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This appears to have nothing to do with greylisting and is because of a 550 code by mimecast. Nov 16 15:56:01 mail2 postfix/smtp[24776]: 404853F264: to=<USER@RECIPIENT.COM>, relay=je-smtp-inbound-1.mimecast-offshore.com[213.167.81.36]:25, delay=0.63, delays=0.08/0/0.45/0.1, dsn=5.0.0, status=bounced (host je-smtp-inbound-1.mimecast-offshore.com[213.167....


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This answer is heavily inspired by @RedScourge's original answer, but disables LookupIP via config and makes minimally invasive changes to the sshd script only if necessary. I experienced Google blocking logwatch emails as well. They never made it to the recipient's spam folder; Google blocked the email on the way out. @RedScourge's analysis that this is due ...


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