help with SMTP AUTH

[Anton Shterenlikht]

Please help set up sendmail SMTP AUTH.

I'm on FreeBSD 11.0-RELEASE-p9 with
sendmail 8.15.2 installed via mail/sendmail:

# pkg info -xo send
sendmail+tls+sasl2-8.15.2_3 mail/sendmail
#

# sendmail -d0,1 < /dev/null
Version 8.15.2
Compiled with: DNSMAP IPV6_FULL LOG MAP_REGEX MATCHGECOS MILTER
MIME7TO8 MIME8TO7 NAMED_BIND NETINET NETINET6 NETUNIX NEWDB NIS
PICKY_HELO_CHECK PIPELINING SASLv2 SCANF STARTTLS TCPWRAPPERS
USERDB XDEBUG

so sendmail is built with SASLv2 and STARTTLS

I follow http://www.sendmail.org/~ca/email/auth.html#smtpclient
"Using sendmail as a client with AUTH"

I have:

# cat /etc/mail/auth/client-info
AuthInfo:smtp.office365.com "U:me...@bristol.ac.uk" "I:me...@bristol.ac.uk" "P:<my passwd>"

Q1: Is the ISP name ok without a port,
or should I use smtp.office365.com:587 ?

I've run

# makemap hash client-info < client-info

I added these lines to freebsd.mc:

dnl set SASL options
TRUST_AUTH_MECH(`GSSAPI DIGEST-MD5 CRAM-MD5 LOGIN')dnl
define(`confAUTH_MECHANISMS', `GSSAPI DIGEST-MD5 CRAM-MD5 LOGIN')dnl
define(`SMART_HOST', `smtp.office365.com')dnl
FEATURE(`authinfo',`hash /etc/mail/auth/client-info')dnl

Q2. Does port 587 need to be specified in SMART_HOST?

Then

# make all install restart

Q3. Do "user open" fields in ps -axwwdd indicate a problem?

# ps -axwwdd
*skip*
93786 - Is 0:00.00 |-- sendmail: ./v6ACqKa4093217 smtp.office365.com: user open (sendmail)
93909 - Is 0:00.00 |-- sendmail: Queue runner@00:30:00 for /var/spool/clientmqueue (sendmail)
93911 - Ss 0:00.00 |-- sendmail: accepting connections (sendmail)
93912 - S 0:00.00 | `-- sendmail: ./v6ACMbKQ092046 smtp.office365.com: user open (sendmail)
93917 - Is 0:00.00 |-- sendmail: Queue runner@00:01:00 for /var/spool/mqueue (sendmail)
93918 - I 0:00.00 | `-- sendmail: ./v6ACF9Bo091887 smtp.office365.com: user open (sendmail)


There doesn't seem to be any indication
of errors in /var/log/maillog.

# mailq
/var/spool/mqueue (11 requests)
-----Q-ID----- --Size-- -----Q-Time----- ------------Sender/Recipient-----------
v6ADgB0k093947* 0 Mon Jul 10 14:42 <me...@mech-as222.men.bris.ac.uk>
<me...@bris.ac.uk>
v6ACqKa4093217* 0 Mon Jul 10 13:52 <me...@mech-as222.men.bris.ac.uk>
(Deferred: Operation timed out with smtp.office365.com)
<me...@bris.ac.uk>
*skip*

Please advise

Thanks

Anton

[Andrea Venturoli]

On 07/10/17 15:44, Anton Shterenlikht wrote:
> Please help set up sendmail SMTP AUTH.

Disclaimer: I'm not sure how to do what you want to do, but I've seen
your messages in several places with no other answers, so I'll try...

> I have:
>
> # cat /etc/mail/auth/client-info
> AuthInfo:smtp.office365.com "U:me...@bristol.ac.uk" "I:me...@bristol.ac.uk" "P:<my passwd>"
>
> Q1: Is the ISP name ok without a port,
> or should I use smtp.office365.com:587 ?

I don't think you can/should put the port in the authinfo file.

> Q2. Does port 587 need to be specified in SMART_HOST?

I don't think you can do this either.

See
> https://unix.stackexchange.com/questions/132711/using-port-587-with-sendmail

(I haven't tried this).




bye

[Anton Shterenlikht]

Andrea Venturoli <ml.die...@netfence.it> writes:

>See
>> https://unix.stackexchange.com/questions/132711/using-port-587-with-sendmail

I actually saw this before, but read it again, and
yes, this is the miracle line:

define(`RELAY_MAILER_ARGS', `TCP $h 587')dnl

Now works fine.

Thanks!

Anton