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    Question Outlook Anywhere

    Hello All

    I am having a few issues with Outlook Anywhere with Exchange 2010. I am trying to set this up in a test environment and want to see it working before I migrate this over to our new Exchange 2010 box.
    I have this running on a Dynamic IP as I am testing this at home with my test lab machines.

    I have a 2008 R2 domain Controller, all Woking fine.
    I have a 2008 R2 Server with exchange 2010 install again all working fine, exchange
    sends and receives emails fine so I know that part if fine.

    I have go into the Exchange 2010 console, and enabled the Outlook Anywhere option and it askes for a external URL so i have entered EXCHANGE.MYDOMAIN.CO.UK

    This is all I can setup, here and this completes fine, and I am advised this change can take upto 15 min to take effect.

    30min later, I go to a workstation which is not on the same network, in this case a machine which is connected to the internet via a 3G dongle. I then add the Exchange serverís name, and mailbox name, and under the advance settings tab I enter the URL for exchange anywhere as EXCHANGE.MYDOMAIN.CO.UK

    This then goes away and I guess trys to connect, and after about 30secs comes back and gives me an outlook error saying outlook must be online to be able to complete this task. Outlook is online (I donít mean open as I am making these changes via the Mail icon in the control panel)

    I have also checked this on another internet connection just to make sure the 3G dongle isnít playing up, and still the same error.

    I have opened all the ports on my router that MS say you need, on Reading outlook anywhere works over port 443 (HTTPS)

    The exchange box is running a self-assigned certificate, as itís in a test lab, just thought I would mention this, but I canít see it been an issue?


    Can anyone advise where I could be going wrong?

    Thanks for any advice which can be given as this is driving me nuts.

    IKWeb

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    Quote Originally Posted by IKWeb View Post
    Hello All

    I am having a few issues with Outlook Anywhere with Exchange 2010. I am trying to set this up in a test environment and want to see it working before I migrate this over to our new Exchange 2010 box.
    I have this running on a Dynamic IP as I am testing this at home with my test lab machines.

    I have a 2008 R2 domain Controller, all Woking fine.
    I have a 2008 R2 Server with exchange 2010 install again all working fine, exchange
    sends and receives emails fine so I know that part if fine.

    I have go into the Exchange 2010 console, and enabled the Outlook Anywhere option and it askes for a external URL so i have entered EXCHANGE.MYDOMAIN.CO.UK

    This is all I can setup, here and this completes fine, and I am advised this change can take upto 15 min to take effect.

    30min later, I go to a workstation which is not on the same network, in this case a machine which is connected to the internet via a 3G dongle. I then add the Exchange server’s name, and mailbox name, and under the advance settings tab I enter the URL for exchange anywhere as EXCHANGE.MYDOMAIN.CO.UK

    This then goes away and I guess trys to connect, and after about 30secs comes back and gives me an outlook error saying outlook must be online to be able to complete this task. Outlook is online (I don’t mean open as I am making these changes via the Mail icon in the control panel)

    I have also checked this on another internet connection just to make sure the 3G dongle isn’t playing up, and still the same error.

    I have opened all the ports on my router that MS say you need, on Reading outlook anywhere works over port 443 (HTTPS)

    The exchange box is running a self-assigned certificate, as it’s in a test lab, just thought I would mention this, but I can’t see it been an issue?


    Can anyone advise where I could be going wrong?

    Thanks for any advice which can be given as this is driving me nuts.

    IKWeb
    I've just completed setting this up, whilst I can't specifically help with your case, I can tell you the situations I ran into with mine.

    1) I needed a third party SSL certificate as Outlook Anywhere doesn't work with self signed (or is so hit and miss it's not worth bothering).
    2) Auto Discover. Setting up autodiscover will help you with the "must be online" otherwise you will need to connect the machine to the exchange server first, and then go external. It's a ballache to set up an account externally without autodiscover and a trusted cert.
    3)I ran into the above problems, but the server would check name, ask for credentials and then say couldn't connect was it wasn't online.

    In the end I relented, got autodiscover working perfectly, still couldn't set up from outside the network, so bought a 30 day trial from verisign, tested it worked fine, kept certificate. All is well in the world.

  3. Thanks to deceptivex from:

    IKWeb (25th May 2011)

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    Hi Deceptivex

    Oki, the 1st 2 pointgs you have mentioned, I dont have setup yet, the main reason for this is it was a test enviroment and didnt want to purchased the SSL cert, and also change the DNS settings to much.

    I will now go away, and make these changes and see how far I get. Thanks for your feedback!!

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    No worries mate. My understanding is this;

    1st method is the way I did it, which setting up accounts externally works with Autodiscover on the DNS by simply entering the email and password, and then connects fine through the verisign SSL.

    2nd method is connecting the machine to the domain, setting up outlook. installing the self signed certificate into the trusted root of the machine, going into account settings and entering the HTTP settings. Now when you go off site it should ask for the credentials like normal. I've never got this method working as I couldn't be bothered but if anyone else can shed light a bit more it would be really useful to me as well.

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    Yeah the only issue I have is the machine which will be running outlook anywhere will never be anywhere near the domain let alone attached So looks like the Auto discover is the way to go.

    Just ordered a new HP server. So when that arrives I will install Exchange 2010, no point in going any further with SSL certs etc. on a test machine.

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    I had all sorts of problems with outlook anywhere with exchange 2010..

    thread here in case any of it helps:

    Exchange / Outlook 2010 Autodiscover / Outlook Anywhere [Solved]

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    1. As mentioned you need to make sure Autodiscover is setup. Therefore make sure youre external namespace is setup correctly if using A or SRV records.
    2. When you purchase a cert, make sure you configure it too include all the hostname you require TO INCLUDE autodiscover. Make sure you get this right.
    3. You will have less trouble with a trusted 3rd party SSL cer.
    4. Ensure your firewall is settp to allow traffic thorugh.
    5. You may have a few iisues with IP v6 and and port ranes which you may have to open.
    6. When you deploy, verify your deployment - https://www.testexchangeconnectivity.com/Default.aspx - also help you identify issues with your config.

    Sukh



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