I'm probably missing something obvious, but I can get sendmail to give me AUTH PLAIN and LOGIN options. What I have is fairly standard configuration. The relevant part of sendmail.mc looks something like this: define(`confCACERT_PATH',`/etc/ssl/certs') define(`confCACERT',`/etc/ssl/ca-bundle.crt') define(`confSERVER_CERT',`/etc/ssl/smtp.crt') define(`confSERVER_KEY',`/etc/ssl/smtp.key') define(`confAUTH_OPTIONS', `A p') TRUST_AUTH_MECH(`EXTERNAL LOGIN PLAIN') define(`confAUTH_MECHANISMS', `EXTERNAL LOGIN PLAIN') DAEMON_OPTIONS(`Port=25, Name=MTA') DAEMON_OPTIONS(`Port=465, Name=TLSMTA, M=s') So basically, LOGIN and PLAIN should be offered when SSL/TLS is in use (but not for plaintext sessions). However, when connecting over TLS, sendmail doesn't advertise them: $ openssl s_client -connect localhost:465 [ SSL/TLS handshake output deleted, AES256 cipher was used ] 220 testbox.miliv.org ESMTP Unauthorized access prohibited EHLO localhost 250-testbox.miliv.org Hello localhost [127.0.0.1], pleased to meet you 250-ENHANCEDSTATUSCODES 250-PIPELINING 250-8BITMIME 250-SIZE 250-DELIVERBY 250 HELP Attempt to "brute-force" use them results in error (as expected): AUTH PLAIN 504 5.3.3 AUTH mechanism PLAIN not available I'm sure I'm missing something obvious here, probably a flag or two either in confAUTH_OPTIONS or in DAEMON_OPTIONS, but couldn't dig out which. Alraedy drank all coffe, and becoming desparate ;-) ---------------------------------------------------------------- This message was sent using IMP, the Internet Messaging Program.