[gentoo-user] [OT] sendmail relay to gmail smtp server

[Harry Putnam]

NOTE: Sorry if I've gone sort of hog wild posting this question
various places but it is a perplexing problem and I suspect there may
be help available here.  Not to mention that many groups are slow due
to Christmas holidays.

-------        ---------       ---=---       ---------      -------- 

First let me say, I'm not interested in switching mta's, just incase
someone feels like posting the usual, `hey switch to NAME OF MTA' type
post.

I want to use gmails' smtp server as Smart Host for my single user
linux box running sendmail-8.14.4

I'm hooked up to an ISP called direcpath.tv in Atlanta that uses gmail
smtp servers for its clients with addresses like reader@×××××××××.tv

They have terrible to non-existent support and no support of linux/sendmail

They use smtp.gmail.com But before I get into the extra complication
of their direcpath.tv overlay, and since I do have a normal gmail
account I thought I'd first try to get the authentication for smtp
working for that username.  hputnam3@×××××.com

So after dozens of small edits and restarts and makemaps ... cutting
to the chase:

/etc/mail/authinfo

(password obfuscated)
,----
| Athinfo:smtp.gmail.com "U:root" "I:hputnam3@×××××.com" "P:??XX??" "M: LOGIN PLAIN"
| Athinfo:smtp.gmail.com:587 "U:root" "I:hputnam3@×××××.com" "P:??XX??" "M: LOGIN PLAIN"
`----

-------        ---------       ---=---       ---------      -------- 

And I think what are the most relevant sendmail.mc settings (the whole
*mc is inlined at the end).

/etc/mail/sendmail.mc

,----
| define(`RELAY_MAILER_ARGS', `TCP $h 587')dnl
| define(`ESMTP_MAILER_ARGS', `TCP $h 587')dnl
| 
| FEATURE(`authinfo', `hash /etc/mail/authinfo')dnl 
| 
| define(`confAUTH_MECHANISMS',`EXTERNAL GSSAPI DIGEST-MD5 CRAM-MD5 LOGIN PLAIN')dnl
| TRUST_AUTH_MECH(`EXTERNAL DIGEST-MD5 CRAM-MD5 LOGIN PLAIN')dnl
| 
| define(`SMART_HOST',`smtp.gmail.com')dnl
`----

(And for the record, I did try bracketing the Smart Host like:
 define(`SMART_HOST',`[smtp.gmail.com]')dnl)

I have some old masquerade settings that I doubt are causing a
problem. I do have an account with them too.  I think the error would
be different if they were causing problems, but here those are:

(Note, that removing those only gets the same error messages)
,----
| MASQUERADE_AS(`newsguy.com')dnl
| FEATURE(`allmasquerade')dnl
| FEATURE(`masquerade_envelope')dnl
| dnl # [HP 111006_211813  Testing local_no_masquerade #]dnl
| FEATURE(`local_no_masquerade')dnl
`----

-------        ---------       ---=---       ---------      -------- 

Relevant verbose smtp logs:
,----
| 050 >>> EHLO reader.local.lan
| 050 250-mx.google.com at your service, [65.50.57.227]
| 050 250-SIZE 35882577
| 050 250-8BITMIME
| 050 250-AUTH LOGIN PLAIN XOAUTH
| 050 250 ENHANCEDSTATUSCODES
| 050 >>> MAIL From:<reader@×××××××.com> SIZE=563 AUTH=<>
| 050 530-5.5.1 Authentication Required. Learn more at                              
| 050 530 5.5.1 http://mail.google.com/support/bin/answer.py?answer=14257 py4sm63515568igc.2
`----

The `learn more' address given just above is not all that helpful.

-------        ---------       ---=---       ---------      -------- 

I think these are the sendmail logs that contain the relevant error:

(I'm not sure if the `verify=FAIL' means what it suggests)

,----
| Dec 26 21:41:38 reader sm-mta[24243]: STARTTLS=client,
| relay=smtp.gmail.com, version=TLSv1/SSLv3, verify=FAIL,
| cipher=RC4-SHA, bits=128/12
| 
| Dec 26 21:41:38 reader sm-mta[24243]: pBR2fbLX024243:
|   to=<reader@×××××××.com>, ctladdr=<reader@××××××××××××.lan>
|   (1000/1000), delay=00:00:01, xdelay=00:00:01, mailer=relay, pri=30563,
|   relay=smtp.gmail.com [209.85.225.109], dsn=5.0.0, 
|   stat=Service unavailable
| 
| Dec 26 21:41:38 reader sm-mta[24243]: pBR2fbLX024243: pBR2fbLY024243: DSN: Service unavailable
`----

-------        ---------       ---=---       ---------      -------- 

Full sendmail.mc

divert(-1)dnl
divert(0)dnl
define(`_USE_ETC_MAIL_')dnl
include(`/usr/share/sendmail/cf/m4/cf.m4')dnl
VERSIONID(`$Id: current.mc,v 1.13 2011/12/26 17:38:01 reader Exp $')
OSTYPE(`debian')dnl
DOMAIN(`debian-mta')dnl
undefine(`confHOST_STATUS_DIRECTORY')dnl        #DAEMON_HOSTSTATS=

define(`RELAY_MAILER_ARGS', `TCP $h 587')dnl
define(`ESMTP_MAILER_ARGS', `TCP $h 587')dnl
define(`PROCMAIL_MAILER_PATH',`/usr/bin/procmail')dnl

FEATURE(`authinfo', `hash /etc/mail/authinfo')dnl 
FEATURE(`access_db',`hash -T<TMPF> /etc/mail/access.db')dnl
define(`confAUTH_MECHANISMS',`EXTERNAL GSSAPI DIGEST-MD5 CRAM-MD5 LOGIN PLAIN')dnl
TRUST_AUTH_MECH(`EXTERNAL DIGEST-MD5 CRAM-MD5 LOGIN PLAIN')dnl
define(`SMART_HOST',`smtp.gmail.com')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, Addr=127.0.0.1')dnl
DAEMON_OPTIONS(`Family=inet,  Name=MSP-v4, Port=submission, M=Ea, Addr=127.0.0.1')dnl
define(`confPRIVACY_FLAGS', `needmailhelo,needexpnhelo,needvrfyhelo,restrictqrun,restrictexpand,nobodyreturn,authwarnings')dnl
define(`confCONNECTION_RATE_THROTTLE', `15')dnl
define(`confCONNECTION_RATE_WINDOW_SIZE',`10m')dnl
FEATURE(`use_cw_file')dnl
FEATURE(`greet_pause', `1000')dnl 1 seconds
FEATURE(`delay_checks', `friend', `n')dnl
define(`confBAD_RCPT_THROTTLE',`3')dnl
FEATURE(`conncontrol', `nodelay', `terminate')dnl
FEATURE(`ratecontrol', `nodelay', `terminate')dnl
include(`/etc/mail/m4/dialup.m4')dnl
include(`/etc/mail/m4/provider.m4')dnl

FEATURE(`always_add_domain')dnl
MASQUERADE_AS(`newsguy.com')dnl
FEATURE(`allmasquerade')dnl
FEATURE(`masquerade_envelope')dnl
FEATURE(`local_no_masquerade')dnl

EXPOSED_USER(`root')dnl

MAILER_DEFINITIONS
MAILER(`local')dnl
MAILER(procmail)dnl
MAILER(`smtp')dnl