[stunnel-users] unable to send SMTP over SSL

[Paul Hargrove]

Hi,

I'm a new user using stunnel-5.03 on Windows SBS 2003.

I can't send email from Exchange but can from Outlook with same credentials
on same network.

Email gets stuck in the exchange smtp queue.

Simple config:

; * Global options

debug = 7
output = stunnel.log
engine = capi
options = NO_SSLv2

; * Service definition

[SMTP]
client = yes
accept = 8465
connect = smtp.virginmedia.com:465
protocol = smtp


Logs look good but nothing seems to go:

2014.08.08 22:15:07 LOG7[7284]: Dispatching signals from the signal pipe
2014.08.08 22:15:07 LOG7[7284]: Processing SIGNAL_RELOAD_CONFIG
2014.08.08 22:15:07 LOG5[7284]: Reading configuration from file stunnel.conf
2014.08.08 22:15:07 LOG7[7284]: Enabling support for engine 'capi'
2014.08.08 22:15:07 LOG7[7284]: Initializing engine #1 (capi)
2014.08.08 22:15:07 LOG6[7284]: Engine #1 (capi) initialized
2014.08.08 22:15:07 LOG5[7284]: FIPS mode disabled
2014.08.08 22:15:07 LOG7[7284]: Compression disabled
2014.08.08 22:15:07 LOG7[7284]: Snagged 64 random bytes from C:/.rnd
2014.08.08 22:15:07 LOG7[7284]: Wrote 1024 new random bytes to C:/.rnd
2014.08.08 22:15:07 LOG7[7284]: PRNG seeded successfully
2014.08.08 22:15:07 LOG6[7284]: Initializing service [SMTP]
2014.08.08 22:15:08 LOG7[7284]: No private key specified
2014.08.08 22:15:08 LOG7[7284]: SSL options set: 0x01000004
2014.08.08 22:15:08 LOG5[7284]: Configuration successful
2014.08.08 22:15:08 LOG7[7284]: Closing service [SMTP]
2014.08.08 22:15:08 LOG7[7284]: Service [SMTP] closed (FD=292)
2014.08.08 22:15:08 LOG7[7284]: Sessions cached before flush: 7
2014.08.08 22:15:08 LOG7[7284]: Sessions cached after flush: 0
2014.08.08 22:15:08 LOG7[7284]: Service [SMTP] closed
2014.08.08 22:15:08 LOG7[7284]: Service [SMTP] (FD=292) bound to
0.0.0.0:8465
2014.08.08 22:15:08 LOG7[7284]: Signal pipe is empty
2014.08.08 22:16:03 LOG7[7284]: Service [SMTP] accepted (FD=392) from
127.0.0.1:26642
2014.08.08 22:16:03 LOG7[7284]: Creating a new thread
2014.08.08 22:16:03 LOG7[7284]: New thread created
2014.08.08 22:16:03 LOG7[7184]: Service [SMTP] started
2014.08.08 22:16:03 LOG5[7184]: Service [SMTP] accepted connection from
127.0.0.1:26642
2014.08.08 22:16:03 LOG6[7184]: s_connect: connecting 62.254.26.219:465
2014.08.08 22:16:03 LOG7[7184]: s_connect: s_poll_wait 62.254.26.219:465:
waiting 10 seconds
2014.08.08 22:16:03 LOG5[7184]: s_connect: connected 62.254.26.219:465
2014.08.08 22:16:03 LOG5[7184]: Service [SMTP] connected remote server from
10.0.0.2:26643
2014.08.08 22:16:03 LOG7[7184]: Remote socket (FD=688) initialized
2014.08.08 22:16:14 LOG3[7184]: fd_getline: Unexpected socket close
2014.08.08 22:16:14 LOG5[7184]: Connection reset: 0 byte(s) sent to SSL, 0
byte(s) sent to socket
2014.08.08 22:16:14 LOG7[7184]: Remote socket (FD=688) closed
2014.08.08 22:16:14 LOG7[7184]: Local socket (FD=392) closed
2014.08.08 22:16:14 LOG7[7184]: Service [SMTP] finished (0 left)
2014.08.08 22:16:14 LOG7[7184]: str_stats: 3 block(s), 4294966138 data
byte(s), 150 control byte(s)
2014.08.08 22:16:14 LOG7[7184]: str_stats: 20 byte(s) at
..\src\network.c:413
2014.08.08 22:16:14 LOG7[7184]: str_stats: 20 byte(s) at
..\src\network.c:412
2014.08.08 22:16:14 LOG7[7184]: str_stats: 20 byte(s) at
..\src\network.c:411


If I rem out the protocol = smtp then the mails go from the queue and  the
logs seem to indicate a success:

2014.08.08 22:02:14 LOG7[7284]: Service [SMTP] accepted (FD=688) from
127.0.0.1:54520
2014.08.08 22:02:14 LOG7[7284]: Creating a new thread
2014.08.08 22:02:14 LOG7[7284]: New thread created
2014.08.08 22:02:14 LOG7[10072]: Service [SMTP] started
2014.08.08 22:02:14 LOG5[10072]: Service [SMTP] accepted connection from
127.0.0.1:54520
2014.08.08 22:02:14 LOG6[10072]: s_connect: connecting 62.254.26.219:465
2014.08.08 22:02:14 LOG7[10072]: s_connect: s_poll_wait 62.254.26.219:465:
waiting 10 seconds
2014.08.08 22:02:14 LOG5[10072]: s_connect: connected 62.254.26.219:465
2014.08.08 22:02:14 LOG5[10072]: Service [SMTP] connected remote server
from 10.0.0.2:54521
2014.08.08 22:02:14 LOG7[10072]: Remote socket (FD=456) initialized
2014.08.08 22:02:14 LOG6[10072]: SNI: sending servername:
smtp.virginmedia.com
2014.08.08 22:02:14 LOG7[10072]: SSL state (connect): before/connect
initialization
2014.08.08 22:02:14 LOG7[10072]: SSL state (connect): SSLv3 write client
hello A
2014.08.08 22:02:14 LOG7[10072]: SSL state (connect): SSLv3 read server
hello A
2014.08.08 22:02:14 LOG7[10072]: SSL state (connect): SSLv3 read finished A
2014.08.08 22:02:14 LOG7[10072]: SSL state (connect): SSLv3 write change
cipher spec A
2014.08.08 22:02:14 LOG7[10072]: SSL state (connect): SSLv3 write finished A
2014.08.08 22:02:14 LOG7[10072]: SSL state (connect): SSLv3 flush data
2014.08.08 22:02:14 LOG7[10072]:    6 items in the session cache
2014.08.08 22:02:14 LOG7[10072]:   13 client connects (SSL_connect())
2014.08.08 22:02:14 LOG7[10072]:   13 client connects that finished
2014.08.08 22:02:14 LOG7[10072]:    0 client renegotiations requested
2014.08.08 22:02:14 LOG7[10072]:    0 server connects (SSL_accept())
2014.08.08 22:02:14 LOG7[10072]:    0 server connects that finished
2014.08.08 22:02:14 LOG7[10072]:    0 server renegotiations requested
2014.08.08 22:02:14 LOG7[10072]:    7 session cache hits
2014.08.08 22:02:14 LOG7[10072]:    0 external session cache hits
2014.08.08 22:02:14 LOG7[10072]:    0 session cache misses
2014.08.08 22:02:14 LOG7[10072]:    0 session cache timeouts
2014.08.08 22:02:14 LOG6[10072]: SSL connected: previous session reused
2014.08.08 22:02:16 LOG6[10072]: Read socket closed (readsocket)
2014.08.08 22:02:16 LOG7[10072]: Sending close_notify alert
2014.08.08 22:02:16 LOG7[10072]: SSL alert (write): warning: close notify
2014.08.08 22:02:16 LOG6[10072]: SSL_shutdown successfully sent
close_notify alert
2014.08.08 22:02:16 LOG6[10072]: SSL socket closed (SSL_read)
2014.08.08 22:02:16 LOG7[10072]: Sent socket write shutdown
2014.08.08 22:02:16 LOG5[10072]: Connection closed: 80 byte(s) sent to SSL,
298 byte(s) sent to socket
2014.08.08 22:02:16 LOG7[10072]: Remote socket (FD=456) closed
2014.08.08 22:02:16 LOG7[10072]: Local socket (FD=688) closed
2014.08.08 22:02:16 LOG7[10072]: Service [SMTP] finished (0 left)
2014.08.08 22:02:16 LOG7[10072]: str_stats: 3 block(s), 4294963672 data
byte(s), 150 control byte(s)
2014.08.08 22:02:16 LOG7[10072]: str_stats: 20 byte(s) at
..\src\network.c:413
2014.08.08 22:02:16 LOG7[10072]: str_stats: 20 byte(s) at
..\src\network.c:412
2014.08.08 22:02:16 LOG7[10072]: str_stats: 20 byte(s) at
..\src\network.c:411

but all Mails bounce with:

There was a SMTP communication problem with the recipient's email server.
 Please contact your system administrator.
  <server.domain.local #5.5.0 smtp;530 Authentication Required (VM401)>

Any ideas?
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