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One of the greatest challenges in migrating my server from a managed FreeBSD server to the new OpenBSD server was learning how to implement support for SASL on SMTP connections. This seems like something so elementary in a mail server that it should be really simple. Unfortunately, simply installing the cyrus-sasl package doesn’t handle the integration with sendmail for you nor is there any really good documentation online. I was particularly disappointed that OpenBSD’s documentation was completely silent on how to do it.