troubleshooting Question

iPhone Exchange account doesn't work when on the Wifi, works on 3G

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Frosty555Flag for Canada asked on
ExchangeWindows Server 2012Windows Networking
6 Comments1 Solution612 ViewsLast Modified:
We have an Exchange server on our network which uses a split-dns environment. That is, we use:

""  -   resolves to the internal IP of the exchange server when on the LAN, and it resolves to the external IP of our router when connecting from the Internet.

It took a bit of work to get the certificate working, but I changed all the internal/external URL settings to get Outlook working both inside the lan, and outside the lan, without complaining about certificate issues.

Now we're facing a problem:

iPhones can't add the Exchange Account when they are on the LAN connected to Wifi. They get an error message about not being able to connect to the server.

If they go onto 3G, they can add the EXchange account fine. AND - when they come back onto the WiFi after adding the account for the first time, mail continues to flow and everything works fine.

It's just the initial set up that doesn't work. Also, autodiscover doesn't work either - the iPhone prompts them for their username and server name when try try to set it up on the WiFi.

Any idea what could be wrong?

Exchange 2013 on Windows Server 2012
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