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Q: Using internal and outsourced e-mail (POP3/SMTP) with Windows 2003 ( No Answer,   2 Comments )
Question  
Subject: Using internal and outsourced e-mail (POP3/SMTP) with Windows 2003
Category: Computers > Internet
Asked by: portman-ga
List Price: $75.00
Posted: 04 Dec 2003 22:38 PST
Expires: 03 Jan 2004 22:38 PST
Question ID: 283732
I have a Windows 2003 Server that is behind a firewall and not
accessible from the Internet. I have outsourced our company's e-mail
to a dedicated host in the USA. So users log on to the Internet to
send and receive e-mail. They can also, if they choose to, log on to
the Win2K3 server to send e-mails on the internal network. I would
like to MERGE these two functions -- right now, users must choose the
mail account from a dropdown menu in Outlook Express ("Internal" or
"External"). I want them to be able to ONLY use the internal Windows
2003 server, and I want that server to automatically forward external
e-mail to our outsourced host.

Here are some fuller details:

The domain is "sub.domain.org". This is a registered domain on the
Internet, with a proper A record and MX record pointing to my
outsouced e-mail host (Swishmail). If someone sends e-mail to
"person@sub.domain.org" then it goes to the Swishmail server where it
waits for a client to download it.

The problem is that whenever someone on the network sends an e-mail to
someone else on the network using the outsourced e-mail server. The
mail has to be sent to Swishmail, and then downloaded again by another
user. This is in Cambodia where Internet access is very slow. That is
why I set up the Windows 2003 POP3/SMTP server role. Then when a user
sends an internal e-mail, they select the Windows server and send it.
The e-mail never neads to leave the building. HOWEVER, sometimes (in
fact, most of the time), the e-mail is to someone outside the company
but also CC-ed to someone inside the company. It is in these cases
that I want to be able to get the best of both worlds: the mail will
be delivered using the Windows server for the internal client but the
outsourced server for the external client. Is this even possible using
only Windows 2003 and not a full e-mail server like exchange? It seems
should be possible , since the rules are very trivial:

 - If the recipient is "sub.domain.org" then keep it on the server and
wait for POP3 pickup by a local client.
 - If the recipient is anything else, then forward it to the
outsourced SMTP server.

I really need a solution quickly, hence the high price for what is (I
imagine) a simple answer.

Thanks!

Request for Question Clarification by endo-ga on 04 Dec 2003 22:59 PST
Hi,

I can give you an answer that requires a third party, free
application. You might need some time learning how to configure it.
But basically it's a POP/SMTP server application, that can forward
mail to different destinations depending on the contents of the email.
It requires Java and MySQL to run.

Please let me know if you're interested.

Thanks.
endo

Clarification of Question by portman-ga on 05 Dec 2003 23:08 PST
I would like a free solution. I realize that this can easily happen by
installing a full-blown POP3/SMTP mail server. But I was hoping to use
the server integrated with Windows Server 2003. If that is not
possible, then free software would be preferred.

Request for Question Clarification by endo-ga on 06 Dec 2003 08:10 PST
Hi,

The POP3/SMTP server I'm thinking of is free, but you will need to get
used to it and take some time to configure it and preferably have some
knowledge of how to use Java and MySQL.

Thanks.
endo

Clarification of Question by portman-ga on 06 Dec 2003 16:35 PST
To Endo:

Thank you for the additionaly clarification. That really isn't what
I'm looking for... the whole reason for outsourcing was to avoid the
difficulties of running our own mail server, and there certainly isn't
any Java expertise on site. Thank you for your time, though.

Request for Question Clarification by endo-ga on 08 Dec 2003 18:10 PST
Hi,

Can you please try the following and let me know how it goes?



1. Start IIS.
2. Right click on "Default Virtual SMTP Server" and select "Properties"
3. Select "Delivery" page and click on "Advanced" button.
4. In "Smart Host" field type the IP address of the Mail Server who hosts
external mail. (Since the internal domain name and external domain name
is same, don't type the FQDN, type the IP address instead, and WITHOUT
brackets "[ ...]".)
5. Save the settings by clicking on  "OK",   "Apply".

That's all. Now you can remove the account "External" from all clients,
and use only "Internal" account.

If an e- mail marked are person@sub.domain.org , the mail server will
deliver them to local accounts (provided the account exists, of course).
If an e-mail is marked to any other domain apart from sub.domain.org, then it
will be delivered to the SMTP server,  having IP addressed mentioned in step 4
above.

Please let me know how it goes.

Thanks.
endo

Clarification of Question by portman-ga on 11 Dec 2003 19:22 PST
Endo:

Although the steps you suggested did not in fact work (I get a
"realying denied" error from the server whenever I send mail to a
non-local domain), you are definitely on to something with the Smart
Hosts.

Here is what I have so far that is nearly working:
- SMTP Server (From IIS), right-click on Domains and add new domain
- Add a remote domain
- In the properties, select "Allow incoming mail..." and "Forward all mail to..."
- I have setup rules like this for 
  *.com
  *.org
  *.net
  *.cc
  *.name
And it is working whenever my users send an e-mail that is NOT on our
domain to an e-mail in one of those TLDs. Obviously, I feel like there
has got to be an easier way than by inputting all 182 TLDs and
maintaining that list. And no, *.* does not work ;-)

Any further pointers? I think this SmartHost thing is totally the way
to go. And since you have almost solved my issue, how does this work
with payment?

Request for Question Clarification by endo-ga on 12 Dec 2003 08:35 PST
Hi,

I'm working on finding a solution, please bear with me for a while,
I'll get back to you as soon as possible.

Regarding payment, until I post an answer you don't have to pay, I
want to make sure you're 100% satisfied, then I'll post a solution as
an answer. I hope that's ok with you.

Thanks.
endo

Request for Question Clarification by endo-ga on 13 Dec 2003 20:34 PST
Hi,

Someone has suggested the following for your problem.

You do not need to add any remote / or local domain in the virtual
SMTP server. In the POP3 server you already created, domain
'sub.domain.org'.
When you do this, the same domain will automatically appear in the
virtual SMTP server, domains ,  as local domain.

2. Delete the new remote  domain (s) you created. Leave the
sub.domain.org, domain, which automatically got added, when you
created the POP3 domain, as it is (so there will not be any remote
domain).

3. Now in IIS right click on 'Default SMTP Virtual server' (which is
listed on the left side, not on domains)  and select Properties.

4. Select "Delivery" page and click on "Advanced"  button.

5. In "Smart Host" field type the IP address of  your ISP's mail server.
(type IP address and not the "sub.domain.org." Save all settings. That's all.

Now since your clients have to download incoming mails from your local
server as well from the ISP's server, you must have two accounts on
the clients, having appropriate pop3 servers (by IP address only,
since the name of both internal and external domain is same).

But for outgoing mails, in both accounts, for SMTP server, give the IP
address of your local server.

Another point to be considered is that, on the ISP's mail server, has ISP
enabled SMTP authentication? i.e. For the existing external mail account on
the clients, check the account properties, Server Tab, in 'Outgoing
Mail server'. Is "My server requires authentication" selected?

If no, then nothing further needs to be done.

If yes then what type of authentication is it?
There are two types. One is the same as for incoming server settings,
the other is log on using (a different) Account name and password.

If the latter, then you go again to 'Default SMTP Virtual Server'
properties, Delivery Tab. There click on Outbound Security. Select
Basic authentication and give the same account name and password as
was given in Outlook Express.

Also on every client you either remove the setting My outgoing server
requires authentication from the external account, since it is now
using your local SMTP server.

On the otherhand, if the authentication settings are same as my incoming
server, then you have a problem. you will have to ask your ISP, to change the
method to basic authentication for SMTP relay, i.e. only one username
and password for all senders, instead of using individuals POP3
username and password.


I hope this helps.

Please let me know how it goes.

Thanks.
endo

Request for Question Clarification by endo-ga on 18 Dec 2003 09:50 PST
Hi,

Have you had any luck with the suggestion?

Thanks.
endo
Answer  
There is no answer at this time.

Comments  
Subject: Re: Using internal and outsourced e-mail (POP3/SMTP) with Windows 2003
From: rkm100-ga on 05 Dec 2003 05:03 PST
 
There could be many options.. one of them is the following..

Jana Server (for commercial use 50 Euro per server)
http://www.janaserver.de/start.php?lang=en&menue=home&content=features

If you have all users in one building, then Jana could do what you are looking :)
Subject: Re: Using internal and outsourced e-mail (POP3/SMTP) with Windows 2003
From: endo-ga on 06 Jan 2004 09:19 PST
 
Hi,

Have you been able to try the suggestion?

Thanks.
endo

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