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Does SMTP Relay Work At All on 2007?

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Does SMTP Relay Work At All on 2007? - 26.Sep.2008 11:40:09 AM   
bookgeek

 

Posts: 3
Joined: 26.Sep.2008
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If so, how?
 
Please forgive the length of this post, I want to make clear exactly what I'm doing...

We have a listserv box that maintains lists independantly of exchange. 
(Exchange based DLs are used for internally authenticated mailboxes)

This listserv needs to be able to relay posts and replies to mailboxes on Exchange, orignally setup (by previous admin) as a Hub.

I have:

1) created a custom SMTP connector (call it LISTSRV FWD)

2) set Network > "Use these local IP addreses to recieve" it to recieve exclusively from the LISTSERV box IP (for ex. 10.10.10.69)

3) set Network > "recieve mail from remote servers..." to the same IP only as above(10.10.10.69)

4) set Permission Groups > "Specify who is allowed to connect..." to both "Anonymous Users" and "Exchange Servers"

(I have also tried "Exchange Servers" only and skipped the next two steps... still to no avail.)

5) then set Authentication > "Specify which security mechanisms..." to both
"TLS" and "Externally Secured"

6) finally, enabled anonymous users via the EMS with:

Get-ReceiveConnector “LISTSERV FWD” | Add-ADPermission -User “NT AUTHORITY\ANONYMOUS LOGON” -ExtendedRights “Ms-Exch-SMTP-Accept-Any-Recipient”
 
...which appears to run without issue.


LISTSERV has a nifty little web interface that allows list users to be registered on the system, but when it attempts to send a confirmation email to...

an internal Exchange based mailbox:  it succeeds...  however if the recipient is
 
an external email address, the LISTSERV admin account (an Exchange authenticated mailbox) recieves the following bounce:

"UNDELIVERABLE: Command Confirmation Request (7F406507)"
 

Delivery has failed to these recipients or distribution lists:


FOO.BAR@HOTMAIL.COM
Your message wasn't delivered because of security policies. Microsoft Exchange will not try to redeliver this message for you. Please provide the following diagnostic text to your system administrator.


Diagnostic information for administrators:

Generating server: LISTSERV.OURDOMAIN.LIB.XX.US

FOO.BAR@HOTMAIL.COM
#< #5.7.1> #SMTP#





Now, can anyone tell me what in the blazes have I done wrong here? 

I have found about three different walkthroughs for this process (the above being the third) and cannot seem to make any of them work?  ID10T error on my part?

Please advise.

_____________________________

--It is an Ill Wind that Blows no Minds...
Post #: 1
RE: Does SMTP Relay Work At All on 2007? - 26.Sep.2008 12:02:39 PM   
John Weber

 

Posts: 1236
Joined: 20.Apr.2005
From: Portland, Oregon
Status: offline
A little further troubleshooting...

What happens when you TELNET from the listsrv server to the IP of the e2k7 recieve connector?
I would like to know what it does.  I suspect that the e2k7 server is simply dropping the connection.  If so, I know how to fix it.

_____________________________

John Weber [Lync MVP] http://tsoorad.blogspot.com

(in reply to bookgeek)
Post #: 2
RE: Does SMTP Relay Work At All on 2007? - 26.Sep.2008 12:37:38 PM   
bookgeek

 

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Joined: 26.Sep.2008
Status: offline
hi John,

Thank you for replying.

Telnet sessions appear to hang, then drop soon after opening.

I also noticed that the first two connectors created (I assume) by my predecessor are bound to ports 587 and 25.

Client Exchange:  587
Default Exchange: 25
LISTSERV FWD: 25

Am I looking at some kind of binding conflict here?

_____________________________

--It is an Ill Wind that Blows no Minds...

(in reply to bookgeek)
Post #: 3
RE: Does SMTP Relay Work At All on 2007? - 26.Sep.2008 12:49:28 PM   
John Weber

 

Posts: 1236
Joined: 20.Apr.2005
From: Portland, Oregon
Status: offline
What you are seeing is the e2k7 does not "approve" of the connection.

E2k7 evaluates the incoming connection on port 25, and if it finds a specific connector that has a set of perms that allow the connection for the source IP, it accepts it.  When it just drops like that, it means that no connector is configured to allow that IP to connect.

Take a look at this here:  http://tsoorad.blogspot.com/2008/01/allowing-application-servers-to-relay.html and see if it helps.

The two default connectors are for internal use.  You should create an internet receive connector just for general use.  What you want is an application connector that uses the externally secured option.  Just make sure that you scope the IP to ONLY that one IP, or you will have indeed created an open relay for anyone to use.

You can have a bazillion connectors; E2k7 will only use the one that pertains to that IP.  Your internet receive connector will not be used if a specific connector is configured for the ListSrv application.

Let me know how it goes.


_____________________________

John Weber [Lync MVP] http://tsoorad.blogspot.com

(in reply to bookgeek)
Post #: 4
RE: Does SMTP Relay Work At All on 2007? - 26.Sep.2008 12:59:44 PM   
bookgeek

 

Posts: 3
Joined: 26.Sep.2008
Status: offline
Excellent.  Thank you.  I'll give this shot. :)

_____________________________

--It is an Ill Wind that Blows no Minds...

(in reply to John Weber)
Post #: 5

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