I don't think you can use gmail as a relay host unless Google is handling your domain's mail service (a GSuite account - not @gmail.com addresses). They have instructions for setting this up and the proper relay host once you've done the admin work is "relayhost = smtp-relay.gmail.com:587" (at least this works for me).
On Sat, Jun 22, 2019 at 9:58 PM Chris Pollock <cpoll...@embarqmail.com> wrote: > > On Sat, 2019-06-22 at 19:12 -0400, Wietse Venema wrote: > > Chris Pollock: > > > > Checking application/pgp-signature: FAILURE > > -- Start of PGP signed section. > > > In my previous post - "How to tell my ISP there's a problem" I > > > wasn't > > > able to figure out the problem and CenturyLink is no help so I > > > decided > > > to use my GMail account to send my messages from cron. However I've > > > run > > > into a problem that I keep getting the message that's in the > > > subject. > > > I've pasted the complete output of a test run below: > > > > > > https://pastebin.com/fLBqL1e0 > > > > Did you read the message? > > > > Jun 22 17:17:51 localhost postfix/smtp[11023]: C40181000BA2: > > to=<cpoll...@embarqmail.com>, > > relay=smtp.gmail.com[64.233.168.108]:587, delay=0.32, > > delays=0.05/0/0.24/0.03, dsn=5.5.1, status=bounced (host > > smtp.gmail.com[64.233.168.108] said: 530-5.5.1 Authentication > > Required. Learn more at 530 5.5.1 > > https://support.google.com/mail/?p=WantAuthError t30sm2748311otb.50 - > > gsmtp (in reply to MAIL FROM command)) > > > > And the web page in the link says: > > > > Outgoing Mail (SMTP) Server > > smtp.gmail.com <=== good. you use this. > > ...(requires SSL or TLS) <== good. you use this. > > Requires Authentication: Yes <== ERROR YOU ARE NOT DOING > > THIS. > > ... > > Port for TLS/STARTTLS: 587 <=== good. you use this. > > > > Account Name, User name, or Email address > > Your full email address > > > > Password > > Your Gmail password > > > > To configure SASL authentication, put your user name (Your full > > email address) and password (Your Gmail password) in smtp_sasl_passwd > > maps as described in http://www.postfix.org/SASL_README.html > > > > The text in /etc/postfix/sasl_passwd should look like: > > > > smtp.gmail.com Your-full-email-address:Your-Gmail-password > > > > and you should run "postmap hash:/etc/postfix/sasl_passwd" > > before using that file. > > > > Wietse > > I've spent 3hrs going over and over my settings and can't find where > I've got a problem. My /etc/postfix/sasl_passwd file contains: > > smtp.gmail.com:587 chris.pollock1...@gmail.com:********************* > > I've run postmap hash:/etc/postfix/sasl_passwd and still get the same > authentication error above and each time I run sudo postfix reload. I > know my password is correct because it's the same I use for fetchmail. > I even logged out and back in on my browser to be sure. > > -- > Chris > KeyID 0xE372A7DA98E6705C > 31.11972; -97.90167 (Elev. 1092 ft) > 20:40:08 up 2 days, 2:50, 1 user, load average: 1.69, 1.15, 1.07 > Description: Ubuntu 18.04.2 LTS, kernel 4.18.0-22-generic