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Mail delivery fails: "Must issue a STARTTLS command first"

Posted on 2008-02-11
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Last Modified: 2013-11-30
I've a running Exchange (SBS) on pc-manden.net. But I'm so far been unable to recieve any mail, everything is bounceed with the message:
"PERM_FAILURE: SMTP Error (state 12): 530 5.7.0 Must issue a STARTTLS command first"

It has something to do with the security measures, but I've tried following several guides, none of them helped me.
As far as I can tell this is only part of the problem, because I get several other 'wrongs' when checking the domain with different tools. One said that there where no MX record at this domain, but that isn't true. It's there and it's defined in the DNS...
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Question by:ellegaard
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Expert Comment

by:suppsaws
ID: 20873714
Hello ellegaard,

Did you follow all the correct steps to make exchange working?
First let SBS install exchange (by default). Also install SP2.
After that you need to get yourself a fixed ip and make the dns records (mail.yourdomain.com which points to that fixed ip). So you will need an MX record and an A-record.
Check your dns settings at dnsstuff for example.
Then you need to RERUN the CEICW (connect to the internet wizard) and create the correct certificate to match the FQDN.

Regards,

suppsaws
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Author Comment

by:ellegaard
ID: 20873961
I think I've done all that and done it correctly - but something has gone wrong...

I did a test on http://www.dnscolos.com/free-dns-report.html and it came back with only one warning:
"Mailserver connection test
HELO, MAIL FROM, RCPT TO, QUIT"  resulted in
"Connect to mailserver mail.pc-manden.net   FAILED (could be greylisting)
Connect to mailserver backup-mx.zitcom.dk   FAILED (could be greylisting)
554 5.7.1 : Relay access denied  "

How do I fix that?
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Author Comment

by:ellegaard
ID: 20873975
Did some checking and found that this could be caused by my naming of the server servername.pc-manden.local. But that was what the SBS guide suggested.
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LVL 21

Expert Comment

by:suppsaws
ID: 20874048
It looks like your mx records are fine.
I can login to your server on port 25 so that also looks fine.
Did you rerun the CEICW and fill in mail.pc-manden.net for the cert?
Did you choose dns te route the mail and use SMTP? Did you fill in the correct domain  name?
The naming of your server is perfect btw.
Are you getting any specific exchange errors in the eventlogs?
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Author Comment

by:ellegaard
ID: 20874149
Certificat issued to www.pc-manden.net - is that a problem? If I want to use Remote Access as well I need the certificat to be made out to the www - or do I?
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suppsaws earned 1000 total points
ID: 20874176
no no, the cert needs to be the FQDN of your server, that is 'mail.pc-manden.net', this has nothing to do with your www record.
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Author Comment

by:ellegaard
ID: 20874215
ok, changed that, it might have solved some other problems but not this one. I still get

PERM_FAILURE: SMTP Error (state 12): 530 5.7.0 Must issue a STARTTLS command first
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Author Comment

by:ellegaard
ID: 20874222
The mailserver test gives me:
Connect to mailserver mail.pc-manden.net   FAILED (could be greylisting)
Connect to mailserver backup-mx.zitcom.dk   FAILED (could be greylisting)
530 5.7.0 Must issue a STARTTLS command first  "

So one down, one more to go...   :-)
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Expert Comment

by:suppsaws
ID: 20874347
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Author Comment

by:ellegaard
ID: 20874542
Had read that but didn't find anything usefull. Checked my ESMTP verbs, they seem to be ok, but I don't understand why I should wnat to turn them off?
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Author Comment

by:ellegaard
ID: 20874549
You can see my comments in the bottom of the thread as I posted them the in wrong place...  :-)
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Author Comment

by:ellegaard
ID: 20874625
I must have had several errors cause now I found this (http://www.webservertalk.com/archive128-2006-10-1716814.html) as the solution. And I KNOW that I have tried it with it turned off as well.
But my problem is solved as it seems to work now.
Thx for your help
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Expert Comment

by:suppsaws
ID: 20874690
ellegaard,

so what did you change actually now that it works?
I think the CEICW solved it.

suppsaws
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Author Comment

by:ellegaard
ID: 20874762
the changed certificat definantly helped! Butthe last problem was caused by my faulty choice in insisting on encrypted communication

so point are coming your way - thank you!
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LVL 21

Expert Comment

by:suppsaws
ID: 20874787
where did you put the encrypted communication?
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Author Comment

by:ellegaard
ID: 20874948
Well, more like Secure Communication. See this http://www.webservertalk.com/archive128-2006-10-1716814.html
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LVL 21

Expert Comment

by:suppsaws
ID: 20874975
One general tip, only use the wizards in sbs, never do anything manual or you will get into problems.
The whole exchange is configured for you with the CEICW wizard.
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Author Comment

by:ellegaard
ID: 20875060
but only with one domain. Not problem yet, but it will be soon...
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