Messy Exchange question

[Matt_NZ]

Originally Posted by Pranky

Sorry for some reason I assumed you were in Australia and "the server over there" was referring to NZ.

That being said, what SMTP address are you forwarding to from AU?

If you have the NZ server as an authorative server for the AU domain, it will not be sent through the internet send connector and be delivered to a local mailbox instead.

How are your MX records setup for .com.au and .co.nz? Does the .com.au domain get delivered to the AU server or the NZ one?

That's alright...I guess it's a little abnormal for the NZ side of the business to be the bigger one and the Aus side to be the smaller and ignored business :P

Anyway, I did some investigating and it is only mail internally within NZ where the mail sent to the Aus user is only sent to the NZ mailbox. Which makes sense I guess since the NZ Exchange server will match the address to the mailbox and not bother sending it beyond. I tested this with a Gmail address just to make sure it wasn't something special and yes, mail sent to the Gmail address assigned to the NZ mailbox never left the NZ Exchange server to Gmail.

So, the "solution" works alright for everyone but mail coming from NZ.

Originally Posted by schplade

Don't "fix" the issue with dodgy forwarding, etc. Let the users complain to management that it doesn't work so it gets fixed properly.

If the users/management think it is working with your "fix" they wont bother spending money on the proper solution.

Even if I could give them this, there's still plenty of other issues with this setup that should motivate them to put pressure on management to get things fixed properly. Contacts, Calendars and Sent Mail not syncing are another big issue for them.

Originally Posted by SiTh

lol what a ridiculous fix. You need a third domain to forward to from the NZ server so that you can forward back the other way.

The problem here is you are trying to set up Co-Existence between two exchange organizations, which is fine by itself. However you are attempting to get one user to use a mailbox on each side of the fence. This can not be done because you will end up with an endless loop of forwarders. The mailbox that their phone accesses can not forward back to their primary mailbox, because the primary mailbox forwards to their phone's mailbox... get it? You would need 2 mailboxes per user on one of the servers to get around this issue and that's retarded. Even then they would not be able to reply from the phone.

Oh, I'm well aware it's a horrible fix lol. Everytime they call with a new user to be setup on a phone we make a point of listing all the downfalls of what they're making us do. We don't want to do it but we don't have much of a choice. Ultimately, we want to get them on a hosted Exchange service.

The issue you describe isn't happening, however. The forward is only one way - the mailbox on the Aus server forwards to the NZ mailbox only, so they get a copy of what they have on their phones. There's no forward back from the NZ server.

[SiTh]

Originally Posted by Matt_NZ

Oh, I'm well aware it's a horrible fix lol. Everytime they call with a new user to be setup on a phone we make a point of listing all the downfalls of what they're making us do. We don't want to do it but we don't have much of a choice. Ultimately, we want to get them on a hosted Exchange service.

The issue you describe isn't happening, however. The forward is only one way - the mailbox on the Aus server forwards to the NZ mailbox only, so they get a copy of what they have on their phones. There's no forward back from the NZ server.

Ok here's my understanding of what you described previously:

NZ Server -

1. ActiveSync is working.
2. Auth Domain is company.co.nz.
3. NZ users connect outlook and phones to mailboxes here.
4. AU users connect phones to mailboxes here.
5. AU users primary address is set as user@company.com.au on the mailbox on this server. This is so that if they send from their phone replies will land in their outlook and phone mailboxes.

AU Server

1. ActiveSync does not work.
2. Auth Domain is company.com.au
3. AU users connect their outlook here.
4. AU users have their mail forwarded to their phone mailbox.

If this is accurate, then my description of your issue is on the money.

1. AU users access mailboxes on NZ and AU servers.
2. AU forwards to NZ
3. NZ mailboxes can not mail AU mailboxes because their addresses are local.
4. AU users experience their phones and outlook being out of sync. ie items marked as read on the phone, are unread in outlook. Additionally, sent items are not sync'd at all and neither are folders or calendar items.
5. The reason you can not get a decent a resolution is because AU users are access both resources. And endless forwarding loop would occur otherwise.

That second last item on the list is a killer. You might as well have enabled POP or IMAP on the AU server and saved yourself the hassle of involving the NZ server at all. It would have achieved a better result result. At least the folders would sync

Basically what's happening is you have half set up a co-existence scenario that is commonly used for migration purposes. It's especially prevalent when moving to Office365 / Hosted Exchange type scenarios.

However, the difference in your situation is that instead of migrating a user's mailbox, they are accessing both mailboxes at the same time. This is where your "NZ can't mail AU" users issue is stemming from and will not be resolved until either:
A) AU has their active sync fixed and are back to accessing their own exchange organization only or;
B) Both sets of users are migrated into one exchange organization and only accessing one mailbox.

Anyway, hosted exchange is a good idea. I do it for a living among other things if you're after assistance

Good luck with your issue

[schplade]

It isn't possible to just move all the mailboxes to the NZ server and setup a linked mailbox on the AU side to open them is it?

Are your two domains trusted?

[darkanjel]

There is no clean and cheap way to do it within your current capability. Bottom line is, either justify the cost to fix it or deal with the shortcomings.

You could use MailShadow but it has a minimum 30 seat cost per month.

How many seats are we talking? You might have cash incentives from vendors to get someone to help.

edit: if they insist on continuing down this path, at least use journaling and inbox rules to get a copy of sent items on both servers.

[Matt_NZ]

Originally Posted by SiTh

Ok here's my understanding of what you described previously:

You've got the situation sussed

Once upon a time, the Aus business was part of the NZ domain and their mail was served from the NZ Exchange server (there was no Aus Exchange server at the time, just a DC). However, the link charges from NZ to Aus were proving too expensive so they cut the link and from an IT perspective, separated the two businesses. However, to justify a saving, the budget to separate the two was quite limited and not enough servers were purchased (nor was a Virtualised environment considered) to cover what was available when they were running through NZ, hence the somewhat basic Exchange setup. We suspect there were other future business prospects being considered that was mandating everything be done as cheaply as possible.

Originally Posted by schplade

It isn't possible to just move all the mailboxes to the NZ server and setup a linked mailbox on the AU side to open them is it?

Are your two domains trusted?

No, pretty much think of them as two separate companies. Neither domain knows about each other. Theoretically we could use Outlook Anywhere from the NZ Exchange server and move all Australia's mailboxes back, but that would probably end up being just as messy and slow.

Originally Posted by darkanjel

There is no clean and cheap way to do it within your current capability. Bottom line is, either justify the cost to fix it or deal with the shortcomings.

You could use MailShadow but it has a minimum 30 seat cost per month.

How many seats are we talking? You might have cash incentives from vendors to get someone to help.

edit: if they insist on continuing down this path, at least use journaling and inbox rules to get a copy of sent items on both servers.

We're not prepared to spend money to make this situation work better. If they want to spend money, we'll be telling them to spend it on moving to a hosted Exchange environment to get out of this mess completely

[darkanjel]

Originally Posted by Matt_NZ

We're not prepared to spend money to make this situation work better. If they want to spend money, we'll be telling them to spend it on moving to a hosted Exchange environment to get out of this mess completely

How many seats? As I mentioned, you might have kickbacks available.

[Matt_NZ]

Originally Posted by darkanjel

How many seats? As I mentioned, you might have kickbacks available.

I'd say probably around 30 max.

[darkanjel]

Nothing from Microsoft... If you have a significant spend with Telstra (say $500+/month) you have a small kickback available there - enough to part fund your migration.

[CordlezToaster]

Sounds like a good business case to move to office 365.