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Exchange 2010 Split Delivery same domain

Posted on 2010-08-27
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Last Modified: 2012-05-10
Hello Experts,
I have one Exchange 2010 with one domain MyDomain.EDU now all of our students email accounts in Google App, however we would like to move all the staff (employees) to Exchange 2010 and leave the students in Google Apps.
my DNS MX pointing to Google Apps.  And I setup Google Apps to deliver any emails to unknown accounts back to Exchange.
IN Exchange 2010 the Accepted Domains is setup to Internal Domain.
I setup an internet Send connector. I tried the Smart Host which I do not have one and the DNS MX record.
I am able to receive and send emails to Exchange, from outside sources for example me@yahoo.com I can also reply. Also Internal email work from one exchange account to the other.
HOWEVER: If I send an email from Exchange mailbox for example me2@mydomain.edu to a Google app account which using the same domain let say me3@mydomain.edu the message will not deliver.
I followed several articles to try to setup exchange to send all messages to the internet regardless in they are internal or external and could not find a solution for this issue.
Any idea?
Thank you
Roy
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Question by:rfinaly
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Expert Comment

by:Busbar
ID: 33547793
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by:B H
ID: 33547802
i see what you're trying to do

your MX and A records are pointing to google - they have to be.  and unknown accounts go to exchange, meaning staff accounts don't exist at google - which is great

but - exchange won't deliver to the outside world, emails that it is responsible for.  even if the student email addresses don't exist on your server, your server still won't try to route them outside.  not even if you use a smarthost.

the only option is going to be having a domain name for the students, that is not registered in exchange.

the problem is, exchange knows "i am responsible for mydomain.edu" and anything else you try to do, won't route outbound
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by:sunnyc7
ID: 33549625
Bryon - excellent analysis.

Lets look at it from another perspective.

2 exchange servers, 2 locations.
Connected using a connector.
half mailboxes in ex1
others in ex2.

You create a send connector for mailboxes which are not present in your exchange and forward them to the other ex2 and they will receive it.

google apps uses something similar for email delivery, which Roy probably used to set it up in the first place.
https://www.google.com/support/a/bin/answer.py?answer=178267

I will post back if I get something on multi-site exchange / same exchange org.
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by:sunnyc7
ID: 33549630
@bryon & busbar
PS: I love it when you take a stab at questions which others wont.

PS Roy - did you check Busbar's article ?
Looks like a similar scenario.
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by:B H
ID: 33551103
hi sunny, great to see you again - i love it when you appear in questions :)

i didnt realize you did JUST exchange stuff

your link to the google answer is what he's already doing for mail sent from external servers to their domain - it splits fine on the way in... the problem is when sending from his own exchange server to the students on the same domain.  

i can't figure out a way to make the exchange server send that email out to google - i understand an exchange connector would be great between two exchange servers, but i don't know if you can do that with google's servers - maybe though..  quite interesting position the author has here.  i really enjoy the situations that are not typical and are difficult to carve a solution to
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Author Comment

by:rfinaly
ID: 33551367
Hello,
Yes I want over the article today but did not try that YET, I will try this tomorrow and get back to you.
I did not configure the Edge transport is that something you recomend to do?
Now just to make sure I get the article correct, I need to add an additional accepted domain for the same domain name mydomain.edu but for external relay I a assuming, than create send conector for the accepted domain in additional to what I already have, is that correct?
Thank you all Roy
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by:B H
ID: 33551509
see i'm not sure if that's going to create some kind of infinite loop:

your server:  when i get mail for this domain, send it to google
google:  when i get mail for this domain, if the user doesn't exist, send it to [your server]
your server: sends it back to google

hence the loop
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Accepted Solution

by:
sunnyc7 earned 500 total points
ID: 33551510
Nope. dont think so.

- You dont need a edge role.
- You need to add an accepted domain mydomain.edu for *internal relay* - and then create a send connector to Google.
- Check with google what will the smart host auth be.

I think you should see this one
http://technet.microsoft.com/en-us/library/bb676395(v=EXCHG.80).aspx

and this one
http://www.google.com/support/a/bin/answer.py?hl=en&answer=178333

I am glad you asked.
The picture in busbar's article looked like it could be a solution, but I think the one above better explains it.

@bryon
check the above article and let me know what you think.

Yep @ just exchange stuff.

Google apps email help page
http://www.google.com/support/a/bin/topic.py?topic=9202
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by:B H
ID: 33551517
no time to check the article, i have no doubt that you would only suggest a working solution :)
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by:sunnyc7
ID: 33551518
@bryon
let me know what you think about my post above.

a) Google will only forward emails out if it *doesnt* find the mailbox in Google Apps, if it's configured as below.
https://www.google.com/support/a/bin/answer.py?answer=178267

b) Internal Relay in Exchange will route emails when it doesnt find email address
http://technet.microsoft.com/en-us/library/bb676395(v=EXCHG.80).aspx

Let me know your thoughts.
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by:sunnyc7
ID: 33551609
My only issue is - I havent tested it..
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Expert Comment

by:sunnyc7
ID: 33551610
I mean - I cant test it.
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by:B H
ID: 33553004
seems like it should work - as long as the internal relay emails are delivered by smtp and not some other transport layer, or tries to use DN's instead of smtp addresses
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Author Comment

by:rfinaly
ID: 33567697
sunnyc7: Sorry for the late reply here, I did try your solution and it is working, however it is working with problems.
So I changed the Accepted Domain to Internal Relay, and I created a new Send connector using Smart Host that uses smtp.gmail.com as the smart host however, I need to authnticate therefore I created in my Google App an account for support@mydomain.edu and I am able to send mail from exchange @mydomain.edu to Google @mydomain.edu but when replying to emails it reply to Support@mydomain.edu.
Is there any outgoing smart host service out there?
Thank you All
Roy
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Expert Comment

by:sunnyc7
ID: 33567776
ok
Whats happening is - whatever account is being used to authenticate to smarthost - that is being used as a reply to.

Is there a corp account for Google Apps. You can try that.

MXToolbox had a smarthost service. I cant seem to find the link for that.
http://www.mxtoolbox.com/Public/Content/Products/

I remember I spoke to someone called Dave
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Author Comment

by:rfinaly
ID: 33571321
sunnyc7: I also tried the administrator account for our domain in Google Apps same results, I contacted Google Support waiting for respond.
Thank you
Roy
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by:sunnyc7
ID: 33571482
ok.
Let us know how that goes.
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Author Comment

by:rfinaly
ID: 33572736
Is there a way to create a smarthost in Exchange/IIIS to relay emails to the internet? I tried the IIS but is goes to the badmail folder.
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by:sunnyc7
ID: 33572740
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Author Comment

by:rfinaly
ID: 33572786
Thank you for the quick reply, what I am looking for it so use IIS as my outgoing relay SMTP server. Do you have an article explaining how to setup IIS to be use as my outgoing SMTP?
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Author Comment

by:rfinaly
ID: 33572897
OR maybe there is a way to configure Exchange 2010 to be outgoing server only. I can install another exchange server on another server and use that as outgoing only?
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Author Comment

by:rfinaly
ID: 33579963
I was able to resolve the issue:
Here is the solution for the issue above:
Create an accepted Domain as Internal Relay.
Create two send connectors.
Send Connector 1: needs to setup as Internet using a smarthost and set the IP for Google.
Send Connector 2: needs to be setup as internal using DNS MX record.
All email from all locations can be relay.
Thank you for all the help exports.
Roy
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by:sunnyc7
ID: 33579997
@Send Connector 2: needs to be setup as internal using DNS MX record.

>> ahaaa !!!
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