GW2k3 Exchange connector smtp addressing

Hello all.
I am having some trouble with the exchange connector for Groupwise 7 to exchange 2k3.
What we want to do may be a bit strange and I'm not sure if the connector will even allow us to do this.
We would like to use the connector to sync users between AD and Groupwise however we do not want the connector to handle the mail routing between the systems. What we would like it to do is use the SMTP addresses ([email protected]) instead of the GWISE:Domain.po.username address.
On the Groupwise side of things this seems to have been very easy to setup we just went to the external domain and selected internet addressing and specified that we wanted it to use the [email protected] However the exchange side is proving to be more of a challenge. We have tried setting the recipient policies to use the SMTP address as a primary however the imported contacts inside of outlook still list the primary email address as GWISE:domain.po.username. If we try to remove the GWISE address from the imported users it says that this is the home address of the user and it cannot be removed.
Is there any way to not sync the GWISE address over to AD and just use SMTP? Or is there a way to sync GWISE address but use the SMTP as the primary for all imported users?
If anyone has attempted this or something similar any help would be appreciated.

The whole purpose of the gateway is to route email between the systems.
The addressbook visibility is provided to support this purpose.
If you are just trying to email addressing, then I believe you would
accomplish what you seem to be trying to do by setting up an LDAP addres
book on exchange pointing to eDir, and the reverse in GW.
If you are actually wanting to sync users in both systems, you might want
to consider implementing an IDM.
-jt
On Fri, 13 Jun 2008 13:56:01 +0000, jvandrew wrote:
>
> jvandrew;1577862 Wrote:
>> Hello all.
>> I am having some trouble with the exchange connector for Groupwise 7 to
>> exchange 2k3.
>> What we want to do may be a bit strange and I'm not sure if the
>> connector will even allow us to do this.
>>
>> We would like to use the connector to sync users between AD and
>> Groupwise however we do not want the connector to handle the mail
>> routing between the systems. What we would like it to do is use the SMTP
>> addresses ([email protected]) instead of the GWISE:Domain.po.username
>> address.
>>
>> On the Groupwise side of things this seems to have been very easy to
>> setup we just went to the external domain and selected internet
>> addressing and specified that we wanted it to use the
>> [email protected]. However the exchange side is proving to
>> be more of a challenge. We have tried setting the recipient policies to
>> use the SMTP address as a primary however the imported contacts inside
>> of outlook still list the primary email address as
>> GWISE:domain.po.username. If we try to remove the GWISE address from the
>> imported users it says that this is the home address of the user and it
>> cannot be removed.
>>
>> Is there any way to not sync the GWISE address over to AD and just use
>> SMTP? Or is there a way to sync GWISE address but use the SMTP as the
>> primary for all imported users?
>>
>> If anyone has attempted this or something similar any help would be
>> appreciated.
>
> After further investigation what we are seeing is that the Target address
> inside of exchange is being set to the GWISE address. Is there anyway to
> specify in Exchange or the GroupWise connector to use a different target
> address value such as the SMTP address?

Similar Messages

Problem handling SMTP address with OIM 11gR2 Exchange connector

Hello,
I have a problem in regarding the primary SMTP address with the Exchange connector. The connector doesn't seem to be able to update it. Changing a user's primary SMTP address from its account details in OIM creates a new secondary address in Exchange. It does not change the current primary SMTP address. This does not look like a normal behavior... Any ideas on how to fix this?
I'm using OIM 11gR2 with BP10 with AD 11.1.1.5.0A and Exchange 11.1.1.5.0.
Thanks,
--jtellier

Yes, you can try out few things suggested in below thread
Re: Exchange Provisioning
The error looks like form exchange server side but still not sure about it.
Meantime open Service Request with oracle about the same as I can see other developers are also facing same issue.

Exchange 2010 to 2013 cross forest migration doesn't have an SMTP address that matches the target delivery domain

I’m having a problem moving a mailbox from exchange 2010 sp3 to Exchange 2013 which are in two separate forests.
Two way trust in place
Certificates imported
ADMT is set up.
SMTP namespace oldcompany.org and newcompany.org for the old email domain and new one is configured to be shared between forests.
I’m doing the following:
Step 1
Prepare-MoveRequest.ps1 -Identity [email protected] -RemoteForestDomainController DC1. oldcompany.Local -RemoteForestCredential $RemoteCredentials -LocalForestDomainController DC1. newcompany.local -LocalForestCredential $LocalCredentials -TargetMailUserOU
"OU=Office Users , DC=newcompany,DC=local" –verbose
Everything goes ok, and a disabled user is created. A disabled user account is created in the correct OU.
Email address is set to [email protected]
Proxy smtp addresses are set:
smtp:[email protected]
SMTP:[email protected]
smtp:[email protected]
Step 2
I then use ADMT and migrate sid history ect.
Step 3
New-MoveRequest –Identity [email protected] –Remote –Remotehostname exchange.oldcompany.local -RemoteCredential $RemoteCredentials –TargetDeliverydomain exchange.newcompany.local
This then fails with the error:
The target mail user newcompany.local/Office Users /mark test' doesn't have an SMTP address that matches
the target delivery domain 'exchange.newcompany.local'.
    + CategoryInfo          : InvalidArgument: ([email protected]:MailboxOrMailUserIdParameter) [New-MoveReques
   t], RecipientTaskException
    + FullyQualifiedErrorId : [Server=EXCHANGE,RequestId=ec704dc8-bfb9-47c1-a1ec-cc6d8ef00484,TimeStamp=23/12/2014 1
   0:51:33] [FailureCategory=Cmdlet-RecipientTaskException] 5ABE3B29,Microsoft.Exchange.Management.RecipientTasks.New
MoveRequest
    + PSComputerName        : exchange.newcompany.local
Any ideas what I am missing.

Hi Walkersway,
As you have mentioned both the domains are "shared between forests", I would assume its added to the accepted domains as Internal Relay. Also you have 'Send Connector' Setup to relay out the email to the new forest.
"You configure the SMTP domain as an internal relay domain to make sure that email that's addressed to that domain is accepted by the Exchange organization. The connector configuration of your organization determines how messages are routed."
In your case "newcompany.local" should be present.
Try this:
New-MoveRequest –Identity [email protected] –Remote –Remotehostname exchange.oldcompany.local -RemoteCredential $RemoteCredentials –TargetDeliverydomain newcompany.local
The TargetDeliveryDomain parameter specifies the FQDN of the external email address
created in the source forest for the mail-enabled user when the move request is complete. This parameter is allowed only when performing remote moves with the
Remote or RemoteLegacy parameter.
Regards,
Satyajit
Please “Vote As Helpful”
if you find my contribution useful or “Mark As Answer” if it does answer your question. That will encourage me - and others - to take time out to help you.

OIM Exchange Provision - Primary address (SMTP: vs smtp: proxy address val)

The Exchange provision process completes successfully, but it appears as if the proxyaddress that gets created is NOT for a primary address. This is indicated by the value being prefixed by "smtp:" (lowercase) vs "SMTP:" (uppercase). If I set the primary email on the user form manually it will update and create a primary (uppercase SMTP:) correctly for that same user. Is the behavior of the initial provision an issue with the connector or the Exchange (recipient policies) configuration?
** I'm aware that there is a 9.1.1 version of the Exchange connector that appears to have fixed alot of stuff, but I can't upgrade right now from my 9.1.0.1 version.

I'd have to second Mike Crowley. This is the way it has always been.
Snuffy has a correct email address on his mailbox of [email protected]
Someone comes along and adds [email protected] to his proxy addresses. Now, if someone internal sends a message to [email protected], Exchange consults the Active Directory first to see if any recipients match that SMTP address. If
they do, it routes the message to the local recipient rather than an external domain.
This is a feature, not a bug, and it is the way Exchange has been since Exchange 4.0 days.
Sometimes, observed, real-world behavior is better than any KB article. :-) I suggest you pass along this information for them to read:
http://mscerts.programming4.us/application_server/exchange%20transport%20server%20architecture%20%28part%201%29.aspx
http://technet.microsoft.com/en-us/library/bb232045%28v=exchg.141%29.aspx
http://technet.microsoft.com/en-us/library/bb232193%28v=exchg.141%29.aspx
http://www.msexchange.org/articles-tutorials/exchange-server-2010/planning-architecture/smtp-routing-exchange-2010-part1.html
http://www.msexchange.org/articles-tutorials/exchange-server-2010/planning-architecture/smtp-routing-exchange-2010-part2.html
Jim McBee - MVP, MCT, MCSE Using Exchange since the v4.0 beta in 1995 - Blog http://mostlyexchange.blogspot.com

Gmail Account in iMail - adding multiple exchange SMTP addresses to Gmail

Summary: I am trying to use my Gmail to send messages through iMail from my other addresses that I have added to my Gmail account successfully.
Detail:
I currently have 5 email addresses, and the most recent one I created was my Gmail address. Everything is working perfectly online with gmail and on my ipad - I can send and receive from each email address within my one email account, Gmail, BUT my computer is not happy. I am still willing to work with iMail as I have always enjoyed using it, however it will not allow me to send out emails through my Gmail account using my two email addresses that happen to be Exchange emails. My Pop and IMAP addresses that I have added to my Gmail account are fine and their SMTP addresses are working, but my two Exchange SMTP addresses are currently listed as "Offline" even though I have entered all the information that I think is correct, or is what I entered online in my Gmail account and they work perfectly fine there and also on my ipad. I just can't seem to get them to work in iMail. Everything else is synchronized and everything updates between my iMail, my iPad and the Gmail online account, and I have a feeling that it is just not possible to get the exchange accounts working on the iMail through Gmail. The two emails I am working with here are university emails that have their own addresses, but run through Windows live. So they are smtp.exchangelabs.com, but the actual domains are l.uky.edu and student.gsu.edu. I have been working on this all day so please let me know if you are able to help me in this struggle. I have also downloaded the Gmail notifier, so I will try it out, but I am still a fan of iMail.
Settings in iMail that are currently not working yet are working online with Gmail - in the account preferences under the advanced tab in iMail under the drop menu for SMTP outgoing server where it says "Edit SMTP server list" or something like that:
Server Name: smtp.exchangelabs.com
Advanced:
        Use Custom Port: 587
        SSL is NOT checked (it is TSL for my accounts)
        Authentication: Password
               username: <my entire email address at the domain>@student.gsu.edu
               password: <my password for that email address>

Yeah, this really stinks. The feature is definitely gone in iOS 4. I used it all the time in iPhone OS 3.x. You can still do it in Mail in OS X (the trick is to add extra the email addresses to your main email address, separated by commas. Those will then be available to reply with) but you can't on the iPhone. Even if you tell iTunes to sync your Mail Account info, it doesn't work.
That service seems like an interesting idea but 1) I don't want to send my mail to a third party, 2) I don't want to have to pay for what should be basic functionality, and 3) I shouldn't have to resort to a third-party for what appears to be a regression on Apple's part.

Exchange 2010 add new email address space and additional smtp address to all recipients

HI
Our company is being bought and we need to change the email address for every recipient within the business group/user.
I have added the new domain to the Accepted Domains and have confirmed that if I manually change a users smtp address that mail flow works and the postmaster account receives email.
looking in the E-mail address policies section within the EMC we currently have 2 polices one for the current company policy call company.co.uk with a priority 1 and one called Default policy.
when I try to edit these I get a warning message which states that this policy was created with an earlier version of exchange I have looked on our exchange 2003 environment and have found the polices and can edit them.
Now my questions are
1. should I create the policy on the exchange 2003 environment or 2010
2. if I create a new policy on the exchange 2010 environment what will happen to the old addresses?
3. I must be able to preserve the old addresses and must make the new address space the primary address?
if anyone could help with the steps required or if there are any gotcha to avoid.
thanks

1. should I create the policy on the exchange 2003 environment or 2010
You have to create in Exchange2010
2. if I create a new policy on the exchange 2010 environment what will happen to the old addresses?
Email address policy will change the email address if applied immediately except for the users which has "Automatically update email addresses based on e-mail address policy" option turned on
You will get the list of users with "Automatically update email addresses based on e-mail address policy" option turned off by the below command.
Get-Mailbox -ResultSize Unlimited | Where {$_.EmailAddressPolicyEnabled -eq $False}
3. I must be able to preserve the old addresses and must make the new address space the primary address?
Yes but you can keep only one as replying address.
Please keep both address in the email address policy to preserve old email address to the users.
If you want an autoreply, then use a hub transport rule in Exchange an Outlook rule and allow auto-replies to the internet. (auto-replies to the outside network is not a good idea)
Here is a similar case
http://exchangeserverpro.com/email-address-policies-in-mixed-exchange-20032007-organisations/
Thanks, MAS
Please mark as helpful if you find my comment helpful or as an answer if it does answer your question. That will encourage me - and others - to take time out to help you.

Exchange 2013 - Outlook 2010 - 550 5.1.0 RESOLVER.ADR.InvalidInSmtp; encapsulated INVALID address inside an SMTP address

Hello,
I have issue when sending email to some addresses. Server respond with:
Remote Server returned '550 5.1.0 RESOLVER.ADR.InvalidInSmtp; encapsulated INVALID address inside an SMTP address (IMCEAINVALID-)'
My enviroment: Exchange 2013, Outlook 2010 - no cached mode. Issue happend with two email addresses but not always.
Any suggestion, how to resolve issue?
Thx.

Hi Tomas,
Does this issue occur in OWA? How is the impact, only one user or all users?
Please try to run Outlook under safe mode to avoid add-ins and AVs.
If there is any 3rd party add-ins, please try to disable them for testing.
Thanks
Please remember to mark the replies as answers if they help, and unmark the answers if they provide no help. If you have feedback for TechNet Support, contact [email protected]
Mavis Huang
TechNet Community Support

Exchange - Export only primary SMTP addresses

Hi SpiceHeads,
I'm looking for a script or help to write a script that simply dumps all primary SMTP addresses to a text file, one per line.
Everything I've found or even using exchange powershell includes additional fluff like names or alias's.
Any help would be appreciated.
This topic first appeared in the Spiceworks Community

I'm seeing this same limitation and I'm needing to determine if it is an ActiveSync limitation from Exchange or if it maybe is a limitation of the mobile device.
I have customers who are delegates for multiple exchange mailboxes. For the sake of example I'll use the following:
John Smith ([email protected]) is a delegate on a shared mailbox ([email protected]) and a delegate for his boss, Cheryl Thompson ([email protected]).
John has an Iphone 4S running IOS7. He adds his exchange account ([email protected]) and accesses email/contacts/calendars on that account with no issues.
Next he adds the shared mailbox by putting [email protected] in as the email address of the account, but he uses jsmith with his password as his user credentials. The account is added and John is able to access the shared mailbox and calendars for
this account.
When he trys to add the 3rd account for his boss, he uses his boss' email address ([email protected]) with his jsmith credentials and he gets the following error: "Cannot Create Account: An identical Exchange account already exists."
Any idea of whether this is an Exchange 2010 limitation or an IOS limitation? The infrastructure we are using is Exchange 2010.
Todd Boring
MD Anderson Cancer Center

Exchange SMTP address

Hi,
I have exchange resource configured in my OIM . My requiremnt is whenver user email changes (for any reason .), i have to store the old email address and set the new email address as the primary email address .
Is this provided OOTB ? is there any attribute in exchange which can hold the old email address .
I can see 2 attributes OOTB in exchange connector , 1 is mail and other is mailnickname . mail as i understand is the primay email address , what is this mailnickname for ?
Thanks

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Mail users have spam sent to their secondary SMTP addresses forwarded to their personal e-mail addresses- Exchange 2010

We currently have a spam issue relating to the secondary SMTP e-mail addresses of all our Mail Users.
Example: Peter Smith has an AD account on our company.com domain and an associated external e-mail address ([email protected]) i.e. he has an AD account ([email protected]) with Mail User Exchange attributes so that he can logon
to our SharePoint server. However, this AD account also becomes a fully functional secondary SMTP address and all spam sent to [email protected] also gets forwarded to [email protected]
To mitigate this issue, I have added this secondary e-mail address to the "Recipient filtering properties > Block messages sent to the following recipients" in Hub Transport/Anti Spam.
Two questions:
1. Is there an easy way to delete the secondary SMTP addresses of mail users? I was unable to (it just reappeared shortly after deletion)
2. What is the PS command to export a list of all secondary SMTP e-mail addresses OF MAIL USERS and then adding this list to "Recipient filtering properties > Block messages sent to the following recipients". I could manually add them
in EMC but there are quite a few of them...
Many thanks for your help!

Now that I understand what's happening, let me see if we can get a more accurate solution for you. So your mail users (Exchange calls them mail-enabled users, as opposed to mailbox enabled users, who have mailboxes) have SharePoint access (with the
@company.com address), but have actual mailboxes externally (the actual end-domain is inconsequential). You want users of these systems to stop receiving emails on the company.com namespace, but to receive them from only your SharePoint system.
A "textual diagram" is below:
SharePoint (to Exchange mailbox owner) ==> Exchange hub (using company.com) ==> Exchange mailbox
SharePoint (to External mail user) ==> Exchange hub (using company.com) ==> Exchange mail contact ==> External system (using external SMTP address
External Messaging system (to External mail user, using company.com address used by SharePoint) ==> Exchange hub =XX=> Block delivery
You wish to stop the third of these from happening. If your SharePoint system used non-routable addresses (such as company.local) and all of your mail users had only these addresses added to their accounts for internal mail precossing (as the
internal name used by Exchange), this would solve your issue. The question becomes how to deploy this sort of address.
If these are the ONLY mail contacts in your organization, the solution is simple - you almost had it above, but may have missed seeing it. Policies are applied on a priority basis, with the default policy applying only if no others apply. Since
these accounts are considered "Contacts with external e-mail addresses", you can create a policy for your entire organization that handles only these accounts. You don't need to apply it to a single OU, if your mail enabled accounts aren't
in a single OU. (If they are, of course, feel free to apply it only there.) You can create the policy and apply it to the organization, but only to those objects that are "Contacts with external e-mail addresses". That way, it won't
affect any of your Exchange mailboxes (current or future).
Does this help?
(BTW, one minor correction - your third statement about mail contacts is incorrect - Exchange sees no major difference between mail contacts and mail enabled accounts - and in my experience they are both addressable by the internal address.)

How do we deduce (if we can) SMTP address for an exchange account with only x500 address available? In what cases SMTP address is not available for exchange accounts (please see details below)?

I am using PR_SENDER_EMAIL_ADDRESS to retrieve sender's email address for exchange mails, but for some mails I only get the exchange X500 addresses. In such case, I can use PR_SENDER_ADDRTYPE
to check the type but when I detect an X500 address instead of an SMTP one, is there a way I can enhance SMTP lookup? What might be the reasons that SMTP address is available for some External senders and not for others, as in my case? I am using MAPI CDO
1.2.1 with Exchange Server 2010.
MSDN Question

If you getting an X500 Address that generally means there is Directory object (in Active Directory) for that sender, if its an external sender then it most probably there is an AD Contact from that Sender. The best thing to do is just use resolve method
in CDO to resolve the X500 Address to the Directory object and you should then be able to get the associated SMTP Address from the recipient object. (you also just use LDAP to lookup Active Directory directly).
Cheers
Glen

Exchange Activesync and multiple smtp addresses in same domain

Hi,
Could anyone help with this if it is possible via Exchange Activesync or a third party software?:
I have a domain user called UserA with three smtp addresses in exchange server 2007SP3 (1 primary -
[email protected] ) and 2-secondary -
[email protected] and
[email protected] ).
The user has been successfullly setup on an iphone with Exchange Activesync using the primary address. Now, the management wants UserA to be setup to receive mails for the other two secondary addresses using the Domain username
UserA on the same iphone.
Our Exchange team have tested the practicality of this on the iphone and doesn't seems possible; the error was ''Can't create account- An identical Exchange account already exists''
when this was attempted on iphone. Is this error IOS related or EAS.
I have searched everywhere for any documentations from microsoft or any of the smart phone vendors (please point to any link that may exist) to confirm this as a proof to the management.
Thanks.
Ajagbe T.I.

I'm seeing this same limitation and I'm needing to determine if it is an ActiveSync limitation from Exchange or if it maybe is a limitation of the mobile device.
I have customers who are delegates for multiple exchange mailboxes. For the sake of example I'll use the following:
John Smith ([email protected]) is a delegate on a shared mailbox ([email protected]) and a delegate for his boss, Cheryl Thompson ([email protected]).
John has an Iphone 4S running IOS7. He adds his exchange account ([email protected]) and accesses email/contacts/calendars on that account with no issues.
Next he adds the shared mailbox by putting [email protected] in as the email address of the account, but he uses jsmith with his password as his user credentials. The account is added and John is able to access the shared mailbox and calendars for
this account.
When he trys to add the 3rd account for his boss, he uses his boss' email address ([email protected]) with his jsmith credentials and he gets the following error: "Cannot Create Account: An identical Exchange account already exists."
Any idea of whether this is an Exchange 2010 limitation or an IOS limitation? The infrastructure we are using is Exchange 2010.
Todd Boring
MD Anderson Cancer Center

Adding Custom SMTP address in Bulk Exchange 2010

Hi,
I'm trying to create a script that gets all user mailboxes in Exchange 2010, then adds an additional custom SMTP address (SIP) without removing any existing email address. If I run the script for one user, it works fine (below)
This works for an individual user:
$SIPUsers = Get-Mailbox -Identity user
ForEach ($user in $SIPUsers)
    $SIPUsers.EmailAddresses += "SIP:" + $user.SamAccountName + "@domain.org"
    Set-Mailbox -Identity $user -EmailAddresses $SIPUsers.EmailAddresses
When I run this script (below), it removes all SMTP address, x500, custom secondary alias etc and applies the default email policy. I do get an error as well, which is:
$SIPUsers = Get-Mailbox -RecipientTypeDetails UserMailbox -ResultSize unlimited
ForEach ($user in $SIPUsers)
    $SIPUsers.EmailAddresses += 'SIP:' + $user.SamAccountName +
'@ynhh.sso.ynhh.org'
    Set-Mailbox -Identity $user -EmailAddresses $SIPUsers.EmailAddresses
Error:
Property 'EmailAddresses' cannot be found on this object; make sure it exists and is settable.
At C:\Scripts\SIPAdd.ps1:5 char:15
+     $SIPUsers. <<<< EmailAddresses += "SIP:" + $user.SamAccountName + "@ynhh.sso.ynhh.org"
    + CategoryInfo          : InvalidOperation: (:) [], RuntimeException
    + FullyQualifiedErrorId : PropertyAssignmentException

Actually.. just noticed in your script:
Once you go for the bulk change, you are still trying to call EmailAddresses from $SIPUsers (An array at this point) instead of $User.EmailAddresses.
$SIPUsers = Get-Mailbox -RecipientTypeDetails UserMailbox -ResultSize unlimited
ForEach ($user in $SIPUsers)
$user.EmailAddresses += 'SIP:' + $user.SamAccountName + '@ynhh.sso.ynhh.org'
Set-Mailbox -Identity $user -EmailAddresses $user.EmailAddresses

Will Exchange ever support sending mail from a secondary smtp address?

Most here probably know this but a quick recap:
User has PrimarySMTP address of [email protected] and secondary SMTP of
[email protected] In Outlook, if you set the secondary SMTP address in the "From" field, Exchange will throw an "undeliverable" error stating you're not authorized to send mail as
this user. I know there's
3rd party tools that can help you with this, and ways to circumvent this (using extra accounts or distrigroups) but it's actually really annoying. I've been involved with a lot of companies with different brands (and a domain for each brand) and
who want to communicate with the outside world using these different brandnames. One salesmanager could be involved with different brands and right now you'll have to create a new account or group for each and every brand/domainname.
With every new Exchange one of the first things I check if this behaviour has changed.. Will this ever be implemented? Is there anyone here that could shed some light on that? Is there a reason why this does not change?
Kind regards,
Remco Roxs

Nobody who participates in these forums knows what the future holds at Microsoft. If we did, we wouldn't be able to share it with you in any case because we'd be sworn to secrecy.
Just buy this for your sales manager: http://www.ivasoft.biz/choosefrom2007.shtml
Or just tell him to use two mailboxes.
Ed Crowley MVP "There are seldom good technological solutions to behavioral problems."

Exchange 2003 SMTP resolves to incorrect MX record for Outbound emails

Starting October 2007, we have encountered numerous incidents where users complaint that they can not send emails to randomly with Relayed Denied error.
First we thought the problem is with the receipient servers, but after reviewing the SMTP log intensively, I have noticed that the SMTP service on Exchange Server 2003 SP2 tries to send out emails to wrong IP Addresses (instead of sending out to listed IP of MX record, it tries to send to primary domain IP address).
To test further, we have changed the DNS server of the Exchange Server to public DNS service provided by the ISPs and still received same result.
If the user tries to send the email again (from the bounced back message), it some times goes through.
Has anyone know what the problem is?
Have checked the server configuration, DNS configuration, ran all updates, and yet still same result. Is one of the Microsoft Updates causing this issue?

Here is the official explanation i got from MS, sounds like it is doing what they expect it to do.
Problem Description
When Exchange 2003 sends e-mail to the Internet using DNS to resolve external domain names a DNS query is done for the remote domain's MX records. In the event that the initial MX query returns a "server failure", Exchange 2003 will fall back to a DNS A record query. If this query is, in turn, successful and there is an A record for the domain in question that happens to be listening on port 25, Exchange will make a connection to that server. However, if this server does not relay, or accept e-mail for the intended domain a NDR will be generated with a 5.7.1, or
5.5.0 error message.
There are several domains that have A records that point to IP addresses that accept connections on port 25, but do not relay for the same name space:
Eg: Mindspring.com; Earthlink.net
Resolution
Resolve the DNS resolution problems that are causing occasional MX record failures.
Examples:
1. The Exchange server has multiple default gateways set on a multi-homed server.
This is not a recommended configuration and can cause a number of unexpected network problems. If the internal DNS server the internal NIC points to cannot resolve external DNS queries, this problem can occur.
Action: remove the default gateway from one of the NICs.
This doesn’t applies to us, as we don’t use Internal DNS
2. If the Exchange server points to multiple DNS servers on TCP/IP properties, or on the SMTP Virtual Server properties, verify that each of these DNS servers will return MX records properly. If one of the DNS servers does not return DNS records consistently, rectify this problem.
Action: remove this DNS server from the external DNS tab.
Workaround:
Bypass DNS by creating a SMTP connector with address space of <domain.com> and forward to smart host as the IP address the MX/A points to.
Exchange Query Explained
1. If Exchange finds the MX record(s) for a remote domain (through DNS query) it will not fall back to an A record query in the event the MX record (more precisely, the A record the MX record points to) is temporarily not responding on port 25. Instead, Exchange will try another MX record if one exists. If no other MX records exist and none are responding on port 25, the queue will go into a retry state for this remote domain. When that retry state has expired, Exchange will again attempt to resolve MX records for this domain, and so on.
2. Exchange will fall back to an A record query for the remote domain in the event that no MX record can be found. This is not to say that the MX record does not exist - only that when Exchange issued a DNS query for the remote domain the DNS response was "server failure", which basically means no MX was found. So, the MX record may indeed exist, but Exchange simply could not find it through DNS resolution.
3. Exchange then queries the A record and this happens to return a result. If the A record is listening on port 25, but does not accept mail for <domain.com> then we will get the NDR with 550 5.7.1 unable to relay (or some variation of this NDR error code) when Exchange connects and attempts to send the e-mail.
So, the intermittent nature of the problem is caused by a failure to find the MX record and a success in finding A record. This can happen for a variety of reasons, but it boils down to flakey DNS resolution.
For example:
a. A bad DNS server listed as a forwader on the DNS server.
b. A bad DNS server on the TCP/IP properties.
c. A bad DNS server on the SMTP VS (external DNS servers)
d. Multiple default gateways on Exchange (ie. multiple NICs on different networks, each NIC having a default GW)
A netmon on Exchange will show the failed MX lookup and successful A record lookup; however, it may not be conclusive unless the "bad" DNS server is listed in the netmon trace. For example, if Exchange points to internal DNS server(s) for name resolution and these DNS servers service these DNS queries by Exchange, you may need a netmon on the DNS server(s) as well to determine which DNS server/Forwarder/etc is at fault.
Regards,
Shahul Hameed Dasthagir
Support Engineer | Enterprise Communications Support

GW2k3 Exchange connector smtp addressing

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