[gentoo-user] Re: basic trouble with sendmail config

[Harry Putnam]

John Covici <covici@××××××××××.com> writes:

> On Sun, 04 Dec 2016 21:23:34 -0500,
> Harry Putnam wrote:
>>
>> Volker Armin Hemmann <volkerarmin@××××××××××.com> writes:
>>
>> > Am 04.12.2016 um 20:09 schrieb Harry Putnam:
>> >
>> > is there a good reason you chose sendmail over postfix? Do you hate
>> > yourself? You are a masochist?
>> >
>> > I found sendmail the worst piece of software I ever had to deal with.
>> > Windows XP user&rights management in a mixed environment with shares is
>> > delightful, writing bind config files or XFree86 configs by hand was
>> > nice, easy and a joy compared to sendmail.
>>
>> All the above.  If you are really into pain... where pulled
>> fingernails are the lowest starter level ... sendmail is something
>> I'd only dreamed about .... till now.
>>
>> OK, is there really nobody here that uses sendmail?
>>
>> I'm pretty sure the kind of immediate and complete failure I'm seeing
>> is something horribly missconfigured and might not be that much to
>> fix. If I could understand what is causing the fuss.
>
> I use it all the time with no problems.  Did you do the -X or increase
> the loglevel?

I increaded log level.. still researching about -X.

  define(`confLOG_LEVEL', `14')dnl

Now in sendmail.mc and the m4'ed product sendmail.cf

First off, I went to sendmail site downloaded the latest and compiled
from scratch. Now some of the advice in the README's about compiling
and m4 procedure actually work since stuff is in place where sendmail
expects it.  The gentoo install lacks some of the expected files and
tools. And has things in different places than un-touched sources
expect.

It appears my choice of smtp SMART HOST (smtp.gmail.com) may be
requiring STARTTLS I'm not sure how that is supposed to work my
googling seems to show a complicated process of creating certs etc etc

Anyone know how that is done for a linux box.

latest SMTP conversation and log output, followed by sendmail.mc:
-------       -------       ---=---       -------       -------
  SMTP output
-------       -------       ---=---       -------       ------- 

harry > tmail hputnam3@×××××.com
sending like this:
mailx -v -s "TEST 161205_221704 g0" hputnam3@×××××.com < /tmp/msg-161205_221704
hputnam3@×××××.com... Connecting to [127.0.0.1] via relay...
220 g0.local.lan ESMTP Sendmail 8.15.2/8.15.2; Mon, 5 Dec 2016 22:17:12 -0500
>>> EHLO g0.local.lan
250-g0.local.lan Hello g0.local.lan [127.0.0.1], pleased to meet you
250-ENHANCEDSTATUSCODES
250-PIPELINING
250-EXPN
250-VERB
250-8BITMIME
250-SIZE
250-DSN
250-ETRN
250-DELIVERBY
250 HELP
>>> VERB
250 2.0.0 Verbose mode
>>> MAIL From:<harry@××××××××.lan> SIZE=6970
250 2.1.0 <harry@××××××××.lan>... Sender ok
>>> RCPT To:<hputnam3@×××××.com>
>>> DATA
250 2.1.5 <hputnam3@×××××.com>... Recipient ok
354 Enter mail, end with "." on a line by itself
>>> .
050 <hputnam3@×××××.com>... Connecting to gmail-smtp-msa.l.google.com. port 587 via relay...
050 220 smtp.gmail.com ESMTP m136sm7913890ywd.19 - gsmtp
050 >>> EHLO g0.local.lan
050 250-smtp.gmail.com at your service, [76.97.132.53]
050 250-SIZE 35882577
050 250-8BITMIME
050 250-STARTTLS
050 250-ENHANCEDSTATUSCODES
050 250-PIPELINING
050 250-CHUNKING
050 250 SMTPUTF8
050 >>> MAIL From:<harry@×××××××.com> SIZE=7234
050 530 5.7.0 Must issue a STARTTLS command first. m136sm7913890ywd.19 - gsmtp
050 <harry@××××××××.lan>... Connecting to local...
250 2.0.0 uB63HCsI003822 Message accepted for delivery
hputnam3@×××××.com... Sent (uB63HCsI003822 Message accepted for delivery)
Closing connection to [127.0.0.1]
>>> QUIT
221 2.0.0 g0.local.lan closing connection

-------       -------       ---=---       -------       -------
/var/log/mail.log output (formatted for email):
-------       -------       ---=---       -------       -------

Dec  5 22:17:12 g0 sendmail[3821]: uB63H7Ew003821: from=harry,
size=6970, class=0, nrcpts=1,
msgid=<201612060317.uB63H7Ew003821@××××××××.lan>,
relay=harry@localhost

Dec 5 22:17:12 g0 sm-mta[3822]: NOQUEUE: connect from g0.local.lan
[127.0.0.1]

Dec 5 22:17:12 g0 sm-mta[3822]: uB63HCsI003822: Milter: no active
filter

Dec 5 22:17:13 g0 sm-mta[3822]: uB63HCsI003822:
from=<harry@××××××××.lan>, size=7234, class=0, nrcpts=1,
msgid=<201612060317.uB63H7Ew003821@××××××××.lan>, proto=ESMTP,
daemon=MTA-v4, relay=g0.local.lan [127.0.0.1]

Dec 5 22:17:13 g0 sm-mta[3822]: uB63HCsI003822: SMTP outgoing connect
on g0.local.lan

Dec 5 22:17:13 g0 sm-mta[3822]: uB63HCsI003822:
to=<hputnam3@×××××.com>, ctladdr=<harry@××××××××.lan> (1000/1050),
delay=00:00:00, xdelay=00:00:00, mailer=relay, pri=37234,
relay=gmail-smtp-msa.l.google.com. [74.125.21.109], dsn=5.0.0,
stat=Service unavailable

Dec 5 22:17:13 g0 sm-mta[3822]: uB63HCsI003822: uB63HCsJ003822: DSN:
Service unavailable

Dec 5 22:17:13 g0 sm-mta[3823]: uB63HCsJ003822: Warning: program
/usr/bin/procmail unsafe: No such file or directory

Dec 5 22:17:13 g0 sm-mta[3823]: uB63HCsJ003822: SYSERR(root): Cannot
exec /usr/bin/procmail: No such file or directory

Dec 5 22:17:13 g0 sm-mta[3822]: uB63HCsJ003822:
to=<harry@××××××××.lan>, delay=00:00:00, xdelay=00:00:00,
mailer=local, pri=38258, dsn=4.0.0, stat=Operating system error

Dec 5 22:17:13 g0 sm-mta[3822]: uB63HCsI003822: done; delay=00:00:00,
ntries=1

Dec 5 22:17:13 g0 sendmail[3821]: uB63H7Ew003821:
to=hputnam3@×××××.com, ctladdr=harry (1000/1050), delay=00:00:06,
xdelay=00:00:01, mailer=relay, pri=36970, relay=[127.0.0.1]
[127.0.0.1], dsn=2.0.0, stat=Sent (uB63HCsI003822 Message accepted for
delivery)

-------       -------       ---=---       -------       -------
sendmail.mc
-------       -------       ---=---       -------       ------- 

  divert(-1)dnl
  divert(0)dnl
  include(`/usr/local/src/sendmail-8.15.2/cf/m4/cf.m4')dnl
  VERSIONID(`$Id: sendmail.mc,v 1.20 2016/12/04 16:17:08 g0 Exp $')
  OSTYPE(`linux')dnl
  DOMAIN(`generic')dnl
  define(`confLOG_LEVEL', `14')dnl
  define(`PROCMAIL_MAILER_PATH',`/usr/bin/procmail')dnl
  define(`confAUTH_MECHANISMS',`LOGIN PLAIN')dnl
  FEATURE(`access_db',`hash -T<TMPF> /etc/mail/access.db')dnl
  FEATURE(`no_default_msa')dnl
  DAEMON_OPTIONS(`Family=inet,  Name=MTA-v4, Port=smtp')dnl
  DAEMON_OPTIONS(`Family=inet,  Name=MSP-v4, Port=submission, M=Ea')dnl
  define(`confCONNECTION_RATE_THROTTLE', `15')dnl
  define(`confCONNECTION_RATE_WINDOW_SIZE',`10m')dnl
  FEATURE(`greet_pause', `1000')dnl 1 seconds
  FEATURE(`delay_checks', `friend', `n')dnl
  FEATURE(`conncontrol', `nodelay', `terminate')dnl
  FEATURE(`ratecontrol', `nodelay', `terminate')dnl
  FEATURE(`always_add_domain')dnl
  MASQUERADE_AS(`newsguy.com')dnl
  FEATURE(`allmasquerade')dnl
  FEATURE(`masquerade_envelope')dnl
  FEATURE(`local_no_masquerade')dnl
  FEATURE(`smrsh')dnl
  MAILER_DEFINITIONS
  define(`SMART_HOST',`[smtp.gmail.com]')dnl
  define(`RELAY_MAILER_ARGS', `TCP $h 587')dnl
  define(`ESMTP_MAILER_ARGS', `TCP $h 587')dnl
  FEATURE(`authinfo', `hash /etc/mail/authinfo')dnl
  MAILER(`local')dnl
  MAILER(procmail)dnl
  MAILER(`smtp')dnl