Sorry for hijacking an old thread. But did you solve it somehow?
I have completely new installation of iRedMail 0.9.0 on FreeBSD 10.1.
I am facing similar problems:
If I send mail from Roundcube I got error:
SMTP Error (220): Authentication failed.
In maillog is this:
Jan 3 23:49:01 smtpnew postfix/smtpd[14856]: connect from unknown[xx.xx.xx.xx]
Jan 3 23:49:01 smtpnew postfix/smtpd[14856]: SSL_accept error from unknown[xx.xx.xx.xx]: 0
Jan 3 23:49:01 smtpnew postfix/smtpd[14856]: warning: TLS library problem: error:14094418:SSL routines:SSL3_READ_BYTES:tlsv1 alert unknown ca:/usr/src/secure/lib/libssl/../../../crypto/openssl/ssl/s3_pkt.c:1125:SSL alert number 48:
Jan 3 23:49:01 smtpnew postfix/smtpd[14856]: lost connection after STARTTLS from unknown[xx.xx.xx.xx]
Jan 3 23:49:01 smtpnew roundcube: PHP Deprecated: Non-static method PEAR::raiseError() should not be called statically, assuming $this from incompatible context in /usr/local/www/roundcube/program/lib/Net/SMTP.php on line 611
Jan 3 23:49:01 smtpnew postfix/smtpd[14856]: disconnect from unknown[xx.xx.xx.xx]
Jan 3 23:49:01 smtpnew roundcube: STARTTLS failed ():
Jan 3 23:49:01 smtpnew roundcube: PHP Deprecated: Non-static method PEAR::raiseError() should not be called statically, assuming $this from incompatible context in /usr/local/www/roundcube/program/lib/Net/SMTP.php on line 371
Jan 3 23:49:01 smtpnew roundcube: PHP Deprecated: Non-static method PEAR::raiseError() should not be called statically, assuming $this from incompatible context in /usr/local/www/roundcube/program/lib/Net/SMTP.php on line 265
Jan 3 23:49:01 smtpnew roundcube: SMTP Error: SMTP error: Authentication failure: STARTTLS failed (Code: ) in /usr/local/www/roundcube/program/lib/Roundcube/rcube.php on line 1505 (POST /mail/?_task=mail&_unlock=loading1420325349248&_lang=en_US&_framed=1?_task=mail&_action=send)
