Load remote images in iOS Mail

Recently I have been missing images and any linked images in my email in iOS. I did not change any settings or update recently. My email messages have a “load remote content” at the top of each email, which does load them. I have tried to look for the setting to change this, but it seems to be gone from the preferences, though if you search for Remote Images in Settings, it will show you the Mail preferences, but while in the actual preferences it does not seem to exist. (This is not just a TidBITS problem. It is all email.)

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Do you have Protect Mail Activity turned on (Settings > Mail > Privacy Protection)?

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I’m seeing the same issue in Mac Apple Mail for all my accounts. I was also not able to access a login page for my web hosting provider via Safari (geing rejected because I couldn’t pass their human vs. bot test). I was able to access the site via Firefox.

I think this may be related to the iCloud Private Relay issue. Note that the symptoms reposrted above are all with Private Relay turned off.

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Yes, but I have always had that on. Turning it off fixes the problem, but I would like to know why it changed. May be an Apple issue.

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Apple has recently had an outage with iCloud private relay that’s been messing things like that up.

As another data point. I have noticed that in some emails the images will display briefly then disappear. I assume this must be something at the Apple server not local.

I didn’t have the full Protect Mail Activity On, but I did have Hide IP Address turned on. Turning that off caused the mail issue to disappear. That setting probably uses the same channel as iCloud Private Relay.

I don’t think it’s related to the current Private Relay issue. I’ve been seeing this for months on my iPad, under both iPadOS 16 and 17. The only Mail privacy setting I had turned on was Hide IP Address, and emails with remote images always had a message saying something to the effect of “your settings prevent this content from loading” and the Load Remote Content button. Turning off Hide IP Address allowed images to load automatically.

My guess is that it’s actually a direct consequence of Hide IP Address. If the remote server holding the images can’t get your IP address, it doesn’t know where to send the images. Hide IP Address doesn’t work the same as Private Relay, which reroutes requests in such a way that the remote server still has a destination to send to, just not your IP address. Hide IP Address simply refuses to tell the remote servers where in netspace you are. So by withholding your IP address, you are de facto blocking automatic loading of remote images.