Debian Etch + Postfix + Dovecot + SASL with TLS. Can send mail within lan (at least I did a hour ago before I made changes ) Need help troubleshooting this please. I'm trying to use Postfix to relay thru Earthlinks (my ISP) SMTP server. I'm not sure what to post so I'll start with /var/log/mail.log. can someone please provide some guidance?

Mar 22 12:54:27 docean postfix/smtpd[4906]: connect from unknown[192.168.1.2]
Mar 22 12:54:27 docean postfix/smtpd[4906]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:54:27 docean postfix/smtpd[4906]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:54:27 docean postfix/smtpd[4906]: warning: unknown[192.168.1.2]: SASL LOGIN authentication failed: authentication failure
Mar 22 12:54:27 docean postfix/smtpd[4906]: lost connection after AUTH from unknown[192.168.1.2]
Mar 22 12:54:27 docean postfix/smtpd[4906]: disconnect from unknown[192.168.1.2]
Mar 22 12:54:28 docean postfix/smtpd[4906]: connect from unknown[192.168.1.2]
Mar 22 12:54:28 docean postfix/smtpd[4906]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:54:28 docean postfix/smtpd[4906]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:54:28 docean postfix/smtpd[4906]: warning: unknown[192.168.1.2]: SASL LOGIN authentication failed: authentication failure
Mar 22 12:54:28 docean postfix/smtpd[4906]: lost connection after AUTH from unknown[192.168.1.2]
Mar 22 12:54:28 docean postfix/smtpd[4906]: disconnect from unknown[192.168.1.2]
Mar 22 12:54:29 docean postfix/smtpd[4906]: connect from unknown[192.168.1.2]
Mar 22 12:54:29 docean postfix/smtpd[4906]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:54:29 docean postfix/smtpd[4906]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:54:29 docean postfix/smtpd[4906]: warning: unknown[192.168.1.2]: SASL LOGIN authentication failed: authentication failure
Mar 22 12:54:29 docean postfix/smtpd[4906]: lost connection after AUTH from unknown[192.168.1.2]
Mar 22 12:54:29 docean postfix/smtpd[4906]: disconnect from unknown[192.168.1.2]
Mar 22 12:54:29 docean postfix/smtpd[4906]: connect from unknown[192.168.1.2]
Mar 22 12:54:29 docean postfix/smtpd[4906]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:54:29 docean postfix/smtpd[4906]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:54:29 docean postfix/smtpd[4906]: warning: unknown[192.168.1.2]: SASL LOGIN authentication failed: authentication failure
Mar 22 12:54:29 docean postfix/smtpd[4906]: lost connection after AUTH from unknown[192.168.1.2]
Mar 22 12:54:29 docean postfix/smtpd[4906]: disconnect from unknown[192.168.1.2]
Mar 22 12:55:45 docean postfix/master[4883]: terminating on signal 15
Mar 22 12:55:46 docean postfix/master[4993]: daemon started -- version 2.3.8, configuration /etc/postfix
Mar 22 12:55:53 docean dovecot: pop3-login: Login: user=<danny>, method=PLAIN, rip=192.168.1.2, lip=192.168.1.3
Mar 22 12:55:53 docean dovecot: POP3(danny): Disconnected: Logged out top=0/0, retr=0/0, del=0/0, size=0
Mar 22 12:55:54 docean postfix/smtpd[5002]: connect from unknown[192.168.1.2]
Mar 22 12:55:54 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:55:54 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:55:54 docean postfix/smtpd[5002]: warning: unknown[192.168.1.2]: SASL LOGIN authentication failed: authentication failure
Mar 22 12:55:54 docean postfix/smtpd[5002]: lost connection after AUTH from unknown[192.168.1.2]
Mar 22 12:55:54 docean postfix/smtpd[5002]: disconnect from unknown[192.168.1.2]
Mar 22 12:55:56 docean postfix/smtpd[5002]: connect from unknown[192.168.1.2]
Mar 22 12:55:56 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:55:56 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:55:56 docean postfix/smtpd[5002]: warning: unknown[192.168.1.2]: SASL LOGIN authentication failed: authentication failure
Mar 22 12:55:56 docean postfix/smtpd[5002]: lost connection after AUTH from unknown[192.168.1.2]
Mar 22 12:55:56 docean postfix/smtpd[5002]: disconnect from unknown[192.168.1.2]
Mar 22 12:55:56 docean postfix/smtpd[5002]: connect from unknown[192.168.1.2]
Mar 22 12:55:56 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:55:56 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:55:56 docean postfix/smtpd[5002]: warning: unknown[192.168.1.2]: SASL LOGIN authentication failed: authentication failure
Mar 22 12:55:56 docean postfix/smtpd[5002]: lost connection after AUTH from unknown[192.168.1.2]
Mar 22 12:55:56 docean postfix/smtpd[5002]: disconnect from unknown[192.168.1.2]
Mar 22 12:55:57 docean postfix/smtpd[5002]: connect from unknown[192.168.1.2]
Mar 22 12:55:57 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:55:57 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:55:57 docean postfix/smtpd[5002]: warning: unknown[192.168.1.2]: SASL LOGIN authentication failed: authentication failure
Mar 22 12:55:57 docean postfix/smtpd[5002]: lost connection after AUTH from unknown[192.168.1.2]
Mar 22 12:55:57 docean postfix/smtpd[5002]: disconnect from unknown[192.168.1.2]
Mar 22 12:55:57 docean postfix/smtpd[5002]: connect from unknown[192.168.1.2]
Mar 22 12:55:57 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:55:57 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:55:57 docean postfix/smtpd[5002]: warning: unknown[192.168.1.2]: SASL LOGIN authentication failed: authentication failure
Mar 22 12:55:57 docean postfix/smtpd[5002]: lost connection after AUTH from unknown[192.168.1.2]
Mar 22 12:55:57 docean postfix/smtpd[5002]: disconnect from unknown[192.168.1.2]
Mar 22 12:55:57 docean postfix/smtpd[5002]: connect from unknown[192.168.1.2]
Mar 22 12:55:57 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:55:57 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:55:57 docean postfix/smtpd[5002]: warning: unknown[192.168.1.2]: SASL LOGIN authentication failed: authentication failure
Mar 22 12:55:57 docean postfix/smtpd[5002]: lost connection after AUTH from unknown[192.168.1.2]
Mar 22 12:55:57 docean postfix/smtpd[5002]: disconnect from unknown[192.168.1.2]
Mar 22 12:55:57 docean postfix/smtpd[5002]: connect from unknown[192.168.1.2]
Mar 22 12:55:57 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:55:57 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:55:57 docean postfix/smtpd[5002]: warning: unknown[192.168.1.2]: SASL LOGIN authentication failed: authentication failure
Mar 22 12:55:57 docean postfix/smtpd[5002]: lost connection after AUTH from unknown[192.168.1.2]
Mar 22 12:55:57 docean postfix/smtpd[5002]: disconnect from unknown[192.168.1.2]
Mar 22 12:55:58 docean postfix/smtpd[5002]: connect from unknown[192.168.1.2]
Mar 22 12:55:58 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:55:58 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:55:58 docean postfix/smtpd[5002]: warning: unknown[192.168.1.2]: SASL LOGIN authentication failed: authentication failure
Mar 22 12:55:58 docean postfix/smtpd[5002]: lost connection after AUTH from unknown[192.168.1.2]
Mar 22 12:55:58 docean postfix/smtpd[5002]: disconnect from unknown[192.168.1.2]
Mar 22 12:55:59 docean postfix/smtpd[5002]: connect from unknown[192.168.1.2]
Mar 22 12:55:59 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:55:59 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:55:59 docean postfix/smtpd[5002]: warning: unknown[192.168.1.2]: SASL LOGIN authentication failed: authentication failure
Mar 22 12:55:59 docean postfix/smtpd[5002]: lost connection after AUTH from unknown[192.168.1.2]
Mar 22 12:55:59 docean postfix/smtpd[5002]: disconnect from unknown[192.168.1.2]
Mar 22 12:56:00 docean postfix/smtpd[5002]: connect from unknown[192.168.1.2]
Mar 22 12:56:00 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:56:00 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:56:00 docean postfix/smtpd[5002]: warning: unknown[192.168.1.2]: SASL LOGIN authentication failed: authentication failure
Mar 22 12:56:00 docean postfix/smtpd[5002]: lost connection after AUTH from unknown[192.168.1.2]
Mar 22 12:56:00 docean postfix/smtpd[5002]: disconnect from unknown[192.168.1.2]
Mar 22 12:56:00 docean postfix/smtpd[5002]: connect from unknown[192.168.1.2]
Mar 22 12:56:00 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:56:00 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:56:00 docean postfix/smtpd[5002]: warning: unknown[192.168.1.2]: SASL LOGIN authentication failed: authentication failure
Mar 22 12:56:00 docean postfix/smtpd[5002]: lost connection after AUTH from unknown[192.168.1.2]
Mar 22 12:56:00 docean postfix/smtpd[5002]: disconnect from unknown[192.168.1.2]
Mar 22 12:56:00 docean postfix/smtpd[5002]: connect from unknown[192.168.1.2]
Mar 22 12:56:00 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:56:00 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:56:00 docean postfix/smtpd[5002]: warning: unknown[192.168.1.2]: SASL LOGIN authentication failed: authentication failure
Mar 22 12:56:00 docean postfix/smtpd[5002]: lost connection after AUTH from unknown[192.168.1.2]
Mar 22 12:56:00 docean postfix/smtpd[5002]: disconnect from unknown[192.168.1.2]
Mar 22 12:56:00 docean postfix/smtpd[5002]: connect from unknown[192.168.1.2]
Mar 22 12:56:00 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:56:00 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:56:00 docean postfix/smtpd[5002]: warning: unknown[192.168.1.2]: SASL LOGIN authentication failed: authentication failure
Mar 22 12:56:00 docean postfix/smtpd[5002]: lost connection after AUTH from unknown[192.168.1.2]
Mar 22 12:56:00 docean postfix/smtpd[5002]: disconnect from unknown[192.168.1.2]
Mar 22 12:56:01 docean postfix/smtpd[5002]: connect from unknown[192.168.1.2]
Mar 22 12:56:01 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:56:01 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:56:01 docean postfix/smtpd[5002]: warning: unknown[192.168.1.2]: SASL LOGIN authentication failed: authentication failure
Mar 22 12:56:01 docean postfix/smtpd[5002]: lost connection after AUTH from unknown[192.168.1.2]
Mar 22 12:56:01 docean postfix/smtpd[5002]: disconnect from unknown[192.168.1.2]
Mar 22 12:56:01 docean postfix/smtpd[5002]: connect from unknown[192.168.1.2]
Mar 22 12:56:01 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:56:01 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:56:01 docean postfix/smtpd[5002]: warning: unknown[192.168.1.2]: SASL LOGIN authentication failed: authentication failure
Mar 22 12:56:01 docean postfix/smtpd[5002]: lost connection after AUTH from unknown[192.168.1.2]
Mar 22 12:56:01 docean postfix/smtpd[5002]: disconnect from unknown[192.168.1.2]
Mar 22 12:56:01 docean postfix/smtpd[5002]: connect from unknown[192.168.1.2]
Mar 22 12:56:01 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:56:01 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:56:01 docean postfix/smtpd[5002]: warning: unknown[192.168.1.2]: SASL LOGIN authentication failed: authentication failure
Mar 22 12:56:01 docean postfix/smtpd[5002]: lost connection after AUTH from unknown[192.168.1.2]
Mar 22 12:56:01 docean postfix/smtpd[5002]: disconnect from unknown[192.168.1.2]
Mar 22 12:56:01 docean postfix/smtpd[5002]: connect from unknown[192.168.1.2]
Mar 22 12:56:01 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:56:01 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:56:01 docean postfix/smtpd[5002]: warning: unknown[192.168.1.2]: SASL LOGIN authentication failed: authentication failure
Mar 22 12:56:01 docean postfix/smtpd[5002]: lost connection after AUTH from unknown[192.168.1.2]
Mar 22 12:56:01 docean postfix/smtpd[5002]: disconnect from unknown[192.168.1.2]
Mar 22 12:56:02 docean postfix/smtpd[5002]: connect from unknown[192.168.1.2]
Mar 22 12:56:02 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:56:02 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:56:02 docean postfix/smtpd[5002]: warning: unknown[192.168.1.2]: SASL LOGIN authentication failed: authentication failure
Mar 22 12:56:02 docean postfix/smtpd[5002]: lost connection after AUTH from unknown[192.168.1.2]
Mar 22 12:56:02 docean postfix/smtpd[5002]: disconnect from unknown[192.168.1.2]
Mar 22 12:56:02 docean postfix/smtpd[5002]: connect from unknown[192.168.1.2]
Mar 22 12:56:02 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:56:02 docean postfix/smtpd[5002]: warning: SASL authentication problem: unable to open Berkeley db /etc/sasldb2: No such file or directory
Mar 22 12:56:02 docean postfix/smtpd[5002]: warning: unknown[192.168.1.2]: SASL LOGIN authentication failed: authentication failure
Mar 22 12:56:02 docean postfix/smtpd[5002]: lost connection after AUTH from unknown[192.168.1.2]
Mar 22 12:56:02 docean postfix/smtpd[5002]: disconnect from unknown[192.168.1.2]
Mar 22 12:56:12 docean postfix/smtpd[5002]: connect from unknown[192.168.1.2]
Mar 22 12:56:12 docean postfix/smtpd[5002]: lost connection after CONNECT from unknown[192.168.1.2]
Mar 22 12:56:12 docean postfix/smtpd[5002]: disconnect from unknown[192.168.1.2]

You can start by telling us your requirements. You say you need to relay mail through your ISP. Does the isp require authentication? If not, all you need is to set the relayhost parameter. You should be familiar with the postfix documentation, at the very least this and this. If your ISP requires authentication, then you should also read this. Note if your ISP requires authentication, you need to turn on SASL on the client and not on the server, as you have it.

Also, what's /etc/sasldb2? If this has your credentials for your isp, did you postmap it to create the database?

Hey, billymayday. sasldb2 is a cyrus thing (its form of a passwd file), so not relevant here -- hopefully.

Doesn't it have to be an issue given the number of logged failures?

For sure. I was just saying that the cyrus passwords business isn't necessary for client auth. There's gonna have to be some adjustment to the config.

Raidmax, typically if you are relaying through your ISP, you shouldn't need to authenticate since your IP should be on their relay list. When they gave you instructions to connect a mail client (Outlook, etc), I assume they said to connect your incoming mail to something like pop.eathlinks.com and your outgoing to smtp.earthlinks.com.

In this case, in /etc/postfix/main.cf, you should simply add

relayhost = smtp.earthlinks.com

End of story.

All of those maillog entries look like a PC on your LAN trying to connect and failing.

Can you send mail from the server? Try something like mail -s test some_account@example.com

where some_account@example.com is an external email account you can check (work, hotmail, something like that). Don't try and connect with a mail client from any other machine or you are going to get the errors you see above.