I've been fighting with this problem a bit now. Google and RTFM have been pretty kind to me, and I'm about 90% to having a solution implemented. I've gotten hung up on one little detail, and I find myself in need of some guidance.

I run a RHEL5 server with postfix, clam, spamassassin, & dovecot. About a year or so ago I switched from Sendmail (which I had been running since 1995) to Postfix when I rebuilt my mail server, and it's been a pretty painless conversion. I have discovered a couple of mail servers on the net that will not accept mail from any customer at my ISP ("We're sorry, but the class B that you're coming from is in the MAPS database as being dynamically assigned, so bugger off!" Funny... I've paid for a block of static addresses for 3 years now from my ISP) so I've got to relay mail to a couple of specific domain through my ISP's mail server. Their server admin is a pretty decent guy and generally has a clue and I've got things mostly working. My ISP's mail server is doing non-encrypted SASL for outbound mail on an odd-ball port, (577) and only accepting connections from IP address space allocated to it's customers.

In my main.cf I have this line:
transport_maps = hash:/etc/postfix/transport

in my /etc/postfix/transport I have these two lines: (host/domain names changed to protect the innocent)
foo.com      smtp:[smtp.my-isp.net]:577
.foo.com      smtp:[smtp.my-isp.net]:577

and in /etc/postfix/sasl_password  I have this:
smtp.my-isp.net:577 MyUsernameHere:MyPasswordHere

I have used postmap to hash the transport file and the sasl_password file. When I tail -f /var/log/maillog, and send a test e-mail to someone at foo.com, here's what I see:


Sep 3 20:17:55 perrin postfix/smtp[25264]: certificate verification failed for mail.my-isp.net: num=20:unable to get local issuer certificate Sep 3 20:17:55 perrin postfix/smtp[25264]: certificate verification failed for mail.my-isp.net: num=27:certificate not trusted Sep 3 20:17:55 perrin postfix/smtp[25264]: certificate verification failed for mail.my-isp.net: num=21:unable to verify the first certificate Sep 3 20:17:55 perrin postfix/smtp[25264]: Server certificate could not be verified Sep 3 20:17:57 perrin postfix/smtp[25264]: 0CC783353FA: to=<[EMAIL PROTECTED]>, relay=mail.southslope.net[167.142.226.73], delay=7, status=bounced (host mail.my-isp.net[167.42.226.73] said: 530 [EMAIL PROTECTED] You must authenticate first (in reply to MAIL FROM command)) Sep 3 20:18:01 perrin postfix/cleanup[25211]: 4C44D3353FF: message-id=<[EMAIL PROTECTED]> Sep 3 20:18:01 perrin postfix/qmgr[19404]: 4C44D3353FF: from=<>, size=2703, nrcpt=1 (queue active)
Sep  3 20:18:01 perrin postfix/qmgr[19404]: 0CC783353FA: removed
Sep 3 20:18:01 perrin postfix/local[25254]: 4C44D3353FF: to=<[EMAIL PROTECTED]>, relay=local, delay=0, status=sent (delivered to mailbox)
Sep  3 20:18:01 perrin postfix/qmgr[19404]: 4C44D3353FF: removed


It looks a lot like it's not doing any sort of authentication when trying to connect to the ISP's mail server. Any suggestions? Feel free to suggest something that might seem painfully obvious to you,

Thanks,
  - Micah

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