I have been using opensmtp on gentoo linux for some time, but lately
relaying to GMail lis not working.

The current version of opensmtp is 6.0.2p1.

The log file of running

# smtpd -vd 2>&1 | tee /var/tmp/smtpd.log

and send a message with the command

$ MSG="Test #43" && echo "$MSG" | mutt -s "$MSG" malaqu...@gmail.com
romi...@operamail.com

is attached.

Any help in solving this issue is welcome.

Romildo
debug: init ssl-tree
debug: init ca-tree
debug: init ssl-tree
debug: using "fs" queue backend
debug: using "ramqueue" scheduler backend
debug: using "ram" stat backend
info: OpenSMTPD 6.0.2p1 starting
debug: init ssl-tree
debug: init ca-tree
debug: init ssl-tree
debug: using "fs" queue backend
debug: using "ramqueue" scheduler backend
debug: using "ram" stat backend
setup_peer: klondike -> control[16050] fd=4
setup_peer: klondike -> pony express[16052] fd=5
setup_proc: klondike done
setup_done: ca[16049] done
debug: init ssl-tree
debug: init ssl-tree
debug: init ca-tree
debug: init ssl-tree
debug: using "fs" queue backend
debug: using "ramqueue" scheduler backend
debug: using "ram" stat backend
debug: init ca-tree
debug: init ssl-tree
debug: using "fs" queue backend
debug: using "ramqueue" scheduler backend
debug: using "ram" stat backend
setup_peer: lookup -> control[16050] fd=6
setup_peer: control -> klondike[16049] fd=5
setup_peer: lookup -> pony express[16052] fd=7
setup_peer: lookup -> queue[16053] fd=8
setup_peer: control -> lookup[16051] fd=6
setup_peer: control -> pony express[16052] fd=7
setup_peer: control -> queue[16053] fd=8
setup_peer: control -> scheduler[16054] fd=9
setup_proc: control done
setup_done: control[16050] done
setup_proc: lookup done
setup_done: lka[16051] done
debug: init ssl-tree
debug: init ca-tree
debug: init ssl-tree
debug: using "fs" queue backend
debug: using "ramqueue" scheduler backend
debug: using "ram" stat backend
debug: init ssl-tree
debug: init ca-tree
debug: init ssl-tree
setup_peer: queue -> control[16050] fd=8
debug: using "fs" queue backend
debug: using "ramqueue" scheduler backend
debug: using "ram" stat backend
debug: init ssl-tree
debug: init ca-tree
setup_peer: pony express -> control[16050] fd=7
setup_peer: queue -> pony express[16052] fd=9
debug: init ssl-tree
debug: using "fs" queue backend
debug: using "ramqueue" scheduler backend
debug: using "ram" stat backend
setup_peer: pony express -> klondike[16049] fd=8
setup_peer: queue -> lookup[16051] fd=10
setup_peer: pony express -> lookup[16051] fd=9
setup_peer: queue -> scheduler[16054] fd=11
setup_peer: scheduler -> control[16050] fd=9
setup_peer: pony express -> queue[16053] fd=10
setup_peer: scheduler -> queue[16053] fd=10
setup_proc: pony express done
filter: building simple chains...
setup_done: pony[16052] done
filter: building complex chains...
filter: done building complex chains
setup_proc: queue done
setup_done: queue[16053] done
setup_proc: scheduler done
debug: bounce warning after 4h
setup_done: scheduler[16054] done
smtpd: setup done
debug: ca_engine_init: using RSA privsep engine
debug: parent_send_config_ruleset: reloading
debug: parent_send_config: configuring pony process
debug: parent_send_config: configuring ca process
debug: init private ssl-tree
debug: smtp: listen on 127.0.0.1 port 25 flags 0x400 pki "" ca ""
debug: smtp: will accept at most 2043 clients
debug: queue: done loading queue into scheduler
debug: smtpd: scanning offline queue...
debug: smtpd: offline scanning done
debug: smtp: new client on listener: 0x22e0e50
0756cab372952195 smtp event=connected address=local host=jrm.no-ip.org
smtp: 0x22a0ec0: fd 16 from queue
smtp: 0x22a0ec0: fd 18 from filter
debug: smtp: 0x22a0ec0: data io done (500 bytes)
filter: deferring eom query...
filter: running eom query...
debug: 0x22a0ec0: end of message, msgflags=0x0000
0756cab372952195 smtp event=message msgid=233ba1ab from=<jrma...@gmail.com> to=<malaqu...@gmail.com> size=500 ndest=1 proto=ESMTP
0756cab372952195 smtp event=message msgid=233ba1ab from=<jrma...@gmail.com> to=<romi...@operamail.com> size=500 ndest=1 proto=ESMTP
debug: scheduler: evp:233ba1ab160e4a66 scheduled (mta)
debug: scheduler: evp:233ba1abcc50d96e scheduled (mta)
0756cab372952195 smtp event=closed reason=quit
debug: smtp: 0x22a0ec0: deleting session: done
debug: mta: received evp:233ba1ab160e4a66 for <malaqu...@gmail.com>
debug: mta: draining [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx] refcount=1, ntask=1, nconnector=0, nconn=0
debug: mta: querying secret for [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx]...
debug: mta: querying MX for [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx]...
debug: mta: [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx] waiting for MX secret
debug: mta: received evp:233ba1abcc50d96e for <romi...@operamail.com>
debug: mta: draining [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx] refcount=3, ntask=1, nconnector=0, nconn=0
debug: mta: [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx] waiting for MX secret
debug: mta: ... got secret for [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx]: AGpybWFsYXEAZ2VlQHdvbyE=
debug: mta: draining [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx] refcount=2, ntask=1, nconnector=0, nconn=0
debug: mta: [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx] waiting for MX
debug: MXs for domain smtp.gmail.com:
	64.233.190.109 preference -1
	64.233.190.108 preference -1
debug: mta: ... got mx (0x22a2c90, smtp.gmail.com, [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx])
debug: mta: draining [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx] refcount=1, ntask=1, nconnector=0, nconn=0
debug: mta: querying source for [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx]...
debug: mta: ... got source for [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx]: []
debug: mta: new [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x10000]
debug: mta: connecting with [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x0]
debug: mta-routing: searching new route for [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x0]...
debug: mta-routing: selecting candidate route [] <-> 64.233.190.109
debug: mta-routing: skipping route [] <-> 64.233.190.108: current one is better
debug: mta: mta_route_unref(): really discarding route [] <-> 64.233.190.108
debug: mta-routing: spawning new connection on [] <-> 64.233.190.109
debug: mta: 0x22a2060: spawned for relay [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx]
debug: mta: connecting with [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x0]
debug: mta: cannot use [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx] before 2s
debug: mta-routing: no route available for [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x0]: must wait a bit
debug: mta: retrying to connect on [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x0] in 2s...
debug: mta: draining [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx] refcount=3, ntask=1, nconnector=1, nconn=1
debug: mta: scheduling relay [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx] in 1s...
0756cabdfbcdf2c6 mta event=connecting address=tls://64.233.190.109:465 host=gsademo28.google.com
0756cabdfbcdf2c6 mta event=connected
debug: mta: ... timeout for [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx]
debug: mta: draining [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx] refcount=2, ntask=1, nconnector=1, nconn=1
debug: mta: querying source for [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx]...
debug: mta: ... got source for [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx]: []
debug: mta: connecting with [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x20000]
debug: mta: cancelling connector timeout
debug: mta: cannot use [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx] before 1s
debug: mta-routing: no route available for [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x0]: must wait a bit
debug: mta: retrying to connect on [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x0] in 1s...
debug: mta: draining [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx] refcount=3, ntask=1, nconnector=1, nconn=1
debug: mta: scheduling relay [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx] in 10s...
debug: mta: ... timeout for [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x20000]
debug: mta: connecting with [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x0]
debug: mta-routing: searching new route for [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x0]...
debug: mta-routing: skipping route [] <-> 64.233.190.109 (gsademo28.google.com): not validated yet
debug: mta-routing: selecting candidate route [] <-> 64.233.190.108
debug: mta-routing: spawning new connection on [] <-> 64.233.190.108
debug: mta: 0x22a39d0: spawned for relay [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx]
debug: mta: connecting with [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x0]
debug: mta: cannot use [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx] before 2s
debug: mta-routing: no route available for [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x0]: must wait a bit
debug: mta: retrying to connect on [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x0] in 2s...
0756cabe792fd85e mta event=connecting address=tls://64.233.190.108:465 host=gsademo27.google.com
0756cabe792fd85e mta event=connected
debug: mta: ... timeout for [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x20000]
debug: mta: connecting with [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x0]
debug: mta-routing: searching new route for [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x0]...
debug: mta-routing: skipping route [] <-> 64.233.190.109 (gsademo28.google.com): not validated yet
debug: mta-routing: skipping route [] <-> 64.233.190.108 (gsademo27.google.com): not validated yet
debug: mta: hit route limit
debug: mta-routing: no route available for [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x0]: limits reached
debug: mta: retrying to connect on [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x0] in 5s...
debug: mta: ... timeout for [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x20000]
debug: mta: connecting with [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x0]
debug: mta-routing: searching new route for [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x0]...
debug: mta-routing: skipping route [] <-> 64.233.190.109 (gsademo28.google.com): not validated yet
debug: mta-routing: skipping route [] <-> 64.233.190.108 (gsademo27.google.com): not validated yet
debug: mta: hit route limit
debug: mta-routing: no route available for [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x0]: limits reached
debug: mta: retrying to connect on [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x0] in 5s...
debug: mta: 0x22a2060: disconnected in state MTA_BANNER
0756cabdfbcdf2c6 mta event=error reason=Connection closed unexpectedly
debug: mta: 0x22a2060: session done
debug: mta_route_collect([] <-> 64.233.190.109 (gsademo28.google.com))
smtp-out: Disabling route [] <-> 64.233.190.109 (gsademo28.google.com) for 15s
debug: mta: connecting with [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x20000]
debug: mta: cancelling connector timeout
debug: mta-routing: searching new route for [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x0]...
debug: mta-routing: skipping route [] <-> 64.233.190.109 (gsademo28.google.com): suspend
debug: mta-routing: skipping route [] <-> 64.233.190.108 (gsademo27.google.com): not validated yet
debug: mta: hit route limit
debug: mta-routing: no route available for [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x0]: limits reached
debug: mta: retrying to connect on [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x0] in 5s...
debug: mta: ... timeout for [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx]
debug: mta: draining [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx] refcount=2, ntask=1, nconnector=1, nconn=1
debug: mta: querying source for [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx]...
debug: mta: ... got source for [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx]: []
debug: mta: connecting with [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x20000]
debug: mta: cancelling connector timeout
debug: mta-routing: searching new route for [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x0]...
debug: mta-routing: skipping route [] <-> 64.233.190.109 (gsademo28.google.com): suspend
debug: mta-routing: skipping route [] <-> 64.233.190.108 (gsademo27.google.com): not validated yet
debug: mta: hit route limit
debug: mta-routing: no route available for [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x0]: limits reached
debug: mta: retrying to connect on [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x0] in 5s...
debug: mta: draining [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx] refcount=3, ntask=1, nconnector=1, nconn=1
debug: mta: scheduling relay [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx] in 10s...
debug: mta: 0x22a39d0: disconnected in state MTA_BANNER
0756cabe792fd85e mta event=error reason=Connection closed unexpectedly
debug: mta: 0x22a39d0: session done
debug: mta_route_collect([] <-> 64.233.190.108 (gsademo27.google.com))
smtp-out: Disabling route [] <-> 64.233.190.108 (gsademo27.google.com) for 15s
debug: mta: connecting with [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x20000]
debug: mta: cancelling connector timeout
debug: mta-routing: searching new route for [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x0]...
debug: mta-routing: skipping route [] <-> 64.233.190.109 (gsademo28.google.com): suspend
debug: mta-routing: skipping route [] <-> 64.233.190.108 (gsademo27.google.com): suspend
smtp-out: No valid route for [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x0]
debug: mta-routing: no route available for [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x8]: errors on connector
debug: mta: ... timeout for [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx]
debug: mta: draining [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx] refcount=1, ntask=1, nconnector=1, nconn=0
debug: mta: querying source for [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx]...
debug: mta: ... got source for [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx]: []
debug: mta: connecting with [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x8]
debug: mta: connector error
debug: mta: draining [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx] refcount=2, ntask=1, nconnector=1, nconn=0
debug: mta: querying source for [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx]...
debug: mta: ... got source for [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx]: []
debug: mta: connecting with [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x8]
debug: mta: connector error
debug: mta: draining [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx] refcount=3, ntask=1, nconnector=1, nconn=0
debug: mta_flush([relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx], 81, "Network error on destination MXs")
0000000000000000 mta event=delivery evpid=233ba1ab160e4a66 from=<jrma...@gmail.com> to=<malaqu...@gmail.com> rcpt=<-> source=- relay=smtp.gmail.com delay=21s result=TempFail stat=Network error on destination MXs
0000000000000000 mta event=delivery evpid=233ba1abcc50d96e from=<jrma...@gmail.com> to=<romi...@operamail.com> rcpt=<-> source=- relay=smtp.gmail.com delay=21s result=TempFail stat=Network error on destination MXs
debug: mta: freeing [relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx]
debug: mta: freeing [connector:[]->[relay:smtp.gmail.com,port=465,starttls,auth=secrets:gmail.jrmalaq,mx],0x8]
debug: mta: flush for 233ba1abcc50d96e (-> romi...@operamail.com)
debug: mta: flush for 233ba1ab160e4a66 (-> malaqu...@gmail.com)
smtp-out: Enabling route [] <-> 64.233.190.109 (gsademo28.google.com)
debug: mta: mta_route_unref(): really discarding route [] <-> 64.233.190.109 (gsademo28.google.com)
smtp-out: Enabling route [] <-> 64.233.190.108 (gsademo27.google.com)
debug: mta: mta_route_unref(): really discarding route [] <-> 64.233.190.108 (gsademo27.google.com)

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