Force outgoing mail using smtp to internet bypassing internal network routing

Posted on 2008-10-28
Last Modified: 2013-12-18
This one should really test the experts.  I have dual email platforms.  Lotus Domino 6.5.1 and MS Exchange 2007 SP2.  All incoming mail hits a Linux mail proxy (Moxy) and is passed on to each mail
server (Notes and Exchange). We have one domain  My problem is we need to force
outgoing mail to other users from Notes and/or Exchange to send via the internet and bypassing the internal network so wether they are using their Notes client or Exchange client
mail goes to both servers via the proxy.  All of our users have the same email addresses on each
server. As it stands now if a users send email to another user in Notes only the Notes client
receives the email.  Same with Exchange.  I want to force it all out so it comes back and hits the proxy
server where it will go to both platforms.
Question by:lalgarin
LVL 46

Expert Comment

by:Sjef Bosman
ID: 22823578
At first I thought:
- Add an SMTP domain, for,
- Add a Connection document that mentions your proxy as mail relay server
and Bob's your uncle.

But no, I'm afraid this will never work, because it would create a mail loop. All routing to Notes users is based on Notes names. I suppose that you want an internal mail to Foghorn Leghorn/LOONYTUNES to be first transferred to fleghorn (et), then it gets transferred to your gateway, which sees that the mail is local, so then it comes straight back; and then the Domino server would be so smart to find that
fleghorn (et) is in fact our friend Foghorn and transfers the mail to him. Is that it? The server is even smarter: even if I only specify the Internet mailaddress of someone, and that someone is found in the internal address book, the router immediately transfers the mail to the right mailbox.

Could you think of a different scenario that might fit your organisation and requirements?

Author Comment

ID: 22823786
Thanks sjef bosman for your quick responce.
Unfortunately the nature of our business is that a full transition from Notes to Exchange will
take a very long time and some users are never going to want to make the move.  I need to solve
this.  I was elated to get all incoming mail to his our proxy and send the same mail to both Exchange
and Notes.  We are half way there.  Also, in the event of catasrophic failure I can have my users
switch from one client to the other.  I'm going to hold out for a solution until someone tells me this
just absolutely can't be done.
LVL 46

Expert Comment

by:Sjef Bosman
ID: 22824143
Why the Exchange server? Did you know that your Outlook users can use the Domino server as their mail server and still use Outlook to the max? Look for the DAMO product, it stands for Domino Access for Microsoft Outlook.

Just thinking out loud here:
- To send mail from one internal mailbox to the other, you need two different mail addresses.
- Consequence: fleghorn on server1 is NO LONGER fleghorn on server2
- If that is so, you could define each server it its own domain (internally), say and, and you let the gateway have the company domain
- Or just 2 domains, where one of the servers is also the gateway
- This setup would force you to specify somewhere what the real domain is for every user (a pain in the xyz if you have 10,000 of them)

Here's a page that describes a little what your options are:

The DAMO idea isn't explained there (it's an IBM product):
LVL 63

Expert Comment

ID: 22824409
Other option is to tell Notes to always send via SMTP via Internet.

I know that this is an option in the Client, and maybe you can push it out via Domino Policies.

I hope this helps !
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LVL 20

Expert Comment

ID: 22824460
I'm along the lines with sjef on this one.

There are probably several different ways you can try to do this but at a minimum I think you will need to have separate SMTP domains. Even when I used the MS connector a long time ago it created entries in the domino directory with a different notes domain (i.e. Joe User/US/Company@Notes vs. Joe User/US/Company@Exchange) so it could differentiate them in the directory.

When Domino can match an e-mail address with a user in the directory it is going to keep it internally. You can force it to send messages intended for users not found in the directory to a smarthost or proxy but again the server cannot find the name in the address book.

If you can make either domino or exchange be instead of it might make it easier but then you can run into issue as to which address is presented when sending messages and so forth.

Author Comment

ID: 22878932
I understand what sjef and brwwiggins are saying but hope SysExpert is closer to an answer.  As stated originally I have one mail domain. All my users have the same email address in Exchange and Notes i.e.  All incoming email hits my mx mail proxy (Linux) @
and an exact copy is sent to both the Exchange server/inbox and Notes server/inbox.  My problem
is with outgoing mail between internal users where joeblow@xxxxx.xom sends an email to routes to either Exchange only (if sent from Outlook client) or Notes only (if sent from Notes client).  I want all outgoing mail between internal users to go out to the internet so it comes
in through the mx mail proxy thus going to both Exchange and Notes.  Is this do-able?
LVL 46

Accepted Solution

Sjef Bosman earned 500 total points
ID: 22879208
Yep: use webmail... :-))

Or use Internet accounts on the proxy server for all users and send the mail directly there, bypassing the router completely (no Notes-Notes mail, no Exchange-Exchange mail, but EVERYTHING to the proxy). Doable, yes... Maintainable... hmmm...

I don't see any other way.

Author Closing Comment

ID: 31510787
I'm closing the question and accepting sjef bosman's responce as the final answer.  Thanks to everyone for your input.  lalgarin

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