This was my second hackernews submit [0]! So, not even https in 2014 :)

When I ran that server, outlook.com was also the only one that would blackhole my email for no known reason. Support was unhelpful and also could not point to any reason. I've since given up, but for a short time it was glorious, email to family would not leave the lan and we could send attachments of arbitrary size.

[0] https://news.ycombinator.com/item?id=7708882