>192.168.10.xxx, [192.168.10.xxx], 9/29/2005, 10:06:23, SMTPSVC1, 
>DURANDAL, 192.168.10.yyy, 0, 20, 319, 250, 0, EHLO, -,  [192.168.10.xxx],
>
>192.168.10.xxx, [192.168.10.xxx], 9/29/2005, 10:06:23, SMTPSVC1, 
>DURANDAL, 192.168.10.yyy 15, 10, 76, 240, 31, QUIT, -, [192.168.10.xxx],
>
>216.165.174.5, OutboundConnectionResponse, 9/29/2005, 10:06:23, SMTPSVC1, 
>DURANDAL, -, 750, 0, 103, 0, 0, -, -, 250 2.6.0  
>-----end-----
>(I've altered the ip's to protect the innocent...)

The irony here is, you altered the private IP range addresses, which 
there is no need to bother, but left the public range IP address in the 
clear. Anything in the 192.168.x.x range you don't have to worry about 
masking because they are not accessable from anyone off your private 
network.

>Notice that I got an 
>"EHLO" followed by a "QUIT" and then another outside IP started talking 
>to the server. This may be reasonable, since the server is not 
>recognizing my "authentication". But it seems strange, nevertheless.

This was done with Emailer?!? That shouldn't be right. Are you sure you 
are looking at the correct log entries? Are you sure the server is 
responding correctly? For Emailer to issue the EHLO followed by a QUIT 
means it didn't get a reply it understood (and in fact, your logs 
indicate no reply was given at all). I just tried telnetting to it, and 
got no reply to EHLO or HELO. That server ain't right.

>Now, looking through the same log, I noticed this entry:
>-----begin-----
>216.165.174.5, OutboundConnectionCommand, 9/29/2005, 10:06:23, SMTPSVC1, 
>DURANDAL, -, 63, 0, 4, 0, 0, EHLO, -, DURANDAL.pecandeluxe.local,
>
>216.165.174.5, OutboundConnectionResponse, 9/29/2005, 10:06:23, SMTPSVC1, 
>DURANDAL, -, 156, 0, 30, 0, 0, -, -, 500 5.3.3 Unrecognized command,
>
>216.165.174.5, OutboundConnectionCommand, 9/29/2005, 10:06:23, SMTPSVC1, 
>DURANDAL, -, 156, 0, 4, 0, 0, HELO, -, DURANDAL.pecandeluxe.local,
>
>216.165.174.5, OutboundConnectionResponse, 9/29/2005, 10:06:23, SMTPSVC1, 
>DURANDAL, -, 234, 0, 56, 0, 0, -, -, 250 mail.clasenqualitycoatings.com 
>-----end-----
>Note that "EHLO" is followed by a "500 5.3.3 Unrecognized command". Could 
>it be that Exchange doesn't do "EHLO"? Seems plausible because the very 
>next line is a "HELO" from the same IP and it is greeted with a "250" 
>response.

Again, this was done with Emailer?!? Again, that shouldn't be right. 
Emailer doesn't retry the welcome command. Nor can Emailer change which 
command it is using (normal Emailer doesn't even know the EHLO command 
exists, and my SMTP Auth hacked version doesn't know the HELO command 
exists).

If you are seeing that in the logs, it wasn't from a connection made by 
any version of Emailer 2.x, hacked or unhacked.

Are you running some kind of a mail proxy? Something that is getting 
between Emailer and your mail server and it possibly screwing up the 
connection?

I can say from the outside world your backup server (bigbrother) is NOT 
SIMS like you said it was... or if it is, it is broken. And from the 
outside world, your main server (assuming the settings you said before 
were accurate and it is smtp.pecandeluxe.com) doesn't point to your 
Exchange server. It points to a Yahoo server (do a DNS lookup on it). And 
it also doesn't reply to a connection attempt from the outside.

Going further with this, durandal.pecandeluxe.com is mapped to the same 
IP address that bigbrother.pecandeluxe.com is mapped to. Telnet to it and 
have a look, something is not right with that server (at least not from 
the outside), the connection response is all screwed up. When I tried 
going to bigbrother.pecandeluxe.com the other day, it at least replied to 
the HELO as valid (gave me a sequence just like your 2nd log listing)

Methinks your problems are not so much with Emailer talking to Exchange 
as they may be with DNS records being wrong, or something else being 
screwy on your setup.

If you can give more details as to how exactly your mail is setup for 
inside and outside access, then maybe I can help more to get to the 
bottom of it. But from what I can see so far, Emailer is NOT the one 
generating the logs you are seeing on the 2nd logs, although it may be on 
the first logs, but if it is, it is doing it because your server isn't 
responding at all.

>So, is there a way to make Exchange accept the "EHLO" command as well as 
>the "HELO"? Or is this all just a rabbit trail?

I'd dig a little deeper into how things are setup. Something isn't right, 
either it isn't they way you think it is, or you have been way to vague 
or misleading with how things are in your postings here. If you have 
security concerns, I'm happy to take this offlist so you don't have to 
share details with the whole world.

-chris
<http://www.mythtech.net>

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