<html><head><meta http-equiv="Content-Type" content="text/html charset=utf-8"></head><body style="word-wrap: break-word; -webkit-nbsp-mode: space; -webkit-line-break: after-white-space;" class="">I am running Stunnel 5.14 on my Mac mail server (OS X 10.7.5), but trying to send emails using ports 465 & 587 does not work:<div class=""><br class=""></div><div class="">Mail.app says:</div><div class=""><br class=""></div><div class=""><div style="margin: 0px; font-size: 11px; font-family: 'Helvetica Neue';" class="">Mail was unable to connect to server “<a href="http://mail.bordo.com.au" class="">mail.bordo.com.au</a>” using SSL on port 587. Verify that this server supports SSL and that your account settings are correct.</div></div><div style="margin: 0px; font-size: 11px; font-family: 'Helvetica Neue';" class=""><br class=""></div><div style="margin: 0px; font-size: 11px; font-family: 'Helvetica Neue';" class=""><span style="font-family: Helvetica; font-size: 12px;" class="">Log from Stunnel is:</span></div><div style="margin: 0px; font-size: 11px; font-family: 'Helvetica Neue';" class=""><span style="font-family: Helvetica; font-size: 12px;" class=""><br class=""></span></div><div style="margin: 0px;" class=""><div style="margin: 0px;" class="">2015.03.31 09:27:56 LOG7[ui]: Clients allowed=500</div><div style="margin: 0px;" class="">2015.03.31 09:27:56 LOG5[ui]: stunnel 5.14 on x86_64-apple-darwin11.4.2 platform</div><div style="margin: 0px;" class="">2015.03.31 09:27:56 LOG5[ui]: Compiled/running with OpenSSL 1.0.2a 19 Mar 2015</div><div style="margin: 0px;" class="">2015.03.31 09:27:56 LOG5[ui]: Threading:PTHREAD Sockets:SELECT,IPv6 TLS:ENGINE,FIPS,OCSP,PSK,SNI Auth:LIBWRAP</div><div style="margin: 0px;" class="">2015.03.31 09:27:56 LOG7[ui]: errno: (*__error())</div><div style="margin: 0px;" class="">2015.03.31 09:27:56 LOG5[ui]: Reading configuration from file /usr/local/etc/stunnel/stunnel.conf</div><div style="margin: 0px;" class="">2015.03.31 09:27:56 LOG5[ui]: UTF-8 byte order mark not detected</div><div style="margin: 0px;" class="">2015.03.31 09:27:56 LOG5[ui]: FIPS mode disabled</div><div style="margin: 0px;" class="">2015.03.31 09:27:56 LOG7[ui]: Compression disabled</div><div style="margin: 0px;" class="">2015.03.31 09:27:56 LOG7[ui]: Snagged 64 random bytes from /dev/urandom</div><div style="margin: 0px;" class="">2015.03.31 09:27:56 LOG7[ui]: PRNG seeded successfully</div><div style="margin: 0px;" class="">2015.03.31 09:27:56 LOG6[ui]: Initializing service [ssmtp]</div><div style="margin: 0px;" class="">2015.03.31 09:27:56 LOG6[ui]: Loading certificate from file: /usr/local/etc/postfix/smtpd.cert</div><div style="margin: 0px;" class="">2015.03.31 09:27:56 LOG6[ui]: Loading key from file: /usr/local/etc/postfix/smtpd.key</div><div style="margin: 0px;" class="">2015.03.31 09:27:56 LOG7[ui]: Private key check succeeded</div><div style="margin: 0px;" class="">2015.03.31 09:27:56 LOG7[ui]: DH initialization</div><div style="margin: 0px;" class="">2015.03.31 09:27:56 LOG7[ui]: Using DH parameters from /usr/local/etc/postfix/smtpd.cert</div><div style="margin: 0px;" class="">2015.03.31 09:27:56 LOG7[ui]: DH initialized with 2048-bit key</div><div style="margin: 0px;" class="">2015.03.31 09:27:56 LOG7[ui]: ECDH initialization</div><div style="margin: 0px;" class="">2015.03.31 09:27:56 LOG7[ui]: ECDH initialized with curve prime256v1</div><div style="margin: 0px;" class="">2015.03.31 09:27:56 LOG7[ui]: SSL options: 0x03000004 (+0x03000000, -0x00000000)</div><div style="margin: 0px;" class="">2015.03.31 09:27:56 LOG6[ui]: Initializing service [ssmtp2]</div><div style="margin: 0px;" class="">2015.03.31 09:27:56 LOG6[ui]: Loading certificate from file: /usr/local/etc/postfix/smtpd.cert</div><div style="margin: 0px;" class="">2015.03.31 09:27:56 LOG6[ui]: Loading key from file: /usr/local/etc/postfix/smtpd.key</div><div style="margin: 0px;" class="">2015.03.31 09:27:56 LOG7[ui]: Private key check succeeded</div><div style="margin: 0px;" class="">2015.03.31 09:27:56 LOG7[ui]: DH initialization</div><div style="margin: 0px;" class="">2015.03.31 09:27:56 LOG7[ui]: Using DH parameters from /usr/local/etc/postfix/smtpd.cert</div><div style="margin: 0px;" class="">2015.03.31 09:27:56 LOG7[ui]: DH initialized with 2048-bit key</div><div style="margin: 0px;" class="">2015.03.31 09:27:56 LOG7[ui]: ECDH initialization</div><div style="margin: 0px;" class="">2015.03.31 09:27:56 LOG7[ui]: ECDH initialized with curve prime256v1</div><div style="margin: 0px;" class="">2015.03.31 09:27:56 LOG7[ui]: SSL options: 0x03000004 (+0x03000000, -0x00000000)</div><div style="margin: 0px;" class="">2015.03.31 09:27:56 LOG5[ui]: Configuration successful</div><div style="margin: 0px;" class="">2015.03.31 09:27:56 LOG7[ui]: Listening file descriptor created (FD=6)</div><div style="margin: 0px;" class="">2015.03.31 09:27:56 LOG7[ui]: Service [ssmtp] (FD=6) bound to 0.0.0.0:465</div><div style="margin: 0px;" class="">2015.03.31 09:27:56 LOG7[ui]: Listening file descriptor created (FD=7)</div><div style="margin: 0px;" class="">2015.03.31 09:27:56 LOG7[ui]: Service [ssmtp2] (FD=7) bound to 0.0.0.0:587</div><div style="margin: 0px;" class=""><br class=""></div><div style="margin: 0px;" class=""><br class=""></div><div style="margin: 0px;" class="">/usr/local/etc/stunnel/stunnel.conf has:</div><div style="margin: 0px;" class=""><br class=""></div><div style="margin: 0px;" class=""><div style="margin: 0px;" class="">[ssmtp]</div><div style="margin: 0px;" class="">client = no</div><div style="margin: 0px;" class="">accept = 465</div><div style="margin: 0px;" class="">connect = 127.0.0.1:25</div><div style="margin: 0px;" class=""><br class=""></div><div style="margin: 0px;" class="">[ssmtp2]</div><div style="margin: 0px;" class="">client = no</div><div style="margin: 0px;" class="">accept = 587</div><div style="margin: 0px;" class="">connect = 127.0.0.1:25</div><div style="margin: 0px;" class=""><br class=""></div><div style="margin: 0px;" class="">The mail server is running on the same machine.</div><div style="margin: 0px;" class=""><br class=""></div><div style="margin: 0px;" class="">I can send emails using port 25 with no SSL. (I have to have the ‘Allow insecure authentication’ ticked).</div><div style="margin: 0px;" class=""><br class=""></div><div style="margin: 0px;" class="">When I try to send using ports 587 or 465 there is nothing logged by stunnel (or anywhere else that I can see).</div><div style="margin: 0px;" class=""><br class=""></div><div style="margin: 0px;" class="">Firewall is not blocking anything:</div><div style="margin: 0px;" class=""><br class=""></div><div style="margin: 0px;" class=""><div style="margin: 0px;" class="">sudo ipfw list</div><div style="margin: 0px;" class="">65535 allow ip from any to any</div></div><div style="margin: 0px;" class=""><br class=""></div><div style="margin: 0px;" class="">Postfix is the SMTP server, Dovecot for IMAP.</div><div style="margin: 0px;" class=""><br class=""></div><div style="margin: 0px;" class="">Any suggestions?</div><div style="margin: 0px;" class=""><br class=""></div><div style="margin: 0px;" class="">Thanks,</div><div style="margin: 0px;" class=""><br class=""></div><div style="margin: 0px;" class="">James.</div></div></div></body></html>