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

[Harry Putnam]

John Covici  writes:

> Well, you have several issues, looks like procmail executable does not
> have correct permissions, should be
> -rwsr-s--x 1 root root
> or at least this is the way I have it.

The issue with procmail was that it was not even installed... Suprised
me at first but this is a rather new install and hadn't gotten that
done yet.

Anyway, once emerged /usr/bin/procmail has the same permissions as you posted.

> If you need to send out on port 587, you need to enable starttls by
> generating a cert, or getting one from somewhere, defining the
> mechanisms and other things.  I think once you get that done things
> will work, or you will be able to figure it out easily.

For anyone stumbling on this thread looking for sendmail info I post
the following, and to conclude our thread.

I see the sendmail sources do have CACerts file in top level of the
unpacked sources.  Maybe that is what folks use.  Also there is some
explanation in one of the READMEs as well but still was not at all
clear what really needed doing but actually:

I dodged the issue altogether and swiched my smart host from
smtp.gmail.com (which demands STARTTLS) to smtp.newsguy.com.  So when
sending to a gmail address now newsguy takes care of whatever it is
with Certs.

Should have tried that sooner... but there was enough other stuff
wrong that probably wouldn't have worked yet anyway.

All working for now. Sending works, even to gmail addresses.  And
others work.  Logs show no problems.

Thanks for the help.

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

[John Covici]

On Mon, 05 Dec 2016 22:26:33 -0500,
Harry Putnam wrote:
> 
> John Covici  writes:
> 
> > On Sun, 04 Dec 2016 21:23:34 -0500,
> > Harry Putnam wrote:
> >> 
> >> Volker Armin Hemmann  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 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 hputn...@gmail.com
> sending like this:
> mailx -v -s "TEST 161205_221704 g0" hputn...@gmail.com < 
> /tmp/msg-161205_221704
> hputn...@gmail.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: SIZE=6970
> 250 2.1.0 ... Sender ok
> >>> RCPT To:
> >>> DATA
> 250 2.1.5 ... Recipient ok
> 354 Enter mail, end with "." on a line by itself
> >>> .
> 050 ... 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: SIZE=7234
> 050 530 5.7.0 Must issue a STARTTLS command first. m136sm7913890ywd.19 - gsmtp
> 050 ... Connecting to local...
> 250 2.0.0 uB63HCsI003822 Message accepted for delivery
> hputn...@gmail.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.ub63h7ew003...@g0.local.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=, size=7234, class=0, nrcpts=1,
> msgid=<201612060317.ub63h7ew003...@g0.local.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=, ctladdr= (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 

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

[Harry Putnam]

John Covici  writes:

> On Sun, 04 Dec 2016 21:23:34 -0500,
> Harry Putnam wrote:
>> 
>> Volker Armin Hemmann  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 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 hputn...@gmail.com
sending like this:
mailx -v -s "TEST 161205_221704 g0" hputn...@gmail.com < /tmp/msg-161205_221704
hputn...@gmail.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: SIZE=6970
250 2.1.0 ... Sender ok
>>> RCPT To:
>>> DATA
250 2.1.5 ... Recipient ok
354 Enter mail, end with "." on a line by itself
>>> .
050 ... 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: SIZE=7234
050 530 5.7.0 Must issue a STARTTLS command first. m136sm7913890ywd.19 - gsmtp
050 ... Connecting to local...
250 2.0.0 uB63HCsI003822 Message accepted for delivery
hputn...@gmail.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.ub63h7ew003...@g0.local.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=, size=7234, class=0, nrcpts=1,
msgid=<201612060317.ub63h7ew003...@g0.local.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=, ctladdr= (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 

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

[Mick]

On Sunday 04 Dec 2016 21:28:06 John Covici wrote:
> On Sun, 04 Dec 2016 21:23:34 -0500,
> 
> Harry Putnam wrote:
> > Volker Armin Hemmann  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 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?

What John said.  In addition, pay particular attention both to ownership and 
access rights for sendmail directories and config files.  They should not be 
world accessible for obvious security reasons and in addition access.db and  
aliases.db files should be owned by root.
-- 
Regards,
Mick

signature.asc
Description: This is a digitally signed message part.

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

[John Covici]

On Sun, 04 Dec 2016 21:23:34 -0500,
Harry Putnam wrote:
> 
> Volker Armin Hemmann  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 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?

-- 
Your life is like a penny.  You're going to lose it.  The question is:
How do
you spend it?

 John Covici
 cov...@ccs.covici.com

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

[Harry Putnam]

Volker Armin Hemmann  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 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.

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

[Harry Putnam]

"J. Roeleveld"  writes:

[...]

> I stopped using sendmail when easier to configure alternatives came along. 
> Currently using Postfix.
>
> As such, I can't help in checking your config. But I do remember you
> had to compile the config files into a format sendmail actually can
> read. Did you do that part?

Yes
I m4'ed as explained in /usr/share/sendmail-cf/README

I didn't post the *.cf files because the sendmail.cf if very long and
not all that readable... and anyway what is in it is a direct result
of what is in sendmail.mc

I'm adding another piece of the output puzzle from /var/log/mail.log

  Dec 4 15:44:58 g0 sm-cm[8151]: uB4J3YBB003855:
  to=hputn...@gmail.com, ctladdr=harry (1000/1050), delay=01:41:24,
  xdelay=00:00:00, mailer=relay, pri=936804, relay=[127.0.0.1],
  dsn=4.0.0, stat=Deferred: 451 4.3.0 Temporary system failure. Please
  try again later.