Gmail SMTP authentication and STARTTLS bug
Most SMTP servers don’t accept not encrypted connections, or require to secure such connection using explicit SSL.
Usually in such case LOGINDISABLED and STARTTLS are send in response to EHLO command. Some servers send STARTTLS and simply don’t send any AUTH responses.
Recently Gmail started to act differently (and incorrect):
S: 220 mx.google.com ESMTP hc4sm6305585wjc.9 - gsmtp
C: EHLO [192.168.0.11]
S: 250-mx.google.com at your service, [89.67.21.113]
S: 250-SIZE 35882577
S: 250-8BITMIME
S: 250-STARTTLS
S: 250-AUTH LOGIN PLAIN XOAUTH XOAUTH2 PLAIN-CLIENTTOKEN
S: 250-ENHANCEDSTATUSCODES
S: 250 CHUNKING
C: AUTH LOGIN
S: 530 5.7.0 Must issue a STARTTLS command first. hc4sm6305585wjc.9 - gsmtp
Server claims that it accepts LOGIN command:
S: 250-AUTH LOGIN
but when it is send, it claims that you must issue STARTTLS first:
S: 530 5.7.0 Must issue a STARTTLS command first. hc4sm6305585wjc.9 - gsmtp
This doesn’t make much sense and Gmail should not send “250-AUTH LOGIN PLAIN”.