Apr 22 17:32:16 psf postfix/smtp: 2CDF8568E0: to=<email@example.com>, relay=mx4.hotmail.com[184.108.40.206]:25, delay=0.66, delays=0.02/0/0.48/0.16, dsn=5.0.0, status=bounced (host mx4.hotmail.com[220.127.116.11] said: 550 SC-001 (COL0-MC4-F23) Unfortunately, messages from 18.104.22.168 weren't sent. Please contact your Internet service provider since part of their network is on our block list. You can also refer your provider to http://mail.live.com/mail/troubleshooting.aspx#errors. (in reply to MAIL FROM command))
A theory about the fact that we are getting classified as a spammer: when an email is received from an unknown address, roundup send back a reply that you have to register to post. Since spammers use fake addresses, the victim of the spammer gets that message...and marks it as spam.
So we need to turn that off, and then figure out how to get off of hotmail's list (the URL included in the error is useless for that purpose).