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Exchange 2007 HELO

Posted on 2011-05-01
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Last Modified: 2013-11-30
Hi guys,

I am wondering how i activate HELO on an exchange 2007 box i have taken over, part of SBS.

if i telnet it will not accept HELO only EHLO.
all mail is now being forwared from  a mail filter system online, and sends HELO.

Regards
Ben
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Question by:Benji_
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19 Comments
 
LVL 7

Expert Comment

by:wct296
ID: 35500395
Thats weird  EHLO is an ESMTP command whilst HELO is a basic SMTP command  - unless you are disabling basic SMTP...You would think it would be the other way around.. maybe SMTP is being blocked further along - try telneting on the server itself, to itself and see if HELO fails

places I'd check

1) Anti-Spam content/sender filters
2) Check the settings in the receive connector - if in doubt try creating another specific to your IP and see if the default settings allow HELO
3) make sure your FQDN is setup right in the receive and send connectors
0
 
LVL 2

Author Comment

by:Benji_
ID: 35500418
Hi,

Bit  of a twist to this one,

 
220 remote.xxx.com Microsoft ESMTP MAIL Service ready at Sun, 1 May 2011 14:30:20 +0100
HELO UK.com
500 5.3.3 Unrecognized command
HELO uk.com
250 remote.xxx.com Hello [x.x.x.x]

Open in new window


first 1 fails second is ok :S
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LVL 7

Expert Comment

by:wct296
ID: 35500426
ah so its not the command itself.. its the fact that its being case sensitive for the host name/sender domain?
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LVL 2

Author Comment

by:Benji_
ID: 35500430
Nope case doesnt matter,

 
220 remote.mayflowersolicitors.com Microsoft ESMTP MAIL Service ready at Sun, 1 May 2011 14:34:45 +0100
helo uk.com
500 5.3.3 Unrecognized command
helo uk.com
250 remote.mayflowersolicitors.com Hello [x.x.x.x]

Open in new window


I have left unmasked so you can try and see if i am being silly!

ben
0
 
LVL 7

Expert Comment

by:wct296
ID: 35500436
so the first one fails and 2nd attempt passes?
I get the same - even if I do a mistake

220 remote.mayflowersolicitors.com Microsoft ESMTP MAIL Service ready at Sun, 1                                                      May 2011 14:37:47 +0100
helo zenien.com.au
500 5.3.3 Unrecognized command
helo zenien.cpom.au
250 remote.mayflowersolicitors.com Hello [202.89.174.210]
helo zenien.com.au
250 remote.mayflowersolicitors.com Hello [202.89.174.210]

0
 
LVL 2

Author Comment

by:Benji_
ID: 35500444
yep first attempt fails, second passes,

 the helo domain doesnt matter from what i can gather on the internet its just an identifier.

regards
ben
0
 
LVL 7

Expert Comment

by:wct296
ID: 35500445
My only guess is that it the SPF (Sender Policy Framework) causing the issue

This service checks to make sure that the domain you HELO from seems to be correct or somewhat legitimate. It does this by a reverse lookup of the DNS and checks the MX records.

more info here:
http://technet.microsoft.com/en-us/library/bb123557(EXCHG.80).aspx

and how to disable/enable it here
http://technet.microsoft.com/en-us/library/aa997136(EXCHG.80).aspx

Give that a go.. (diable it) and also check that your server can do nice fast DNS queries to the internet and try again
0
 
LVL 2

Author Comment

by:Benji_
ID: 35500455
I have now disabled it on the server, still get the same issue, tried chaning DNS server as well.


also the server the mail is actually coming from for the connection has a valid spf record.

Regards
ben
0
 
LVL 2

Author Comment

by:Benji_
ID: 35500474
* is upgrading to SP3*

0
 
LVL 7

Expert Comment

by:wct296
ID: 35500476
Certainly a weird one.. A quick search for issues where the first helo fails and the 2nd works lead me down the path that a anti-spam or anti-virus program could be attempting to get in on the action at that point and causing a delay or the first HELO failure.. tried disabling any 3rd party apps like that?
0
 
LVL 2

Author Comment

by:Benji_
ID: 35500754
iv upgraded to sp3, i have disabled av and there is no 3rd party apps

so very confused.
0
 
LVL 7

Expert Comment

by:wct296
ID: 35501455
I would delete the receive connectors and re-create using defaults maybe?
0
 
LVL 2

Author Comment

by:Benji_
ID: 35501537
Have just done this and still the same :S

Regards
ben
0
 
LVL 76

Expert Comment

by:Alan Hardisty
ID: 35517476
I just telnetted and issued a HELO command and got a good response the first time I issued the command, so all looks good on your server.

What firewall do you have?
0
 
LVL 37

Expert Comment

by:Jamie McKillop
ID: 35517486
Hello,

Crank up SMTP logging on your server and see what appears in the logs when you try to test. I'd be curious to see what your server is seeing as the command being passed.

JJ
0
 
LVL 17

Expert Comment

by:aoakeley
ID: 35517902
Looks good to me... O reckon you might have fixed it

220 owa.mayflowersolicitors.com Microsoft ESMTP MAIL Service ready at Wed, 4 May 2011 00:31:37 +0100
helo mail
250 owa.mayflowersolicitors.com Hello [  ]
0
 
LVL 2

Author Comment

by:Benji_
ID: 35688730
Humm,

for me im still getting the same problem, i am now going to look through the logs of this.

Regards
ben
0
 
LVL 2

Author Comment

by:Benji_
ID: 35688827

2011-05-04T10:56:31.417Z,SBS2008\Internet,08CDD62AA4C9FD46,4,192.168.2.10:25,193.200.80.44:3715,>,501 5.5.4 Invalid domain name,
2011-05-04T10:56:31.467Z,SBS2008\Internet,08CDD62AA4C9FD46,5,192.168.2.10:25,193.200.80.44:3715,<,HELO mayflowersolicitors.com ,
2011-05-04T10:56:36.472Z,SBS2008\Internet,08CDD62AA4C9FD46,6,192.168.2.10:25,193.200.80.44:3715,>,501 5.5.4 Invalid domain name,
2011-05-04T10:56:36.521Z,SBS2008\Internet,08CDD62AA4C9FD46,7,192.168.2.10:25,193.200.80.44:3715,<,QUIT,
2011-05-04T10:56:36.521Z,SBS2008\Internet,08CDD62AA4C9FD46,8,192.168.2.10:25,193.200.80.44:3715,>,221 2.0.0 Service closing transmission channel,
2011-05-04T10:56:36.521Z,SBS2008\Internet,08CDD62AA4C9FD46,9,192.168.2.10:25,193.200.80.44:3715,-,,Local


I have confirmed the address is in the accepted domain list and i have tried to remove and re-add but it says its attached to users!.

Ben
0
 
LVL 76

Accepted Solution

by:
Alan Hardisty earned 2000 total points
ID: 35689320
Please disable SMTP FIXUP / ESMTP INSPECT on your CISCO router / ASA device and then you may find your problems have gone away.
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