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

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