Apologies for resurrecting a somewhat old thread, but presumably the smtp_reply_filter fix won't work if smtp.gmail.com is now responding like:
$ telnet smtp.gmail.com 587 Trying 108.177.15.108... Connected to smtp.gmail.com. Escape character is '^]'. 220 smtp.gmail.com ESMTP b134sm26404242wmd.26 - gsmtp EHLO server.example.org 250-smtp.gmail.com at your service, [80.209.141.64] 250-SIZE 35882577 250-8BITMIME 250-STARTTLS 250-ENHANCEDSTATUSCODES 250-PIPELINING 250-CHUNKING 250 SMTPUTF8 ? Cheers, John -- Sent from: http://postfix.1071664.n5.nabble.com/Postfix-Users-f2.html