My observations:
Success, Somewhat .

Followed instructions in the Link from eric, http://wiki2.dovecot.org/SSL
created certs etc etc., disabled plaintext auth

Setting up outlook 2007 with " new " account, it tries to auto detect server settings
At same time I am logged into server , and run
tail -f /var/log/dovect.log ( just to see progress)

tail -f /var/log/dovecot.log
May 01 08:54:49 auth-worker: Error: Attempting to rebuild connection to SQL server May 01 08:54:49 auth-worker: Error: vmysql: connection rebuild failed: Table 'vpopmail.users' doesn't exist May 01 08:54:49 auth-worker: Error: vmysql: sql error[3]: Table 'vpopmail.users' doesn't exist May 01 08:54:49 auth-worker: Error: Attempting to rebuild connection to SQL server May 01 08:54:49 auth-worker: Error: vmysql: connection rebuild failed: Table 'vpopmail.users' doesn't exist

**Missing Table  concerned me ** Is there a mysql problem here?

Mean while, Outlook fails initial connect with encrypted connection, so it moves on, I accept cert, etc, outlook finishes setup.
( IP address`s and host name changed to protect the innocent : ) )
May 01 08:54:51 pop3-login: Info: Disconnected (tried to use disallowed plaintext auth): user=<admin>, method=DIGEST-MD5, rip=1.2.3.4, lip=5.5.5.5, session=<9xq/2Ff4GwBC9Ol1> May 01 08:54:55 imap-login: Info: Login: user=<[email protected]>, method=DIGEST-MD5, rip=1.2.3.4, lip=5.6.7.8, mpid=2258, session=<8yC/2Ff4HQBC9Ol1> May 01 08:54:55 imap([email protected]): Info: Disconnected: Logged out in=11 out=408 May 01 08:54:55 pop3-login: Info: Login: user=<[email protected]>, method=DIGEST-MD5, rip=1.2.3.4, lip=5.6.7.8, mpid=2259, session=<lhPe2Ff4HwBC9Ol1> May 01 08:54:55 pop3([email protected]): Info: Disconnected: Logged out top=0/0, retr=0/0, del=0/4, size=9372 May 01 08:55:00 imap-login: Info: Login: user=<[email protected]>, method=DIGEST-MD5, rip=1.2.3.4, lip=5.6.7.8, mpid=2269, session=<sRh02Vf4JABC9Ol1> May 01 08:55:00 imap([email protected]): Info: Disconnected: Disconnected in IDLE in=11 out=372

Checked outlook, and changed advanced settings from port 143 to 993, and port 25 to 587

May 01 08:55:50 imap-login: Info: Login: user=<[email protected]>, method=DIGEST-MD5, rip=1.2.3.4, lip=5.6.7.8, mpid=2309, TLS, session=<m8Jh3Ff4LgBC9Ol1> May 01 08:55:50 imap([email protected]): Info: Disconnected: Disconnected in IDLE in=11 out=372 May 01 08:55:57 imap-login: Info: Login: user=<[email protected]>, method=DIGEST-MD5, rip=1.2.3.4, lip=5.6.7.8, mpid=2326, TLS, session=<P0bP3Ff4NABC9Ol1> May 01 08:55:57 imap-login: Info: Login: user=<[email protected]>, method=DIGEST-MD5, rip=1.2.3.4, lip=5.6.7.8, mpid=2327, TLS, session=<AGnP3Ff4NQBC9Ol1> May 01 08:55:57 imap-login: Info: Login: user=<[email protected]>, method=DIGEST-MD5, rip=1.2.3.4, lip=5.6.7.8, mpid=2329, TLS, session=<zZLU3Ff4NgBC9Ol1> May 01 08:55:57 imap-login: Info: Login: user=<[email protected]>, method=DIGEST-MD5, rip=1.2.3.4, lip=5.6.7.8, mpid=2331, TLS, session=<OWXY3Ff4NwBC9Ol1>

** Outlook is working** This is a live server


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