Hello, I am trying to setup stunnel to send email using gmail smtp server trough Oracle Database.

I first tested on my windows machine. I installed and configured stunnel and it worked fine.

But now I tried to do the same on our server (RHEL 6.4) and it doesn't work.

I can successfuly telnet the 25 port:

[root@server1 stunnel]# telnet localhost 25

Trying 127.0.0.1...

Connected to localhost.

Escape character is '^]'.

220 mx.google.com ESMTP so2sm18740691pbc.5 - gsmtp

When I send the email, i receive this error: SMTP permanent error: 534 5.7.14 54 ef10sm21262349pac.1 - gsmtp

anyone have any idea?

the stunnel.conf:

pid = /stunnel.pid

output = /var/log/stunnel.log

compression = zlib

sslVersion = all

options = NO_SSLv2

debug = 7

[gmail-smtp]

client = yes

accept = localhost:25

connect = smtp.gmail.com:465

Here is the Stunnel log:

2013.11.17 15:58:34 LOG7[23729:139952118699968]: gmail-smtp accepted FD=13 from 127.0.0.1:56089

2013.11.17 15:58:34 LOG7[23729:139952118695680]: gmail-smtp started

2013.11.17 15:58:34 LOG7[23729:139952118695680]: FD 13 in non-blocking mode

2013.11.17 15:58:34 LOG7[23729:139952118695680]: Waiting for a libwrap process

2013.11.17 15:58:34 LOG7[23729:139952118695680]: Acquired libwrap process #0

2013.11.17 15:58:34 LOG7[23729:139952118695680]: Releasing libwrap process #0

2013.11.17 15:58:34 LOG7[23729:139952118695680]: Released libwrap process #0

2013.11.17 15:58:34 LOG7[23729:139952118695680]: gmail-smtp permitted by libwrap from 127.0.0.1:56089

2013.11.17 15:58:34 LOG5[23729:139952118695680]: gmail-smtp accepted connection from 127.0.0.1:56089

2013.11.17 15:58:34 LOG7[23729:139952118695680]: FD 14 in non-blocking mode

2013.11.17 15:58:34 LOG6[23729:139952118695680]: connect_blocking: connecting 74.125.129.108:465

2013.11.17 15:58:34 LOG7[23729:139952118695680]: connect_blocking: s_poll_wait 74.125.129.108:465: waiting 10 seconds

2013.11.17 15:58:34 LOG5[23729:139952118695680]: connect_blocking: connected 74.125.129.108:465

2013.11.17 15:58:34 LOG5[23729:139952118695680]: gmail-smtp connected remote server from 172.31.22.161:51067

2013.11.17 15:58:34 LOG7[23729:139952118695680]: Remote FD=14 initialized

2013.11.17 15:58:34 LOG7[23729:139952118695680]: SSL state (connect): before/connect initialization

2013.11.17 15:58:34 LOG7[23729:139952118695680]: SSL state (connect): SSLv2/v3 write client hello A

2013.11.17 15:58:34 LOG7[23729:139952118695680]: SSL state (connect): SSLv3 read server hello A

2013.11.17 15:58:34 LOG7[23729:139952118695680]: SSL state (connect): SSLv3 read server certificate A

2013.11.17 15:58:34 LOG7[23729:139952118695680]: SSL state (connect): SSLv3 read server done A

2013.11.17 15:58:34 LOG7[23729:139952118695680]: SSL state (connect): SSLv3 write client key exchange A

2013.11.17 15:58:34 LOG7[23729:139952118695680]: SSL state (connect): SSLv3 write change cipher spec A

2013.11.17 15:58:34 LOG7[23729:139952118695680]: SSL state (connect): SSLv3 write finished A

2013.11.17 15:58:34 LOG7[23729:139952118695680]: SSL state (connect): SSLv3 flush data

2013.11.17 15:58:34 LOG7[23729:139952118695680]: SSL state (connect): SSLv3 read server session ticket A

2013.11.17 15:58:34 LOG7[23729:139952118695680]: SSL state (connect): SSLv3 read finished A

2013.11.17 15:58:34 LOG7[23729:139952118695680]: 1 items in the session cache

2013.11.17 15:58:34 LOG7[23729:139952118695680]: 1 client connects (SSL_connect())

2013.11.17 15:58:34 LOG7[23729:139952118695680]: 1 client connects that finished

2013.11.17 15:58:34 LOG7[23729:139952118695680]: 0 client renegotiations requested

2013.11.17 15:58:34 LOG7[23729:139952118695680]: 0 server connects (SSL_accept())

2013.11.17 15:58:34 LOG7[23729:139952118695680]: 0 server connects that finished

2013.11.17 15:58:34 LOG7[23729:139952118695680]: 0 server renegotiations requested

2013.11.17 15:58:34 LOG7[23729:139952118695680]: 0 session cache hits

2013.11.17 15:58:34 LOG7[23729:139952118695680]: 0 external session cache hits

2013.11.17 15:58:34 LOG7[23729:139952118695680]: 0 session cache misses

2013.11.17 15:58:34 LOG7[23729:139952118695680]: 0 session cache timeouts

2013.11.17 15:58:34 LOG6[23729:139952118695680]: SSL connected: new session negotiated

2013.11.17 15:58:34 LOG6[23729:139952118695680]: Negotiated ciphers: RC4-SHA SSLv3 Kx=RSA Au=RSA Enc=RC4(128) Mac=SHA1

2013.11.17 15:58:34 LOG7[23729:139952118695680]: SSL socket closed on SSL_read

2013.11.17 15:58:34 LOG7[23729:139952118695680]: Socket write shutdown

2013.11.17 15:58:34 LOG5[23729:139952118695680]: Connection closed: 90 bytes sent to SSL, 860 bytes sent to socket

2013.11.17 15:58:34 LOG7[23729:139952118695680]: gmail-smtp finished (0 left)

2013.11.17 16:01:01 LOG7[23729:139952118699968]: gmail-smtp accepted FD=13 from 127.0.0.1:56120

2013.11.17 16:01:01 LOG7[23729:139952118695680]: gmail-smtp started

2013.11.17 16:01:01 LOG7[23729:139952118695680]: FD 13 in non-blocking mode

2013.11.17 16:01:01 LOG7[23729:139952118695680]: Waiting for a libwrap process

2013.11.17 16:01:01 LOG7[23729:139952118695680]: Acquired libwrap process #0

2013.11.17 16:01:01 LOG7[23729:139952118695680]: Releasing libwrap process #0

2013.11.17 16:01:01 LOG7[23729:139952118695680]: Released libwrap process #0

2013.11.17 16:01:01 LOG7[23729:139952118695680]: gmail-smtp permitted by libwrap from 127.0.0.1:56120

2013.11.17 16:01:01 LOG5[23729:139952118695680]: gmail-smtp accepted connection from 127.0.0.1:56120

2013.11.17 16:01:01 LOG7[23729:139952118695680]: FD 14 in non-blocking mode

2013.11.17 16:01:01 LOG6[23729:139952118695680]: connect_blocking: connecting 74.125.129.109:465

2013.11.17 16:01:01 LOG7[23729:139952118695680]: connect_blocking: s_poll_wait 74.125.129.109:465: waiting 10 seconds

2013.11.17 16:01:01 LOG5[23729:139952118695680]: connect_blocking: connected 74.125.129.109:465

2013.11.17 16:01:01 LOG5[23729:139952118695680]: gmail-smtp connected remote server from 172.31.22.161:56971

2013.11.17 16:01:01 LOG7[23729:139952118695680]: Remote FD=14 initialized

2013.11.17 16:01:01 LOG7[23729:139952118695680]: SSL state (connect): before/connect initialization

2013.11.17 16:01:01 LOG7[23729:139952118695680]: SSL state (connect): SSLv3 write client hello A

2013.11.17 16:01:01 LOG7[23729:139952118695680]: SSL state (connect): SSLv3 read server hello A

2013.11.17 16:01:01 LOG7[23729:139952118695680]: SSL state (connect): SSLv3 read finished A

2013.11.17 16:01:01 LOG7[23729:139952118695680]: SSL state (connect): SSLv3 write change cipher spec A

2013.11.17 16:01:01 LOG7[23729:139952118695680]: SSL state (connect): SSLv3 write finished A

2013.11.17 16:01:01 LOG7[23729:139952118695680]: SSL state (connect): SSLv3 flush data

2013.11.17 16:01:01 LOG7[23729:139952118695680]: 1 items in the session cache

2013.11.17 16:01:01 LOG7[23729:139952118695680]: 2 client connects (SSL_connect())

2013.11.17 16:01:01 LOG7[23729:139952118695680]: 2 client connects that finished

2013.11.17 16:01:01 LOG7[23729:139952118695680]: 0 client renegotiations requested

2013.11.17 16:01:01 LOG7[23729:139952118695680]: 0 server connects (SSL_accept())

2013.11.17 16:01:01 LOG7[23729:139952118695680]: 0 server connects that finished

2013.11.17 16:01:01 LOG7[23729:139952118695680]: 0 server renegotiations requested

2013.11.17 16:01:01 LOG7[23729:139952118695680]: 1 session cache hits

2013.11.17 16:01:01 LOG7[23729:139952118695680]: 0 external session cache hits

2013.11.17 16:01:01 LOG7[23729:139952118695680]: 0 session cache misses

2013.11.17 16:01:01 LOG7[23729:139952118695680]: 0 session cache timeouts

2013.11.17 16:01:01 LOG6[23729:139952118695680]: SSL connected: previous session reused

2013.11.17 16:01:02 LOG7[23729:139952118695680]: SSL socket closed on SSL_read

2013.11.17 16:01:02 LOG7[23729:139952118695680]: Socket write shutdown

2013.11.17 16:01:02 LOG5[23729:139952118695680]: Connection closed: 241 bytes sent to SSL, 825 bytes sent to socket

2013.11.17 16:01:02 LOG7[23729:139952118695680]: gmail-smtp finished (0 left)

Thanks a lot