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I use FastMail and love it, but I've noticed that if I use SMTP, it leaks my IP address in the email headers, whereas using the web client does not.

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That's how RFC2822 defines the email headers. That's not a leak, that's just how email works. When you send from the web app it uses that client as the originator.

This would be one of the cases the same text talks about "when users misunderstand the security characteristics". The journalist example can be used, but instead of checking an image sending a reply to the e-mail.

I'm unsure how many journalists know that their replies using an e-mail client will send their ip address, neither if they can understand why there is a difference between the mail client and their web interface.

I only know one organisation using fastmail services today, and I asked if they knew about this today, which of course they didn't. There surely are reasons to not break the RFC as gmail and others did, but the expectations from users need to be addressed somehow

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