updated my instances and you're right, we have introduced a regression at
some point

it'll be fixed in next snapshot

Gilles


On Sun, Jul 14, 2013 at 04:49:23AM -0300, Hugo Osvaldo Barrera wrote:
> On 2013-07-13 23:57, Gilles Chehade wrote:
> > On Fri, Jul 12, 2013 at 02:20:47PM -0300, Hugo Osvaldo Barrera wrote:
> > > 
> > > Hmmm... It's odd, because it looks like smtpd isn't using TLS when
> > > relaying my local email.
> > > Let me explain a bit.
> > > 
> > > [...]
> > >
> > 
> > Can you include the output of 'smtpd -dv' as the daemon starts and until
> > it stabilizes ?
> > 
> > It's hard to debug without that information, but it TLS should work fine
> > as I used it daily on both OpenBSD and Linux Debian.
> > 
> > 
> > > I understand that the first part (mutt->smtpd) doesn't run TLS; because
> > > my local instance doesn't listen with TLS, but shouldn't the email be
> > > relayed using TLS (local smtpd->remote smtpd)?
> > >
> > 
> > Yes, unless you explicitely require no encryption or smtps using one of
> > the following:
> > 
> >      relay via smtp://
> >      relay via smtps://
> > 
> > TLS is always attempted first.
> > 
> > 
> > > Emails from EXTERNAL hosts seem to be using TLS, and, from the looks of
> > > the logs, my local smtpd isn't trying to use STARTTLS at any given moment.
> > > 
> > > Is this a bug? Shouldn't smtpd always try to use TLS on outgoing email?
> > > 
> > 
> > Logs needed
> > 
> > 
> > -- 
> > Gilles Chehade
> > 
> > https://www.poolp.org                                          @poolpOrg
> > 
> > -- 
> > You received this email because you are subscribed to the 
> > "[email protected]" list
> > To unsubscribe, send mail with subject: [[email protected]] unregister
> 
> Full log of the receiving server (the MX server for the email's
> recipient):
> 
> # smtpd -dv 
> info: OpenSMTPD 201307121003 starting
> debug: bounce warning after 4h
> debug: using "fs" queue backend
> debug: using "ramqueue" scheduler backend
> debug: using "ram" stat backend
> info: startup [debug mode]
> debug: init server-ssl tree
> info: No CA found in /etc/mail/certs/egress.ca
> info: No DH parameters found in /etc/mail/certs/egress.dh: using built-in 
> parameters
> debug: init client-ssl tree
> debug: parent_send_config_ruleset: reloading
> debug: parent_send_config_mfa: reloading
> debug: parent_send_config: configuring smtp
> queue: queue encryption enabled
> debug: queue: done loading queue into scheduler
> debug: mfa ready
> debug: smtp: listen on IPv6:2607:f2f8:a520::2 port 587 flags 0x69 cert 
> "egress"
> debug: smtp: listen on IPv6:fe80::5054:ff:fe27:2425%em0 port 587 flags 0x69 
> cert "egress"
> debug: smtp: listen on 174.136.104.18 port 587 flags 0x69 cert "egress"
> debug: smtp: listen on IPv6:2607:f2f8:a520::2 port 465 flags 0x2 cert "egress"
> debug: smtp: listen on IPv6:fe80::5054:ff:fe27:2425%em0 port 465 flags 0x2 
> cert "egress"
> debug: smtp: listen on 174.136.104.18 port 465 flags 0x2 cert "egress"
> debug: smtp: listen on IPv6:2607:f2f8:a520::2 port 25 flags 0x1 cert "egress"
> debug: smtp: listen on IPv6:fe80::5054:ff:fe27:2425%em0 port 25 flags 0x1 
> cert "egress"
> debug: smtp: listen on 174.136.104.18 port 25 flags 0x1 cert "egress"
> debug: smtp: listen on 127.0.0.1 port 10028 flags 0x0 cert ""
> debug: smtp: listen on IPv6:fe80::1%lo0 port 10028 flags 0x0 cert ""
> debug: smtp: listen on IPv6:::1 port 10028 flags 0x0 cert ""
> debug: smtp: listen on 127.0.0.1 port 25 flags 0x0 cert ""
> debug: smtp: listen on IPv6:fe80::1%lo0 port 25 flags 0x0 cert ""
> debug: smtp: listen on IPv6:::1 port 25 flags 0x0 cert ""
> debug: smtp: will accept at most 495 clients
> debug: smtpd: scanning offline queue...
> debug: smtpd: offline scanning done
> debug: smtp: new client on listener: 0xe24a6224120
> smtp-in: New session 000000009c3401ae from host hyperion.ubertech.com.ar 
> [190.210.108.249]
> debug: aliases_virtual_get: '[email protected]' resolved to 1 nodes
> debug: 0xe24aee5f000: end of message, msgflags=0x0000
> smtp-in: Accepted message 8e914422 on session 000000009c3401ae: 
> from=<[email protected]>, to=<[email protected]>, 
> size=1381, ndest=1, proto=ESMTP
> debug: scheduler: evp:8e914422a6e35b71 scheduled (mda)
> debug: lka: userinfo <getpwnam>:hugo
> debug: mda: new session 00000000473a1560 for user "hugo" evpid 
> 8e914422a6e35b71
> debug: mda: no more envelope for "hugo"
> debug: mda: got message fd 3 for session 00000000473a1560 evpid 
> 8e914422a6e35b71
> debug: mda: querying mda fd for session 00000000473a1560 evpid 
> 8e914422a6e35b71
> debug: smtpd: forking mda for session 00000000473a1560: 
> "/usr/local/libexec/dovecot/dovecot-lda -d [email protected]" as hugo
> debug: mda: got mda fd 4 for session 00000000473a1560 evpid 8e914422a6e35b71
> debug: mda: end-of-file for session 00000000473a1560 evpid 8e914422a6e35b71
> debug: mda: all data sent for session 00000000473a1560 evpid 8e914422a6e35b71
> debug: smtpd: mda process done for session 00000000473a1560: exited okay
> delivery: Ok for 8e914422a6e35b71: from=<[email protected]>, 
> to=<[email protected]>, user=hugo, method=mda, delay=1s, 
> stat=Delivered
> debug: mda: session 00000000473a1560 done
> debug: mda: user "hugo" becomes runnable
> debug: mda: all done for user "hugo"
> smtp-in: Closing session 000000009c3401ae
> debug: smtp: 0xe24aee5f000: deleting session: done
> 
> # cat /etc/mail/smtpd.conf:
> # This is the smtpd server system-wide configuration file.
> # See smtpd.conf(5) for more information.
> 
> queue encryption key xxx
> 
> table usrs db:/etc/mail/users.db
> table aliases db:/etc/mail/aliases.db
> table domains db:/etc/mail/domains.db
> 
> listen on lo0
> listen on lo0 port 10028 tag DKIM
> listen on egress port  25 tls                     hostname 
> "mx1.ubertech.com.ar"
> listen on egress port 465 smtps                   hostname 
> "smtp.ubertech.com.ar" # Obsoleted by RFC3207
> listen on egress port 587 tls-require auth <usrs> hostname 
> "smtp.ubertech.com.ar"
> 
> table catchall { "@" => hugo }
> 
> accept from any for local            alias <aliases>    deliver to mda 
> "/usr/local/libexec/dovecot/dovecot-lda -d [email protected]"
> accept from any for domain <domains> virtual <catchall> deliver to mda 
> "/usr/local/libexec/dovecot/dovecot-lda -d [email protected]"
> 
> accept tagged DKIM for any relay
> accept for any relay via smtp://127.0.0.1:10027
> 
> ###
> Full log of the relaying instance of smtpd (the one running on my
> desktop):
> 
> # smtpd -dv
> info: OpenSMTPD 201307121003p1 starting
> debug: bounce warning after 4h
> debug: using "fs" queue backend
> debug: using "ramqueue" scheduler backend
> debug: using "ram" stat backend
> info: startup [debug mode]
> debug: init server-ssl tree
> debug: init client-ssl tree
> libevent 2.0.21-stable (epoll)
> debug: parent_send_config_ruleset: reloading
> debug: parent_send_config_mfa: reloading
> debug: parent_send_config: configuring smtp
> debug: mfa ready
> debug: smtp: listen on 127.0.0.1 port 25 flags 0x0 cert ""
> debug: smtp: will accept at most 2022 clients
> debug: queue: done loading queue into scheduler
> debug: smtpd: scanning offline queue...
> debug: smtpd: offline scanning done
> debug: smtp: new client on listener: 0x23181f0
> [warn] event_del: event has no event_base set.
> smtp-in: New session 00000000b7e69da4 from host localhost.localdomain 
> [127.0.0.1]
> debug: 0x236a7e0: end of message, msgflags=0x0000
> smtp-in: Accepted message b7e69da4 on session 00000000b7e69da4: 
> from=<[email protected]>, to=<[email protected]>, 
> size=1165, ndest=1, proto=ESMTP
> debug: scheduler: evp:b7e69da42d74027d scheduled (mta)
> smtp-in: Closing session 00000000b7e69da4
> debug: smtp: 0x236a7e0: deleting session: done
> debug: mta: received evp:b7e69da42d74027d for <[email protected]>
> debug: mta: draining [relay:osvaldobarrera.com.ar] refcount=1, ntask=1, 
> nconnector=0, nconn=0
> debug: mta: querying MX for [relay:osvaldobarrera.com.ar]...
> debug: mta: [relay:osvaldobarrera.com.ar] waiting for MX
> debug: MXs for domain osvaldobarrera.com.ar:
>     IPv6:2607:f2f8:a520::2 preference 0
>     174.136.104.18 preference 0
>     190.210.108.249 preference 10
> debug: mta: ... got mx (0x23174e0, osvaldobarrera.com.ar, 
> [relay:osvaldobarrera.com.ar])
> debug: mta: draining [relay:osvaldobarrera.com.ar] refcount=1, ntask=1, 
> nconnector=0, nconn=0
> debug: mta: querying source for [relay:osvaldobarrera.com.ar]...
> debug: mta: ... got source for [relay:osvaldobarrera.com.ar]: []
> debug: mta: new [connector:[]->[relay:osvaldobarrera.com.ar],0x1000]
> debug: mta: connecting with [connector:[]->[relay:osvaldobarrera.com.ar],0x0]
> debug: mta-routing: searching new route for 
> [connector:[]->[relay:osvaldobarrera.com.ar],0x0]...
> debug: mta-routing: selecting candidate route [] <-> IPv6:2607:f2f8:a520::2
> debug: mta-routing: skipping route [] <-> 174.136.104.18: current one is 
> better
> debug: mta: ma_route_unref(): really discarding route [] <-> 174.136.104.18
> debug: mta-routing: spawning new connection on [] <-> IPv6:2607:f2f8:a520::2
> debug: mta: 0x235a680: spawned for relay [relay:osvaldobarrera.com.ar]
> debug: mta: connecting with [connector:[]->[relay:osvaldobarrera.com.ar],0x0]
> debug: mta: cannot use [relay:osvaldobarrera.com.ar] before 2s
> debug: mta-routing: no route available for 
> [connector:[]->[relay:osvaldobarrera.com.ar],0x0]: must wait a bit
> debug: mta: retrying to connect on 
> [connector:[]->[relay:osvaldobarrera.com.ar],0x0] in 2s...
> debug: mta: draining [relay:osvaldobarrera.com.ar] refcount=3, ntask=1, 
> nconnector=1, nconn=1
> debug: mta: scheduling relay [relay:osvaldobarrera.com.ar] in 1s...
> [warn] event_del: event has no event_base set.
> smtp-out: Connecting to smtp://IPv6:2607:f2f8:a520::2:25 (2607:f2f8:a520::2) 
> on session 0000000209c3fb3b...
> debug: mta: io_connect failed: Network is unreachable
> smtp-out: Error on session 0000000209c3fb3b: Connection failed: Network is 
> unreachable
> debug: mta: 0x235a680: session done
> [warn] event_del: event has no event_base set.
> debug: mta_route_collect([] <-> IPv6:2607:f2f8:a520::2 (2607:f2f8:a520::2))
> smtp-out: Disabling route [] <-> IPv6:2607:f2f8:a520::2 (2607:f2f8:a520::2) 
> for 800s
> debug: mta: connecting with 
> [connector:[]->[relay:osvaldobarrera.com.ar],0x2000]
> debug: mta: canceling connector timeout
> debug: mta: cannot use [relay:osvaldobarrera.com.ar] before 2s
> debug: mta-routing: no route available for 
> [connector:[]->[relay:osvaldobarrera.com.ar],0x2000]: must wait a bit
> debug: mta: retrying to connect on 
> [connector:[]->[relay:osvaldobarrera.com.ar],0x2000] in 2s...
> debug: mta: ... timeout for [relay:osvaldobarrera.com.ar]
> debug: mta: draining [relay:osvaldobarrera.com.ar] refcount=1, ntask=1, 
> nconnector=1, nconn=0
> debug: mta: querying source for [relay:osvaldobarrera.com.ar]...
> debug: mta: ... got source for [relay:osvaldobarrera.com.ar]: []
> debug: mta: connecting with 
> [connector:[]->[relay:osvaldobarrera.com.ar],0x2000]
> debug: mta: canceling connector timeout
> debug: mta: cannot use [relay:osvaldobarrera.com.ar] before 1s
> debug: mta-routing: no route available for 
> [connector:[]->[relay:osvaldobarrera.com.ar],0x2000]: must wait a bit
> debug: mta: retrying to connect on 
> [connector:[]->[relay:osvaldobarrera.com.ar],0x2000] in 1s...
> debug: mta: draining [relay:osvaldobarrera.com.ar] refcount=2, ntask=1, 
> nconnector=1, nconn=0
> debug: mta: scheduling relay [relay:osvaldobarrera.com.ar] in 10s...
> debug: mta: ... timeout for 
> [connector:[]->[relay:osvaldobarrera.com.ar],0x2000]
> debug: mta: connecting with [connector:[]->[relay:osvaldobarrera.com.ar],0x0]
> debug: mta-routing: searching new route for 
> [connector:[]->[relay:osvaldobarrera.com.ar],0x0]...
> debug: mta-routing: skipping route [] <-> IPv6:2607:f2f8:a520::2 
> (2607:f2f8:a520::2): suspend
> debug: mta-routing: selecting candidate route [] <-> 174.136.104.18
> debug: mta-routing: spawning new connection on [] <-> 174.136.104.18
> debug: mta: 0x235a680: spawned for relay [relay:osvaldobarrera.com.ar]
> debug: mta: connecting with [connector:[]->[relay:osvaldobarrera.com.ar],0x0]
> debug: mta: cannot use [relay:osvaldobarrera.com.ar] before 2s
> debug: mta-routing: no route available for 
> [connector:[]->[relay:osvaldobarrera.com.ar],0x0]: must wait a bit
> debug: mta: retrying to connect on 
> [connector:[]->[relay:osvaldobarrera.com.ar],0x0] in 2s...
> [warn] event_del: event has no event_base set.
> smtp-out: Connecting to smtp://174.136.104.18:25 (174.136.104.18) on session 
> 00000003ed5921eb...
> [warn] event_del: event has no event_base set.
> smtp-out: Connected on session 00000003ed5921eb
> debug: mta-routing: route [] <-> 174.136.104.18 (174.136.104.18) is now valid.
> debug: mta: connecting with 
> [connector:[]->[relay:osvaldobarrera.com.ar],0x2000]
> debug: mta: canceling connector timeout
> debug: mta: enough connections already
> debug: mta: 0x235a680: handling next task for relay 
> [relay:osvaldobarrera.com.ar]
> relay: Ok for b7e69da42d74027d: session=00000003ed5921eb, 
> from=<[email protected]>, to=<[email protected]>, rcpt=<->, 
> source=172.16.8.7, relay=174.136.104.18 (174.136.104.18), delay=5s, stat=250 
> 8e914422 Message accepted for delivery
> debug: mta: waiting for 1s before next transaction
> mta: timeout for session hangon
> debug: mta: 0x235a680: no task for relay [relay:osvaldobarrera.com.ar]
> mta: debug: last connection: hanging on for 9s
> mta: timeout for session hangon
> debug: mta: 0x235a680: no task for relay [relay:osvaldobarrera.com.ar]
> mta: debug: last connection: hanging on for 8s
> mta: timeout for session hangon
> debug: mta: 0x235a680: no task for relay [relay:osvaldobarrera.com.ar]
> mta: debug: last connection: hanging on for 7s
> mta: timeout for session hangon
> debug: mta: 0x235a680: no task for relay [relay:osvaldobarrera.com.ar]
> mta: debug: last connection: hanging on for 6s
> mta: timeout for session hangon
> debug: mta: 0x235a680: no task for relay [relay:osvaldobarrera.com.ar]
> mta: debug: last connection: hanging on for 5s
> mta: timeout for session hangon
> debug: mta: 0x235a680: no task for relay [relay:osvaldobarrera.com.ar]
> mta: debug: last connection: hanging on for 4s
> debug: mta: ... timeout for [relay:osvaldobarrera.com.ar]
> debug: mta: draining [relay:osvaldobarrera.com.ar] refcount=2, ntask=0, 
> nconnector=1, nconn=1
> debug: mta: all done for [relay:osvaldobarrera.com.ar]
> mta: timeout for session hangon
> debug: mta: 0x235a680: no task for relay [relay:osvaldobarrera.com.ar]
> mta: debug: last connection: hanging on for 3s
> mta: timeout for session hangon
> debug: mta: 0x235a680: no task for relay [relay:osvaldobarrera.com.ar]
> mta: debug: last connection: hanging on for 2s
> mta: timeout for session hangon
> debug: mta: 0x235a680: no task for relay [relay:osvaldobarrera.com.ar]
> mta: debug: last connection: hanging on for 1s
> mta: timeout for session hangon
> debug: mta: 0x235a680: no task for relay [relay:osvaldobarrera.com.ar]
> smtp-out: Closing session 00000003ed5921eb: 1 message sent.
> debug: mta: 0x235a680: session done
> debug: mta_route_collect([] <-> 174.136.104.18 (174.136.104.18))
> debug: mta: connecting with 
> [connector:[]->[relay:osvaldobarrera.com.ar],0x2000]
> debug: mta: canceling connector timeout
> debug: mta: no task for connector
> debug: mta: ma_route_unref(): really discarding route [] <-> 174.136.104.18 
> (174.136.104.18)
> debug: mta: freeing [relay:osvaldobarrera.com.ar]
> debug: mta: freeing [connector:[]->[relay:osvaldobarrera.com.ar],0x2000]
> debug: mta: canceling timeout for 
> [connector:[]->[relay:osvaldobarrera.com.ar],0x2000]
> 
> # cat /etc/mail/smtpd.conf
> listen on lo
> accept from local for any relay
> 
> ###
> 
> As far as I can see, no attempt is being made to use TLS at any point.
> In case it's revelant; my desktop runs ArchLinux, the server is OpenBSD 5.3.
> 
> Thanks,
> 
> -- 
> Hugo Osvaldo Barrera



-- 
Gilles Chehade

https://www.poolp.org                                          @poolpOrg

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