> Jun 30 11:43:00 bottom sm-mta[18852]: AUTH: available mech=DIGEST-MD5 > CRAM-MD5 LOGIN PLAIN, allowed mech=EXTERNAL
Update here, it's not apparently an STARTTLS error, it's an AUTH error. Something in the update last night altered my list of available AUTH mechanisms. I manually updated sendmail.cf and updated this line: O AuthMechanisms=EXTERNAL DIGEST-MD5 CRAM-MD5 NTLM LOGIN PLAIN by adding "DIGEST-MD5 CRAM-MD5 NTLM LOGIN PLAIN" and now it accepts mail from my desktop. I don't see where this is configured. /etc/sasl2/Sendmail.conf which is a link to /etc/mail/sasl/Sendmail.conf.2, but this file looks good, I don't know where it's getting the AuthMechanisms from (yet).
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