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Exchange with Windows Small Business Server 2003 using ISP email with exchane features

Posted on 2007-04-09
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I have a customer that has a windows 2003 small business server.  They want to use Exchange but do not want to host their email.   So basically exchange is the mail box store and they utilize cal sharing and contacts.   We hav their POP 3 mail server settings setup as the default mail,  with exchange setup as the profile.  When they send email it sometime's is sent from domain.local,  where it should be domain.com if it was using their outside ISP.  Obviously people cannot reply to domain.local.  Also Ical's default to exchange and they can go up to account and select the isp and it seems fine.  If they forget they are out of luck.  
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Question by:sb020397
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Expert Comment

by:AdamRobinson
ID: 18879850
?

Did you re-run CEICW?
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Author Comment

by:sb020397
ID: 18879856
What is CEICW?
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Expert Comment

by:Erik Pitti
ID: 18879874
First off, I'll assume the users SBS and ISP email aliases match, meaning user1@domain.local = user1@example.com.

My recommendation is to edit the Exchange recipient policy and add an domain entry for @example.com and make @example.com the default.  Mail sent to each-other will not leave the Exchange server and mail sent to the internet will always be from user1@example.com so replies (and iCal) will work properly.

How to use recipient policies to control e-mail addresses in Exchange 2003 and in Exchange 2000
http://support.microsoft.com/kb/319201
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by:Erik Pitti
ID: 18879878
CEICW=Configure E-Mail and Internet Connection Wizard:

http://www.sbs-rocks.com/sbs2k3/sbs2k3-n2.htm
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Author Comment

by:sb020397
ID: 18881440
This client has two offices that use the same outside mail domian.  How is this going to work.  If we add their email domain to their exchange server in location a  what happens when they send to another user of the company in location B since the email domain is the same but that users in location B don't live on the exchange server of location A?
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Expert Comment

by:Sembee
ID: 18881549
Exchange is designed to be responsible for all email for a domain.
Furthermore the POP3 connector is not designed as a long term solution - it is designed to help you move to SMTP delivery, which is how Exchange is designed to work.

While it is possible to get Exchange to work with another site collecting email from the ISP, it is fiddly and not something that I would recommend.

Your best option is to use Exchange as it was designed. Get all email delivered to the SBS server and get users on the other site to collect email from the SBS Server. It will be much easier to manage and everyone can benefit from Exchange feature set.

Simon.
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by:sb020397
ID: 18881685
I agree with you although that is not going to work in this situation.   We have 45 users in the other location and they won't spend that kind of money on cal's, plus then need virus protection and spam protection which is being provided by the email host.
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by:Sembee
ID: 18881745
I would drop Exchange then.
Exchange is primarily an email server and wants to be responsible for all email for the domain. With those sorts of numbers there would be benefit from going to Exchange for all users, but using Exchange for a small subset of users is never going to work effectively.

Simon.
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Author Comment

by:sb020397
ID: 18881972
I disagree,  this client is a law firm that depends on cal sharing and contacts all 3rd party software is no good.  There has to be a work around or solution.
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AdamRobinson earned 168 total points
ID: 18882306
sb020397,

With all due respect intended, as I know you understand your situation better than any of us will, Simon/Sembee is, at least IMO, by far and away the most knowledgeable person about Exchange Server here.  While you don't ever have to accept anything someone here says on faith, his responses get close to it.  

He is correct that POP3 is considered a transition facility -- especially in SBS -- and is not meant to be a long-term solution to not using Exchange 2003 as it was intended.  While I know it never seems a good solution to abandon something you've paid for, Exchange is intended to work precisely as Simon said.  I dealt with this myself recently on a consulting job that sounded much like what you are experiencing.  They ended up abandoning their Exchange server due to the added headache and time (and money, for me) spent maintaining a non-standard setup for a few users.  They wanted to use POP3, and thus the main purpose of the Exchange server was moot.

If you do choose to go ahead and use the POP3 side of things instead of setting up Exchange how it was intended, you've been given two options on how to do what you want, in the first and second posts respectively.

Regarding your question in the third post, if you want to have two domain servers working together in an SBS Domain, you should set it up properly and have them communicate as member servers -- either through PTPs or through VPN.  That, or have the clients at location B do RPC over HTTPS.

You can continue along this path regarding POP3, but it will come back to bite you eventually, which is precisely what "best practices" try to avoid.

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by:Sembee
ID: 18882490
The work around/solution is to use Exchange as it was designed to.
What you are trying to do is make Exchange do something it doesn't want to do and will cause problems.

I think almost all email servers will have similar issues where you try to share the smtp address space across servers. There are methods that can be used to get it to work but they are very labour intensive and will often give you unexpected side effects. Each time you make a change to a user you may have to change a number of elements manually, in the correct order for things to work.
It gets messy very quickly.

If the client is a law firm then the cost of additional Exchange CALs to do everything correctly will be peanuts, just mean that one of the lawyers will have to stay off the golf course for an extra day to pay for it.

If you do it correctly then Exchange will work fine. The problems start when you try to force it to do something that it shouldn't.

Simon.
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Assisted Solution

by:Erik Pitti
Erik Pitti earned 166 total points
ID: 18885929
I totally agree with AdamRobinson and Sembee's posts.  

At some point the setups that preserve POP3 are going to be more trouble to administer than if you had everything in one place, be it the ISP or Exchange.  I know a solution could be put together a that would work w/o transferring all email to Exchange, but it would be a total nightmare to troubleshoot.  The easiest long-term solution is to get everyone on Exchange.

Here's some pricing information for the SBS 20-pack CALs
http://www.nextag.com/Microsoft-CAL-Per-User-57984558/prices-html
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Author Comment

by:sb020397
ID: 18888897
Ok Point made,  I appreciate you guys taking the time on this.   Discussed with client that do not want to lose their exchange.   Can we do the following,  create client new domain and setup exchange ,  we can then forward all email from the abc.com to new domain.  Here's the catch,  when they send email can it appear as if it came from their original domain?  Also when people reply we would want it to go to abc.com and forward to new domain.
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Author Comment

by:sb020397
ID: 18889339
What if we added their domain name to their exchange server and then used the foward all mail through this connector to the following smart host (their ISP is using merak mail server).  From what I have read it appears it would basically use their isp's mail server as a relay server and the IP for their internet can be trusted on Merak.
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Assisted Solution

by:Sembee
Sembee earned 166 total points
ID: 18890461
As soon as you add the domain to recipient policy Exchange will presume that it is responsible for all email for that domain. In order to get email to to leave Exchange with an email address on that domain you must have the domain in recipient policy.

There is an option in Exchange that stops Exchange presuming it is responsible for all email for the domain, and there are various techniques for sharing the SMTP name space http://support.microsoft.com/default.aspx?kbid=321721

However those methods become labour intensive very quickly and if the size of the users increases or changes frequently become complex to manage.

Simon.
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Author Comment

by:sb020397
ID: 18890902
Once I set foward all mail through this connector to the following smart [ip] it then allowed me to manually add in active directory their email address's using the domain that is outside.  It's working perfectly ...   hopefully this won't cause future problems but I can send email from there and when I reply it goes to the isp when the download through pop 3 it puts it back in their mailbox store.  Only problem I see so far is that web access won't be updated unless their outlook is open.   They VPN for remote access so this won't be a issue.   Thanks for all the comments.
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Expert Comment

by:Erik Pitti
ID: 18894621
Just make sure to keep good notes on the configuration.  It can get pretty hairy.
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by:Computer101
ID: 21066586
Forced accept.

Computer101
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