Mail "Load content directly" doesn't work on Mac - why?

Living Fossil wrote:

On my MacBook Pro, running Sonoma 14.3.1, I get some emails from non-spam sources (for example, my home insurance company, with proper identifying details), where some non-loaded content is represented by a little square with a question mark in it. Mail says it can't download the content directly: there's a button "Load Content Directly" but it doesn't do anything. Clicking or right-clicking on the little square doesn't do anything either. If I look at these mails on my iPhone, I can see the same mail without problems, but there doesn't seem to be additional content corresponding to the square seen on the Mac. This didn't used to happen - what's going on and how can I get the system to work properly?

Open Mail.app select Mail>Settings>Privacy disable:

Protect Mail Activity

Hide IP address

Block all remote content

compare your results,

If no resolve see:

—if you are using Hide My email—try disabling this feature and compare your results...

Set up and use Hide My Email in iCloud+ on all your devices - Apple Support

—if you are using iCloud Private Relay on Mac - Apple Support try disabling this feature and compare your results...

Use iCloud Private Relay on Mac - Apple Support

Living Fossil wrote:

Do you think it's worth asking Apple Support about it?

Thanks again for your suggestions.

Apple Support gets paid to drill down on issues and or escalate up the chain of command if no insight

Call Customer Support  (800) MY–APPLE (800–692–7753)

or on line  https://getsupport.apple.com/

Outside the USA—Contact Apple for support and service by phone

See a list of Apple phone numbers around the world.

Contact Apple for support and service - Apple Support 

If you’ve turned off all of the mail, privacy options, and the load content button directly doesn’t work either, I would say there is something in your network settings that is blocking access to the server that hosts those files. The only two things I can think of are a firewall or some sort of Internet security.

Remote content is almost always insignificant. I can’t think of a time when I’ve ever had remote content that provided any benefit to me. It is normally just spam.