[gentoo-user] Re: Computer system email no not working since gmail change.

[Grant Edwards <grant.b.edwards@gmail.com>]

On 2024-09-27, Dale <rdalek1967@gmail.com> wrote:

>>> Sep 26 19:04:26 Gentoo-1 smartd[18737]: Executing test of <mail> to root ...
>>> Sep 26 19:04:36 Gentoo-1 msmtp[18815]: host=smtp.gmail.com tls=on
>>> auth=off from=rdalek1967<at>gmail.com recipients=root errormsg='the
>>> server sent an empty reply' exitcode=EX_PROTOCOL
>> According to that message, the msmtp auth option is off.  It needs to
>> be on.

> This is what I copied from yours, with obvious bits changed.  I'll put
> "noneya" in those, so you know that isn't the real info. 
>
> syslog LOG_MAIL
>
> account    default
> maildomain gmail.org
> syslog on
> from rdalek1967<noneya>gmail.com
> host smtp.gmail.com
> port 465
> tls on
> tls_certcheck off
> tls_starttls off
> auth on
> user rdalek1967@gmail.com
> password "noneya"  # That is the 16 character thing with spaces in it. 

That's not the config that msmtp is using.  See in the log where it
says "auth=off"?  It should say "auth=on".  And I think it's also
using the wrong port number (or you should turn tls_startls off).

Here's what my log looks like:

    Sep 26 15:57:47 aleph msmtp[21363]: host=smtp.gmail.com tls=on auth=on user=grant.b.edwards@gmail.com from=grant.b.edwards@gmail.com recipients=<deleted>@<deleted>.com mailsize=317 smtpstatus=250 smtpmsg='250 2.0.0 OK  1727384267 e9e14a558f8ab-3a344d605d5sm1326875ab.7 - gsmtp' exitcode=EX_OK

> I'm by no means a expert on this but I see 'auth on' in there.  I see
> what you talking about in the error to tho.  As I mentioned in other
> reply, I think something else is amiss somewhere.  If that config works
> with gmail for you, it should work here. 

msmtp is not using the configuration you showed above.

> On the root thing, I have a alias set up in some file that tells it that
> root is my gmail address.  It worked before but maybe not now.  File is
> here:  /etc/mail/aliases  It has this info about root being my gmail
> address. 

Msmtp doesn't read an alias file by default. You need to add an alias
command to the msmtp config:

    alias /etc/mail/aliases

Then run msmtp from the command line like this so you can see all the
settings and the messages exchanged.  Pay particular attention to
where it's reading the configuration from, port number, and
tls_starttls.  Also look to see where it's reading aliases from.

    $ echo foo | msmtp -v bogus
    
    msmtp: recipient address bogus not accepted by the server
    msmtp: server message: 553-5.1.3 The recipient address <bogus> is not a valid RFC 5321 address. For
    msmtp: server message: 553-5.1.3 more information, go to
    msmtp: server message: 553-5.1.3  https://support.google.com/a/answer/3221692 and review RFC 5321
    msmtp: server message: 553 5.1.3 specifications. 8926c6da1cb9f-4d8888f9f55sm483180173.166 - gsmtp
    msmtp: could not send mail (account default from /etc/msmtprc)
    loaded system configuration file /etc/msmtprc
    ignoring user configuration file /home/grante/.msmtprc: No such file or directory
    falling back to default account
*** using account default from /etc/msmtprc
    host = smtp.gmail.com
*** port = 465
    source ip = (not set)
    proxy host = (not set)
    proxy port = 0
    socket = (not set)
    timeout = off
    protocol = smtp
    domain = localhost
*** auth = choose
    user = grant.b.edwards@gmail.com
    password = *
    passwordeval = (not set)
    ntlmdomain = (not set)
*** tls = on
*** tls_starttls = off
    tls_trust_file = system
    tls_crl_file = (not set)
    tls_fingerprint = (not set)
    tls_key_file = (not set)
    tls_cert_file = (not set)
    tls_certcheck = off
    tls_min_dh_prime_bits = (not set)
    tls_priorities = (not set)
    tls_host_override = (not set)
    auto_from = off
    maildomain = gmail.org
    from = grant.b.edwards@gmail.com
    from_full_name = (not set)
    allow_from_override = on
    set_from_header = auto
    set_date_header = auto
    remove_bcc_headers = on
    undisclosed_recipients = off
    dsn_notify = (not set)
    dsn_return = (not set)
    logfile = (not set)
    logfile_time_format = (not set)
    syslog = LOG_MAIL
*** aliases = (not set)
    reading recipients from the command line
    TLS session parameters:
        (TLS1.3)-(ECDHE-X25519)-(ECDSA-SECP256R1-SHA256)-(AES-256-GCM)
    TLS certificate information:
        Subject:
            CN=smtp.gmail.com
        Issuer:
            C=US,O=Google Trust Services,CN=WR2
        Validity:
            Activation time: Mon 26 Aug 2024 02:12:09 AM CDT
            Expiration time: Mon 18 Nov 2024 01:12:08 AM CST
        Fingerprints:
            SHA256: 01:AF:90:6E:FC:06:5C:B5:5D:B9:55:AB:27:07:B0:E7:8C:4F:EA:46:70:67:86:A9:E0:F1:BB:F7:5A:2E:1B:64
            SHA1 (deprecated): F2:B7:9C:3C:4C:FD:57:31:37:BB:8D:F6:DD:F7:FB:A2:D7:09:B2:BD
    <-- 220 smtp.gmail.com ESMTP 8926c6da1cb9f-4d8888f9f55sm483180173.166 - gsmtp
    --> EHLO localhost
    <-- 250-smtp.gmail.com at your service, [24.152.157.105]
    <-- 250-SIZE 35882577
    <-- 250-8BITMIME
    <-- 250-AUTH LOGIN PLAIN XOAUTH2 PLAIN-CLIENTTOKEN OAUTHBEARER XOAUTH
    <-- 250-ENHANCEDSTATUSCODES
    <-- 250-PIPELINING
    <-- 250-CHUNKING
    <-- 250 SMTPUTF8
    --> AUTH PLAIN <**************deleted************************>==
    <-- 235 2.7.0 Accepted
    --> MAIL FROM:<grant.b.edwards@gmail.com>
    --> RCPT TO:<bogus>
    --> DATA
    <-- 250 2.1.0 OK 8926c6da1cb9f-4d8888f9f55sm483180173.166 - gsmtp
    <-- 553-5.1.3 The recipient address <bogus> is not a valid RFC 5321 address. For
    <-- 553-5.1.3 more information, go to
    <-- 553-5.1.3  https://support.google.com/a/answer/3221692 and review RFC 5321
    <-- 553 5.1.3 specifications. 8926c6da1cb9f-4d8888f9f55sm483180173.166 - gsmtp