How to use sbs2008 to send via BT or NTLWORLD


I've just installed a workling sbs2008.
That is, I can send and receive emails hapily - ISH !!!

the pop3 connectors work fine.

the hub transport send connector will not send via ntlworld and/or bt.

logs from the connector show it sending EHLO
and getting back assorted settings including 8bitmime
and then simply giving up with a quit.

ideas ?

Who is Participating?
Alan HardistyConnect With a Mentor Co-OwnerCommented:
Outbound mail any only be routed based on the recipient domain as Demazter has already stated.  Exchange cannot route based on sender, so if you have twin Internet connections, you either need to send out via one route or the other (or both) but his can only be configured based on the recipient domain.

Depending on your router, you can either send out via load balancing, which means you don't have much control over which ISP you use, or you setup one as primary and one as failover.

If you setup two outbound connectors using smarthosts, and you load-balance, you have no control over which ISP will be used at any given time, which means mail will sometimes go, sometimes fail.

If you use primary and failover, then you will be fine most of the time until you failover and then you will get failures.

Is this somewhere close to what you are trying to do?
Glen KnightCommented:
Are you running through the smart host wizard in the SBS console?
Well you will only be permitted to send via your ISP usually (unless you authenticate to another smarthost provider).

So, if it is BT you need to register your domain with them usually before you can relay mail using your domain. If Virgin Media, then you need to authenticate with the smarthost.

Did you follow the routine detailed here:

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If your organization has a need to mass-create AD user accounts, watch this video to see how its done without the need for scripting or other unnecessary complexities.

Alan HardistyCo-OwnerCommented:
Are you talking about sending mail to BT and NTLWorld or are you trying to use them as a Smart Host?
If you can't send mail to them, please read my FAQ which might help work out why: 
Glen KnightCommented:
Also do BT or NTLWorld allow you to relay with them? Who is your ISP?

You may have to configure the send connector to use porr 587? If so see here:
noel-nthsAuthor Commented:
thanks for the assorted responses so far.

I can currently send thru a 3rd smart host that i've configured and authenticated

I have both ntlworld and btconnect email addresses
i want to use smart host(s) connected to those isp's (and will then worry about routing relevant outgoing emails thru the correct smart host)

the domain that i configured when setting up the sbs is a dummy

does that answer your queries for extra info.

Glen KnightCommented:
If your not using Btconnect or NTL World as ISP's then you will need to authenticate with them.
You will also need to setup a domain name with them for relaying.

You cannot simply send messages to their smarthost and they will relay them for you otherwise this would be ab open relay.
noel-nthsAuthor Commented:

they detect "relaying" when the mail-from command is sent within the smtp protocol
it doesnt get that far.

my internet conections (two, one via the phone line and a router that "logs into" the bt broadband, and the other via the hardware dedicated cablce network for ntlworld/virgin)

as such, neither of them require authentication (ie a specific logon) to send emails thru them.
they check the mail-from

i've been playing wtih telnet conenctions to them and have noted that the 250-ok does not come back from either bt or ntl (as it does with my other smart host that does require authentication).
i suppose that the lack of 250-ok will then cause the hub-transport to time-out and hence quit.

so, i think my question has become two-fold
1. how to configure the hub-transport smart host to not expect authentication
2. how to route outgoing emails to specific smart hosts based on fropm address

i think we're getting there...
Glen KnightCommented:
1. The send connector by default doesn't require you to use authentication so if you don't specify it when you create the connector then it won't use authentication.

2. You cannot.  There is no reliable way to route e-mail based on the from address to different connectors.
noel-nthsAuthor Commented:

re 1. ok, that's the easy bit

re 2. nuts, when you say "reliable" does that mean you "may" know of a sneaky way ?
or was the "you cannot" definitive ?

Exchange routes based on recipient address not sender address.

Forget Exchange if you are unable to telnet then you have a more fundamental problem with your smarthosts.

Do you have a PTR or reverse DNS record configured for your public IP address (assuming it is a static IP), if so, why not just route directly using DNS?

If you want to use smarthost, then you will need to find out which one will accept your mail. BT business services will normally require you to register your domain with them. See,2003,2045

As for virgin media, they usually require you to authenticate.

Email servers should always accept the MAIL FROM portion of an SMTP conversation if they are configured to accept anonymous mail, it is only when you provide the RCPT TO that it knows if you are trying to submit to a local store or relaying to a remote party, in any caseif it does not provide a successful 2xx , or unsuccessful 4xx or 5xx response, there is a problem. It is likely to be Anti-spam / firewall\router interference causing that.

noel-nthsAuthor Commented:
hi Shaun

no internet problem, you misunderstand.
the telnet works fine.

also, there is no actual domain to register with bt or anyone else.

also, neither bt nor ntlworld (via cable network) will accept anonymous emails.
and i have 2 email addresses, eg fred.bloggs@btconnect and fred.bloggs@ntlworld

if i receive an email on the bt address, i cannot reply to it via the ntlworld smart host
and vice versa

also, although (in general) an isp can be requested to relay for another mail-from domain, that relay is not allowed when the domain is actually another isp.

thanks anyway.

noel-nthsAuthor Commented:
well yes,
unfortunately, it appears to be impossible

which means that the only way to have two source email addresses,
is to route via a 3rd smart host that accepts anonymous emails

thanks to all you guys for your help

even just knowing that it cannot be done is a result
not the one I wanted
but the world isnt perfect

noel-nthsAuthor Commented:

Microsoft Sucks :-)
Alan HardistyCo-OwnerCommented:
When you say "two source email addresses", it is possible to send out from the server as multiple different email domains, the problem is the two connectors to send via a particular ISP at a given time if you have two internet connections.

If you have one connection, not a problem.  The problems appear when you introduce a 2nd and want to be specific about which outbound connector to use as Exchange has no idea about which ISP Is active and working.
noel-nthsAuthor Commented:
although it worse, cos both are active and working....

the issue is about having two smart hosts, and the need to specify which host the email goes via, based on the source address.

and that necessity arises when each email addresses is for one of the "domains" of the isp such that neither will relay the others emails.

the hub allows for the setting up of a transport-rule which can identify the email source address (as containing the relevant domain name),
but the rule doesn't have any "action" that can be used to force the routing via a specific smart host.


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