> On Jul 8, 2016, at 8:44 AM, Alastair Houghton <alast...@alastairs-place.net> 
> wrote:
> 
> It has a very high probability of being marked as spam, whatever headers you 
> use, because it’ll be delivered direct to the recipient’s mail server

Oh — I hadn’t thought of that. I sent my test email to myself, so of course it 
connected to my domain host’s SMTP. I just assumed that had come from my email 
settings.

Yeah, this is pretty unlikely to work these days, for the reasons Alastair 
gave. Any SMTP server but your own ISP’s / domain host’s is going to assume 
you’re a spam-bot.

The answer to “Why is it so hard to send email programmatically?” is basically 
“Because spammers.” (Also “because SMTP was designed in the 1970s/80s with no 
security considerations whatsoever, and we’ve never been able to graft proper 
useable security onto it, for reasons like backward compatibility and 
bike-shedding lack of consensus. Also, securing decentralized systems is hard.”)

—Jens
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