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 25Trying 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.pidoutput = /var/log/stunnel.logcompression = zlibsslVersion = alloptions = NO_SSLv2debug = 7 [gmail-smtp]client = yesaccept = localhost:25connect = smtp.gmail.com:465

Here is the Stunnel log:2013.11.17 15:58:34 LOG7[23729:139952118699968]: gmail-smtp accepted FD=13 from 127.0.0.1:560892013.11.17 15:58:34 LOG7[23729:139952118695680]: gmail-smtp started2013.11.17 15:58:34 LOG7[23729:139952118695680]: FD 13 in non-blocking mode2013.11.17 15:58:34 LOG7[23729:139952118695680]: Waiting for a libwrap process2013.11.17 15:58:34 LOG7[23729:139952118695680]: Acquired libwrap process #02013.11.17 15:58:34 LOG7[23729:139952118695680]: Releasing libwrap process #02013.11.17 15:58:34 LOG7[23729:139952118695680]: Released libwrap process #02013.11.17 15:58:34 LOG7[23729:139952118695680]: gmail-smtp permitted by libwrap from 127.0.0.1:560892013.11.17 15:58:34 LOG5[23729:139952118695680]: gmail-smtp accepted connection from 127.0.0.1:560892013.11.17 15:58:34 LOG7[23729:139952118695680]: FD 14 in non-blocking mode2013.11.17 15:58:34 LOG6[23729:139952118695680]: connect_blocking: connecting 74.125.129.108:4652013.11.17 15:58:34 LOG7[23729:139952118695680]: connect_blocking: s_poll_wait 74.125.129.108:465: waiting 10 seconds2013.11.17 15:58:34 LOG5[23729:139952118695680]: connect_blocking: connected 74.125.129.108:4652013.11.17 15:58:34 LOG5[23729:139952118695680]: gmail-smtp connected remote server from 172.31.22.161:510672013.11.17 15:58:34 LOG7[23729:139952118695680]: Remote FD=14 initialized2013.11.17 15:58:34 LOG7[23729:139952118695680]: SSL state (connect): before/connect initialization2013.11.17 15:58:34 LOG7[23729:139952118695680]: SSL state (connect): SSLv2/v3 write client hello A2013.11.17 15:58:34 LOG7[23729:139952118695680]: SSL state (connect): SSLv3 read server hello A2013.11.17 15:58:34 LOG7[23729:139952118695680]: SSL state (connect): SSLv3 read server certificate A2013.11.17 15:58:34 LOG7[23729:139952118695680]: SSL state (connect): SSLv3 read server done A2013.11.17 15:58:34 LOG7[23729:139952118695680]: SSL state (connect): SSLv3 write client key exchange A2013.11.17 15:58:34 LOG7[23729:139952118695680]: SSL state (connect): SSLv3 write change cipher spec A2013.11.17 15:58:34 LOG7[23729:139952118695680]: SSL state (connect): SSLv3 write finished A2013.11.17 15:58:34 LOG7[23729:139952118695680]: SSL state (connect): SSLv3 flush data2013.11.17 15:58:34 LOG7[23729:139952118695680]: SSL state (connect): SSLv3 read server session ticket A2013.11.17 15:58:34 LOG7[23729:139952118695680]: SSL state (connect): SSLv3 read finished A2013.11.17 15:58:34 LOG7[23729:139952118695680]: 1 items in the session cache2013.11.17 15:58:34 LOG7[23729:139952118695680]: 1 client connects (SSL_connect())2013.11.17 15:58:34 LOG7[23729:139952118695680]: 1 client connects that finished2013.11.17 15:58:34 LOG7[23729:139952118695680]: 0 client renegotiations requested2013.11.17 15:58:34 LOG7[23729:139952118695680]: 0 server connects (SSL_accept())2013.11.17 15:58:34 LOG7[23729:139952118695680]: 0 server connects that finished2013.11.17 15:58:34 LOG7[23729:139952118695680]: 0 server renegotiations requested2013.11.17 15:58:34 LOG7[23729:139952118695680]: 0 session cache hits2013.11.17 15:58:34 LOG7[23729:139952118695680]: 0 external session cache hits2013.11.17 15:58:34 LOG7[23729:139952118695680]: 0 session cache misses2013.11.17 15:58:34 LOG7[23729:139952118695680]: 0 session cache timeouts2013.11.17 15:58:34 LOG6[23729:139952118695680]: SSL connected: new session negotiated2013.11.17 15:58:34 LOG6[23729:139952118695680]: Negotiated ciphers: RC4-SHA SSLv3 Kx=RSA Au=RSA Enc=RC4(128) Mac=SHA12013.11.17 15:58:34 LOG7[23729:139952118695680]: SSL socket closed on SSL_read2013.11.17 15:58:34 LOG7[23729:139952118695680]: Socket write shutdown2013.11.17 15:58:34 LOG5[23729:139952118695680]: Connection closed: 90 bytes sent to SSL, 860 bytes sent to socket2013.11.17 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 127.0.0.1:561202013.11.17 16:01:01 LOG7[23729:139952118695680]: gmail-smtp started2013.11.17 16:01:01 LOG7[23729:139952118695680]: FD 13 in non-blocking mode2013.11.17 16:01:01 LOG7[23729:139952118695680]: Waiting for a libwrap process2013.11.17 16:01:01 LOG7[23729:139952118695680]: Acquired libwrap process #02013.11.17 16:01:01 LOG7[23729:139952118695680]: Releasing libwrap process #02013.11.17 16:01:01 LOG7[23729:139952118695680]: Released libwrap process #02013.11.17 16:01:01 LOG7[23729:139952118695680]: gmail-smtp permitted by libwrap from 127.0.0.1:561202013.11.17 16:01:01 LOG5[23729:139952118695680]: gmail-smtp accepted connection from 127.0.0.1:561202013.11.17 16:01:01 LOG7[23729:139952118695680]: FD 14 in non-blocking mode2013.11.17 16:01:01 LOG6[23729:139952118695680]: connect_blocking: connecting 74.125.129.109:4652013.11.17 16:01:01 LOG7[23729:139952118695680]: connect_blocking: s_poll_wait 74.125.129.109:465: waiting 10 seconds2013.11.17 16:01:01 LOG5[23729:139952118695680]: connect_blocking: connected 74.125.129.109:4652013.11.17 16:01:01 LOG5[23729:139952118695680]: gmail-smtp connected remote server from 172.31.22.161:569712013.11.17 16:01:01 LOG7[23729:139952118695680]: Remote FD=14 initialized2013.11.17 16:01:01 LOG7[23729:139952118695680]: SSL state (connect): before/connect initialization2013.11.17 16:01:01 LOG7[23729:139952118695680]: SSL state (connect): SSLv3 write client hello A2013.11.17 16:01:01 LOG7[23729:139952118695680]: SSL state (connect): SSLv3 read server hello A2013.11.17 16:01:01 LOG7[23729:139952118695680]: SSL state (connect): SSLv3 read finished A2013.11.17 16:01:01 LOG7[23729:139952118695680]: SSL state (connect): SSLv3 write change cipher spec A2013.11.17 16:01:01 LOG7[23729:139952118695680]: SSL state (connect): SSLv3 write finished A2013.11.17 16:01:01 LOG7[23729:139952118695680]: SSL state (connect): SSLv3 flush data2013.11.17 16:01:01 LOG7[23729:139952118695680]: 1 items in the session cache2013.11.17 16:01:01 LOG7[23729:139952118695680]: 2 client connects (SSL_connect())2013.11.17 16:01:01 LOG7[23729:139952118695680]: 2 client connects that finished2013.11.17 16:01:01 LOG7[23729:139952118695680]: 0 client renegotiations requested2013.11.17 16:01:01 LOG7[23729:139952118695680]: 0 server connects (SSL_accept())2013.11.17 16:01:01 LOG7[23729:139952118695680]: 0 server connects that finished2013.11.17 16:01:01 LOG7[23729:139952118695680]: 0 server renegotiations requested2013.11.17 16:01:01 LOG7[23729:139952118695680]: 1 session cache hits2013.11.17 16:01:01 LOG7[23729:139952118695680]: 0 external session cache hits2013.11.17 16:01:01 LOG7[23729:139952118695680]: 0 session cache misses2013.11.17 16:01:01 LOG7[23729:139952118695680]: 0 session cache timeouts2013.11.17 16:01:01 LOG6[23729:139952118695680]: SSL connected: previous session reused2013.11.17 16:01:02 LOG7[23729:139952118695680]: SSL socket closed on SSL_read2013.11.17 16:01:02 LOG7[23729:139952118695680]: Socket write shutdown2013.11.17 16:01:02 LOG5[23729:139952118695680]: Connection closed: 241 bytes sent to SSL, 825 bytes sent to socket2013.11.17 16:01:02 LOG7[23729:139952118695680]: gmail-smtp finished (0 left)

Thanks a lot