data points, Steven. In my case, System Preferences > Apple ID > Private Relay (Beta) is unchecked, so that does not seem to be a factor. And just to clarify, when you say you “noticed that this also occurs”, do you mean loading images in emails in general, or specifically the failure of the “Load Content Directly” button for TidBITS emails?

A bit of both. I usually only see the Load Contact Directly button when Private Relay is not functioning properly, and it is set to.

I have had it not work once or twice but not at all frequently

So another data point: In my original post, I mentioned that the one graphic that does load (and loads automatically) with “Protect Mail Activity” turned on is the one in the TextExpander ad. This image is sourced from here:

(https://textexpander.com/individual?utm_campaign=3D2021-q4-tidbits&utm_medium=3Ddisplay&utm_source=3Dtidbits&utm_content=3Dtidbits-v4)

All the other images (which do not load, even after pressing the “Load Content Directly” button) are sourced similar to this example:

(https://i0.wp.com/tidbits.com/wp/../uploads/2022/04/Q2-2022-category-pie-chart.png?ssl=3D1)

So it seems that there is some sort of conflict (at least in my case) between Mail and the “wp.com” site.

And to focus the thread to its intended scope (my bad), I will rename it from "Apple Mail ‘Protect Mail Activity’ vs. TidBITS emails.

wp.com is WordPress, since we’re using the Jetpack content delivery network for images.

Why that would be a problem, I can’t imagine.

We ran into a different problem with the Jetpack image CDN and disabled it at least temporarily, so, @fischej, if you want to test again without that on, perhaps it would shed some light on the situation.

Thanks, Adam. I pulled up the email for issue #1610, and all the images appeared automatically. I then turned “Protect Mail Activity” back on in Mail and re-opened that email. The images were still there. However, I’m not sure that was a good test. I think Mail caches the images locally, so I doubt it was trying to re-load them from the WP server. I’ll leave the “Protect…” option on in Mail, and test again when the next issue comes out on Monday (assuming you still have the Jetpack CDN disabled).

I’m seeing the same behavior as before with issue #1611. Protect Mail Activity selected, no images on first load, Load Content Directly button appears above the email, but when clicked nothing changes. Well, almost: Oddly, the one image that did load initially before (the ad for Textexpander) did not load initially this time, but–alone from all other images–did load when I clicked the Load Content Directly button.

At this point, if I’m the only one seeing this it’s hardly worth pursuing further. I guess we’ll just put it down to…gremlins? :slight_smile:

Sigh! Yeah, the Jetpack CDN is still off, so it’s more likely cosmic rays directed at your house. :-(

That’s why I’m so careful to always wear my tinfoil hat! :smiley: