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Can't sync iPhone with exchange 2010 from outside of LAN

Posted on 2015-02-16
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Last Modified: 2015-03-16
I am in the process of moving from Exchange 2003 to Exchange 2010. I have moved a couple of mailboxes across and got Outlook working ok. I couldn't get my iPhone to sync with Exchange 2010 at first, but got it working by enabling inherited permissions in the User security. Now it works fine when in the office and connected to the LAN via wi-first. However, since I left the office last night I haven't been able to sync. So it seems that it works when it can see Exchange from inside the LAN but not from outside the LAN.
I think there must be a port in the router/modem than I need to redirect. I can probably track that down when I get back to the office this morning, but if I change it to get it working for Exchange 2010, won't that break it for a Exchange 2003?
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Question by:gregmiller4it
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Expert Comment

by:Jelle Dedoyard
ID: 40613009
Which is the servername you are using to connect your iphone? Is this name known on the internet?
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Author Comment

by:gregmiller4it
ID: 40613074
It is the computer name (netbios?) of the Server running Exchange 2010. It was working on Exchange 2003 with just the name of the SBS2003 box. Has this changed in Exchange 2010?
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Expert Comment

by:Gareth Gudger
ID: 40613378
Hey Greg,

Let's start with the ActiveSync test from www.exrca.com. Post the results here. That should give us a good idea of what's going on.

Gareth
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Author Comment

by:gregmiller4it
ID: 40613398
HFailed! Here's the result
RCATestResult.html
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Expert Comment

by:Jelle Dedoyard
ID: 40613712
if you enter the internal name of your server into the server field of your iphone you will only be able to sync with it through the LAN. This is good for testing but you will never get your emails over the internet if you do not have an external DNS name + required open ports in your firewall. Sometimes people set it up so the internal and external name matches but it seems to me you are using an internal name and not an external.

Might be the problem that the external name still points to the old exchange server, if you are indeed using an external name?
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Accepted Solution

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Gareth Gudger earned 500 total points
ID: 40614139
Hey Greg,

Looks like you are missing an autodiscover.yourdomain.com record in your external DNS. Can you create that, point it to your 2010 server and rerun the Autodiscover test instead? Let's get that fixed first. Then moved onto ActiveSync.

Also, you will need to make sure autodiscover is one of the names on your cert and that you have port 443 forwarding on your firewall to 2010.
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Author Comment

by:gregmiller4it
ID: 40615189
Can I do this without breaking active sync for all the other users who are still on Exchange 2003?
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Expert Comment

by:Gareth Gudger
ID: 40615196
Yes. Exchange 2003 does not use Autodiscover, which is why your didn't have the record previously.
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Author Comment

by:gregmiller4it
ID: 40615582
" you have port 443 forwarding on your firewall to 2010"
This fixed it. The port was still pointed to the Exchange 2003 server. I have changed the Port to point to the Exchange 2010 server and it is now working for my mail on Exchange 2010.
I am still waiting to hear if the change has broken if for a Exchange 2003.
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Author Comment

by:gregmiller4it
ID: 40615834
So, it seems that the change has knobbled email access on all the smartphones in the organisation!
This time it seems that it doesn't matter whether they are inside the LAN (via wi-fi) or outside, no email is syncing to any phone (except mine). I haven't moved anyone else's mailbox across to Exchange 2010 yet, only mine.
But I expect that if I redirect port 443 back to Exchange 2003, that all the phones will start to work again.
At least I know how to get it working on 2010 as well.
So I think the plan will be to redirect the port back to the old server, migrate all the mailboxes one night or weekend, and then point the port back to Exchange 2010.
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Expert Comment

by:Gareth Gudger
ID: 40615907
Right. If you want to have a longer period of coexistence you would need to set up legacy records (URLs, certs, DNS and some cmdlets) for your Exchange 2003 box.
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Author Comment

by:gregmiller4it
ID: 40615918
So, do you think it is possible to get both Exchange servers running and fully functional, at the same time?
We do only have a single external IP address on our ADSL connection.
I would prefer to do it gradually, if that was possible. But if it too much drama I will just proceed as above.
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Expert Comment

by:Gareth Gudger
ID: 40615930
Ah ok. No if you only have one IP then it wont be possible. Missed that bit of info.
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Author Closing Comment

by:gregmiller4it
ID: 40669744
So I had to bite the bullet and migrate everyone then redirect port 443 in the firewall to Exchange 2010. All fixed!
Thanks heaps
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