Multiple SMTP connectors SBS Exchange 2003

I believe this problem has been hashed over before but I don't understand why it will not work properly. I have a client with a SBS 2003 server. Because of a email compliance issue I need to send mail thru their trusted mail host. Each email user must send using their own username and password to send mail thru this host so the mail will be archived properly additionally they reject mail if sender, username and password do not match. I have set up multiple SMTP connectors for each user (each with the appropriate credentials and verified they work by themselves by setting the cost higher on all other connectors), I set the same SMTP cost of 1. I have set delivery restrictions so that each connector will reject mail from all but accept mail from the intended user. I have edited the registry for

HKLM\SYSTEM\CurrentControlSet\Services\RESvc\Parameters\CheckConnectorRestrictions to 1 (DWORD)

and restarted the server. It works at first but then falls apart with NDR's like the one below.

You do not have permission to send to this recipient.  For assistance, contact your system administrator.
            <xxxxxxxxxxxxxx.com #5.7.1 smtp;550 5.7.1 Client does not have permissions to send as this sender>

I wish there was a 3rd party utility to fix this or if it would just work as advertised that would be great.

Please help,
Thanks

It appears to start ignoring the delivery restrictions at some point and going through the wrong connector. Why would this be. There must be a way to fix this.
itmtAsked:
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Alan HardistyConnect With a Mentor Co-OwnerCommented:
Exchange is unable to send out mail via a connector based on the sender.  You can only configure SMTP Connectors to route mail based on the destination domain name and nothing else.
What you are trying to do is completely impossible.
The only way around what you are trying to do is to stop using Exchange to send out mail and use SMTP via your Trusted Mail Host for these emails.  Exchange is not going to be able to do this for you.
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itmtAuthor Commented:
The customer will not abandon exchange period. The problem is with delivery restrictions and according to microsoft articles it should work but is processor intensive. The restrictions work at first but then are simply ignored. I would think there is a 3rd party smtp connect similar to the pop connectors that are available.
Hopefully someone else will have an idea on how this can be accomplished.
Your post is very discouraging. I sure hope you are wrong.
Thanks
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Alan HardistyCo-OwnerCommented:
I'm sorry it is discouraging - but that is the way Exchange is designed.  No amount of tinkering will let you send mail down one particular connector based on the sender, only the recipient domain.
This is a question that pops up lots of times on EE and the answer is always the same.
You can wait for other experts to offer different advice, but you will be wasting your time I'm afraid.
Sorry
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Alan HardistyCo-OwnerCommented:
I'm also not suggesting you scrap Exchange, but if ALL your mail has to go out this way, then you will have to route it via SMTP on the clients and not via Exchange.
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itmtAuthor Commented:
This would defeat the purpose as you would not be able to see your sent mail on any machine you logged into. We use exchange so it doesn't matter which computer they use, laptop, office, home office or any one of the other 5 computers available. I won't be holding my breath but I still believe their is a way.

Thanks
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Alan HardistyCo-OwnerCommented:
Please read the comment from Simon Butler (Mestha) who is MCSE and Microsoft Exchange MVP:
http://www.experts-exchange.com/Software/Server_Software/Email_Servers/Exchange/Q_24595867.html
This relates to Exchange 2007 and if it is not possible in 2007, it certainly won't be available in 2003!
 
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Alan HardistyCo-OwnerCommented:
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Glen KnightConnect With a Mentor Commented:
Alan is absolutely right.

The way the SMTP Connectors are evaluated are based on address space and cost.

If your message fits both of these criteria it will be submitted for delivery.  Once submitted it will be rejected in the form if an NDR if you don't have permission to send using that connector.

I'm not sure what Microsoft documentation you have seen but it's wrong.
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itmtAuthor Commented:
I have not given up yet so I like to keep this open for awhile.
Would it be possible to write a prefilter in VB script or something similar to control the flow of emails?
Any possible 3rd party plug-in or patch?
There must be some way to programmatically do this...
Any ideas would be greatly appreciated.

Thanks,
Dave
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Glen KnightCommented:
It's not possible, I knowany exchange guys/gals that have tried it, myself included.

It's notmpossible without seeing what you have already seen caused by the valuation cycle I mentioned in my previous post.
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itmtAuthor Commented:
I am still looking for some alternative solution to my question. No one has posted a solution nor has anyone suggested anything that might me tried. I do not want to abandon the question so I am not sure how to leave this. Perhaps someone will someday write their own SMTP connector that will solve this issue.
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Glen KnightCommented:
You are not going to get a different answer.
It is not possible.  Sometimes this is the correct answer.
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itmtAuthor Commented:
Since there appears to be no solution at hand I will close this question.
Thanks for all your responses.
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Glen KnightCommented:
You were provided with 2 correct answers first by Alanhardisty and then by myself.

Just because the answers provided were not what you wanted to hear does not make them wrong.
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itmtAuthor Commented:
It was not a solution.
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Glen KnightCommented:
It IS the correct answer!
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