Gave up on my ISP, trying to get GMail to work but get - host smtp.gmail.com[64.233.168.108] said: 530-5.5.1 Authentication Required.

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Gave up on my ISP, trying to get GMail to work but get - host smtp.gmail.com[64.233.168.108] said: 530-5.5.1 Authentication Required.

Chris-3
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

Here is my main.cf

https://pastebin.com/1mmEP89b

I'm sure I have something just not right but I can't see what it is.

Thanks for any advise

Chris

--
Chris
KeyID 0xE372A7DA98E6705C
31.11972; -97.90167 (Elev. 1092 ft)
17:19:29 up 1 day, 23:29, 1 user, load average: 1.00, 1.00, 1.15
Description: Ubuntu 18.04.2 LTS, kernel 4.18.0-22-generic

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Re: Gave up on my ISP, trying to get GMail to work but get - host smtp.gmail.com[64.233.168.108] said: 530-5.5.1 Authentication Required.

Wietse Venema
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=<[hidden email]>, 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
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Re: Gave up on my ISP, trying to get GMail to work but get - host smtp.gmail.com[64.233.168.108] said: 530-5.5.1 Authentication Required.

Chris-3
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=<[hidden email]>,
> 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 [hidden email]:*********************

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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Re: Gave up on my ISP, trying to get GMail to work but get - host smtp.gmail.com[64.233.168.108] said: 530-5.5.1 Authentication Required.

Sonic
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 <[hidden email]> 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=<[hidden email]>,
> > 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 [hidden email]:*********************
>
> 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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Re: Gave up on my ISP, trying to get GMail to work but get - host smtp.gmail.com[64.233.168.108] said: 530-5.5.1 Authentication Required.

Viktor Dukhovni
In reply to this post by Chris-3
On Sat, Jun 22, 2019 at 08:56:35PM -0500, Chris Pollock wrote:

> 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 [hidden email]:*********************

Since your relayhost setting is:

  relayhost = [smtp.gmail.com]:587

Your SASL password should (IIRC) be either:

      [smtp.gmail.com]:587 [hidden email]:*********************

or

      smtp.gmail.com [hidden email]:*********************

the version without the [], but the port might not work, as it is
neither the full destination, nor the underlying host.

--
        Viktor.
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Re: Gave up on my ISP, trying to get GMail to work but get - host smtp.gmail.com[64.233.168.108] said: 530-5.5.1 Authentication Required.

Chris-3
On Sun, 2019-06-23 at 01:21 -0400, Viktor Dukhovni wrote:

> On Sat, Jun 22, 2019 at 08:56:35PM -0500, Chris Pollock wrote:
>
> > 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 [hidden email]:********************
> > *
>
> Since your relayhost setting is:
>
>   relayhost = [smtp.gmail.com]:587
>
> Your SASL password should (IIRC) be either:
>
>       [smtp.gmail.com]:587 [hidden email]:**************
> *******
>
> or
>
>       smtp.gmail.com [hidden email]:********************
> *
>
> the version without the [], but the port might not work, as it is
> neither the full destination, nor the underlying host.
Thank you for the reply Viktor. I've finally got it partially working
with my GMail account now and most of my cronjob messages are being
sent and returned to me as before. By adding the [ ] around the
smtp.gmail.com it started working.
I still have some that are going to /var/spool/mail/nobody however.
Headers below:

From [hidden email]  Sun Jun 23 09:01:26 2019
Return-Path: <[hidden email]>
X-Original-To: root
Delivered-To: [hidden email]
Received: by cpollock.localdomain (Postfix, from userid 0)
        id 3A4991000E12; Sun, 23 Jun 2019 09:01:25 -0500 (CDT)
From: [hidden email] (Cron Daemon)
To: [hidden email]

Though in my aliases file I have root set:

# Person who should get root's mail.  This alias
# must exist.
# CHANGE THIS LINE to an account of a HUMAN
root: [hidden email]

I'm sure it's something simple and I'll just have to read and reread
until I get it figured out. It was working well under my ISP until they
decided to start doing something to some of my outgoing cron messages
where they weren't being returned and some even marked as spam.

Chris

--
Chris
KeyID 0xE372A7DA98E6705C
31.11972; -97.90167 (Elev. 1092 ft)
09:08:27 up 2 days, 15:18, 1 user, load average: 0.67, 0.95, 0.95
Description: Ubuntu 18.04.2 LTS, kernel 4.18.0-22-generic

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Re: Gave up on my ISP, trying to get GMail to work but get - host smtp.gmail.com[64.233.168.108] said: 530-5.5.1 Authentication Required.

Wietse Venema
Chris Pollock:

> On Sun, 2019-06-23 at 01:21 -0400, Viktor Dukhovni wrote:
> > On Sat, Jun 22, 2019 at 08:56:35PM -0500, Chris Pollock wrote:
> >
> > > 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 [hidden email]:********************
> > > *
> >
> > Since your relayhost setting is:
> >
> >   relayhost = [smtp.gmail.com]:587
> >
> > Your SASL password should (IIRC) be either:
> >
> >       [smtp.gmail.com]:587 [hidden email]:**************
> > *******
> >
> > or
> >
> >       smtp.gmail.com [hidden email]:********************
> > *
> >
> > the version without the [], but the port might not work, as it is
> > neither the full destination, nor the underlying host.
>
> Thank you for the reply Viktor. I've finally got it partially working
> with my GMail account now and most of my cronjob messages are being
> sent and returned to me as before. By adding the [ ] around the
> smtp.gmail.com it started working.
> I still have some that are going to /var/spool/mail/nobody however.
> Headers below:
>
> From [hidden email]  Sun Jun 23 09:01:26 2019
> Return-Path: <[hidden email]>
> X-Original-To: root

All mail for root goes to nobody, if you're delivering mail with
procmail or the like.

Postfix expects that UNIX systems are used according this best practice:

- Log in as a real user, not as root.
- Use su (or sudo) for doing root stuff.
- Set up an alias root-> real user, and read mail as the real user.

        Wietse
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Re: Gave up on my ISP, trying to get GMail to work but get - host smtp.gmail.com[64.233.168.108] said: 530-5.5.1 Authentication Required.

Peter Ajamian
In reply to this post by Chris-3
On 24/06/19 3:38 AM, Chris Pollock wrote:
> I still have some that are going to /var/spool/mail/nobody however.
> Headers below:

And your logs show what exactly?


Peter
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Re: Gave up on my ISP, trying to get GMail to work but get - host smtp.gmail.com[64.233.168.108] said: 530-5.5.1 Authentication Required.

Chris-3
On Mon, 2019-06-24 at 08:00 +1200, Peter wrote:
> On 24/06/19 3:38 AM, Chris Pollock wrote:
> > I still have some that are going to /var/spool/mail/nobody however.
> > Headers below:
>
> And your logs show what exactly?
>
>
> Peter

The pastes are from my mail.log

https://pastebin.com/2kn42CRa

As I said earlier it all seems to be working correctly now.

--
Chris
KeyID 0xE372A7DA98E6705C
31.11972; -97.90167 (Elev. 1092 ft)
16:50:32 up 2 days, 23:00, 1 user, load average: 1.25, 1.20, 1.01
Description: Ubuntu 18.04.2 LTS, kernel 4.18.0-22-generic

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