Outlook/Exchange Problem

_Kaiser_

Hey all,

Bit of an unusual one here that maybe someone more knowledgeable than me can answer (I've worked in Support for many years but not an Exchange guru by any stretch of the imagination)

OK here's the situation..

Our company works on a client site, uses their network and domain, and laptops/PCs with their software preload. Everyone has a Domain a/c and Exchange mailbox (2010) and all works well.

Some of the managers however also have email addresses provided by our company which they then connect to through the Outlook client on their laptops. It's added as a 2nd email account

For simplicity lets call our company A and the client B.

Here's where the problems start...

- Sometimes when a user sends an email from their A account to a user with a B address, they get back a delivery error saying that the recipient can't be found... but for some reason the recipient's email address has changed from user1@b.com to user1@a.com??

- This also impacts calendars. When sending an invite from the A calendar to a B user, they'll get the same error back. This is also intermittent.

I've done the usual steps..
- deleted cache addresses
- verified address books don't contain incorrect addresses
- setup a new Outlook profile on the user's laptop
- setup the user on a completely different laptop

.. none of it helps, and it's complicated further by the fact that I don't have direct access to the Domain or Exchange servers of A or B (A - our company - is maintained from another site/domain entirely, and B - the client - obviously wouldn't want someone like me messing around on their network)

Of course the Exchange team for A thinks it's at the user's side (which I think I've disproved by the steps above) and B's IT support isn't going to troubleshoot connectivity to a "foreign" Exchange server (understandably), but of course this all USED to work last year - before my time and before our company A migrated to Exchange 2010 I might add.

Personally my theory is that Outlook is getting confused between 2 Exchange servers and address books on completely separate Domains and this is resulting in all these issues.. I'm guessing it was never intended to work in this configuration and that it did at all was a fluke, but is that then indeed the case?

Has anyone seen anything like this before, or at least am I right with my theory above?

Thanks for any help...

Ctrl Alt Del

Hmmm, confusing !

If that will be my site, I'll get one company' email on Outlook (that has local access maybe) while other company I'll use OWA (Outlook Web Access - over https or vpn).

...or...create two Outlook profiles,one profile for each server and show to your users how to switch !?

Can be due to Active Directory,Autodiscovery on Exchange 2010...basically,without access to server,just keep it KISS (Keep IT Simple Stupid - sweet)

_Kaiser_

Ctrl Alt Del wrote: »

Hmmm, confusing !

If that will be my site, I'll get one company' email on Outlook (that has local access maybe) while other company I'll use OWA (Outlook Web Access - over https or vpn).

...or...create two Outlook profiles,one profile for each server and show to your users how to switch !?

Can be due to Active Directory,Autodiscovery on Exchange 2010...basically,without access to server,just keep it KISS (Keep IT Simple Stupid - sweet)

Oh if I could I would believe me

OWA is setup but doesn't give full client functionality of course so not really a runner as a solution. The separate profile idea could be worth a try but I can't see it as a runner either unfortunately.

Reason I say this is that the main user who's having these issues is the MD of our company (it would have to be right? ) and their PA who accesses the MD's calendar for appointments and so on... and because it "used to work" they naturally don't see why it still doesn't - and because it was before my time, I don't have Domain admin access to either network or Exchange box , I'm somewhat stuck in the middle.

So I'm approaching it more from the angle that I've tried to get it working unsuccessfully and therefore am trying to find out if the 2 Exchange servers with 2 Address books on 2 domains linked through a single Outlook client/profile can actually work, or if it's just not supported in that config - in which case one of the other options mentioned will be all they can take.

ressem

Are you using Outlook 2010?
I guess so as multiple exchange accounts prior to this required multiple profiles.

In which case the ribbon buttons operate on the exchange account that you have selected.

The Ribbon in Outlook 2010 is specific to the account at which you are looking. If you click New E-mail in the ribbon while looking at the Inbox of your second Exchange account, your new message will be sent from your second Exchange account.

_Kaiser_

ressem wrote: »

Are you using Outlook 2010?
I guess so as multiple exchange accounts prior to this required multiple profiles.

In which case the ribbon buttons operate on the exchange account that you have selected.

Yes it's Outlook 2010 but what they are doing is hitting New Mail and then choosing the account to send from (under Options) and only if they're sending from account A to someone on with a B address do problems (intermittently) occur.

The problem seems to be when it hits A's Exchange server - it seems to try to translate user1@b.com (which is the correct address) to user1@a.com for some reason and hence gives a delivery failure as a result... that's why I think the problem lies at the back-end

Ctrl Alt Del

guessing here,without full access to end user desktop...why don't try two Exchange accounts under same profile in Outlook 2010?
Each Exchange email account having a connection to his own Exchange server via local,https,vpn!

CptSternn

I think I know the problem.

It depends on which account they are sending from. The sending account will default to their own domain, so if they are sending as Company A it will search Company A's active directory records and if it's not there it fails. If you are sending to Company B it will only search Company B's records and if it's not there it will fail.

The reason it is interment could be down two a few reasons -

First, it could be using one account to send, but if the network is slow it is switching to another account. It could be something in AD. It could be a list of things.

But what you are seeing I have seen before and it all goes down to the account which you are using to send and where it is homed.

To fix it you need to add aliases in both address books to forward to corresponding addresses on the other side.

For example,

joe.soap@company1.com

Also needs an alias on Company B's AD system:

joe.soap@company1.com (forwards to) joe.soap@company2.com

CptSternn

Also check the domains in the Exchange admin and AD. If it is automatically switching the domain in the email address it is because it thinks it is authoritative for that domain and is trying to resolve it to the default email domain.

Capt'n Midnight

almost certainly a red herring , but ....

but 10 years ago I'd have checked if / what the X.400 settings were on the servers. http://www.msexchange.org/tutorials/X400-Connector-Exchange-Server-2003.html Check what the costs are on the servers in case there is somehow a higher cost routing other than SMTP

also the problem is intermittent, have you notice any patterns ?
and just to confirm there's just one exchange server on each side

testicle

Kaiser2000 wrote: »

ressem wrote: »

Are you using Outlook 2010?
I guess so as multiple exchange accounts prior to this required multiple profiles.

In which case the ribbon buttons operate on the exchange account that you have selected.

Yes it's Outlook 2010 but what they are doing is hitting New Mail and then choosing the account to send from (under Options) and only if they're sending from account A to someone on with a B address do problems (intermittently) occur.

The problem seems to be when it hits A's Exchange server - it seems to try to translate user1@b.com (which is the correct address) to user1@a.com for some reason and hence gives a delivery failure as a result... that's why I think the problem lies at the back-end

What they are doing isn't the right way to do it, and as they are finding out, it doesn't work. They need to click the New Mail from within the mailbox they are sending from if the two mailboxes are in different Exchange organizations as they are.