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SMTP TLS Authentication using Postfix in Leopard

Hi. I used Postfix enabler in Tiger to set up a mail server and recently upgraded to Tiger. I've been getting errors that read:

Transcript of session follows.

Out: 220 [domain_name].com ESMTP Postfix
In: EHLO [192.168.x.x]
Out: 250-[domain_name].com
Out: 250-PIPELINING
Out: 250-SIZE
Out: 250-VRFY
Out: 250-ETRN
Out: 250-AUTH LOGIN PLAIN
Out: 250-AUTH=LOGIN PLAIN
Out: 250-STARTTLS
Out: 250-ENHANCEDSTATUSCODES
Out: 250-8BITMIME
Out: 250 DSN
In: STARTTLS
Out: 454 4.3.0 TLS not available due to local problem

Session aborted, reason: lost connection

Mail logs read:

Jan 16 21:32:46 Mini postfix/smtpd[570]: warning: connect to private/tlsmgr: No such file or directory
Jan 16 21:32:47: --- last message repeated 1 time ---
Jan 16 21:32:47 Mini postfix/smtpd[570]: warning: problem talking to server private/tlsmgr: No such file or directory
Jan 16 21:32:47 Mini postfix/smtpd[570]: warning: no entropy for TLS key generation: disabling TLS support
Jan 16 21:32:47 Mini postfix/smtpd[570]: connect from x-x-x-x.dynamic.[isp].net[x.x.x.x]
Jan 16 21:32:47 Mini postfix/smtpd[570]: lost connection after STARTTLS from x-x-x-x.dynamic.[isp].net[x.x.x.x]

This happens when I try to send an email using my SMTP server. I think it's an easy command such as regenerating the TLS key or something along the lines of that. Any help will be appreciated.

Thank you.

MacBook Pro 15", Mac OS X (10.5)

Posted on Jan 16, 2008 5:43 AM

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Question marked as Best reply

Posted on Jan 21, 2008 8:52 AM

I've had the same issue. This is a problem with a valid SSL cert. You will be forced to use a self-signed cert with no shared secret in order to use SSL for SMTP. You will still be able to use the valid SSL cert however for other services. Which makes no sense. I have been waiting for a response from Apple on the SSL thing for 3 weeks and they have no idea either and only now are replying that in order for me to get an answer I have to upgrade my support. Anyway I hope this helps. Let me know if you here of any other solution to this problem.
3 replies
Question marked as Best reply

Jan 21, 2008 8:52 AM in response to lawrence.wang

I've had the same issue. This is a problem with a valid SSL cert. You will be forced to use a self-signed cert with no shared secret in order to use SSL for SMTP. You will still be able to use the valid SSL cert however for other services. Which makes no sense. I have been waiting for a response from Apple on the SSL thing for 3 weeks and they have no idea either and only now are replying that in order for me to get an answer I have to upgrade my support. Anyway I hope this helps. Let me know if you here of any other solution to this problem.

SMTP TLS Authentication using Postfix in Leopard

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