If they are using Google Apps, then the behaviour you have had reported to you 
is to be expected.
Google will change the header to match the authenticated user account. 
Therefore to send email you have two options. 
1. Use an SMTP relay, either from the ISP or purchase the service.
2. If they can get a static IP address, set the PTR etc with a host name that 
resolves to the IP address. That would usually be remote.example.com to keep 
SBS happy.

SPF isn't such a huge issue that everyone says it is, and can cause more 
problems than it resolves. 

On the server in general, run the SBS BPA against the system and ensure it 
comes up clean. If it is SBS 2003 R2 then it may have the older version of WSUS 
on it, which should be installed. Although I would run it against Microsoft 
Update to ensure it has everything - although you will need to do Exchange 
service pack manually if it isn't installation. 

Simon.


--
Simon Butler
MVP: Exchange, MCSE
Sembee Ltd.

e: [email protected]
w: http://www.sembee.co.uk/
w: http://exchange.sembee.info/
w: http://blog.sembee.co.uk/

Need cheap certificates for Exchange, compatible with the iPhone?
http://CertificatesForExchange.com/ for certificates from just $26.99.
Need a domain for your certificate? http://DomainsForExchange.net/ 

Exchange Resources: http://exbpa.com/ 



-----Original Message-----
From: Kurt Buff [mailto:[email protected]] 
Sent: 08 May 2012 06:03
To: NT System Admin Issues
Subject: Re: A new side job - and a few questions...

On Mon, May 7, 2012 at 5:10 PM, Andrew S. Baker <[email protected]> wrote:
>
> Why will you get them down to one provider?
>
> How are the providers being used?

Trust ASB to ask interesting questions :)

The owner is trying to transition away from a Frontier DSL connection
that is too slow, over to an Integra connection that is faster. They
both have fixed IP addresses.

On the Integra connection they have a machine that's dedicated to a
specific function that might (or might not, I haven't had a chance to
look yet) need that fixed address.

They are currently using Google to host their domain, and their
inbound email is forwarded through Google to their SBS server. For
some as yet unknown reason, the owner doesn't want to have email
inbound direct to their SBS server - he's a bit phobic on the matter.
Outbound email is sent over the Frontier link to Frontier's SMTP
infrastructure. The owner isn't happy with Frontier anyway, so he
wants out. Unfortunately, Google (according to the owner) won't relay
- it will only accept outbound for a single user account. I need to
verify this. It seems reasonable to me that it should accept TLS relay
connections for the domain outbound, and not try to make them all
appear to come from one account, but I've seen more stupid things than
that, so...

So, I have to set up their DNS with proper DNS entries (including SPF)
so that the SBS server can send direct, rather than relaying through
as ISP. Not a big deal - it just has to be done.

Kurt

~ Finally, powerful endpoint security that ISN'T a resource hog! ~
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