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Thread: Outlook 2003/2007/2010 won't connect to Exchange 2010 remotely

  1. #1
    Join Date
    Jul 2010
    Posts
    3

    Outlook 2003/2007/2010 won't connect to Exchange 2010 remotely

    I have installed Small Business Server 2011 Standard, after the setup I setup the office computers and 2 of the laptops which have successfully been connecting in and outside the office to exchange.

    Last week I was asked to setup an email address on another laptop which is not at the office. I get the following message:

    "There is a problem with the proxy server's security certificate. The secrurity certificate is not from a trusted certifying authority."

    After I click okay I get this.

    "The connection to Microsoft Exchange is unavailable. Outlook must be online or connected to complete this action."

    I can connect web access mail using my browser.

    Things that have changed in the 2 weeks. Some updates were installed on the server, the secretary has been working the outlook exchange console in the office.

    I spent about 30hours cross referencing settings as per stated on the microsoft website and everything is turned on how they say it should be.

    I don't have a 3rd party certificate only the standard self issued server one, but I could connect before without installing the standard certificate.

    I need help.

  2. #2
    Join Date
    Mar 2010
    Posts
    129

    Re: Outlook 2003/2007/2010 won't connect to Exchange 2010 remotely

    Hello I try to find about your query on internet but I did not get any information regarding to your query. But still I think there maybe issue with your exchange server. Basically your exchange server is not able to connect with your server. So I will suggest you to mail your query to Microsoft tech support they will help you for it. I am trying to find more on it. Once I found it I will post here.

  3. #3
    Join Date
    Jul 2010
    Posts
    3

    Re: Outlook 2003/2007/2010 won't connect to Exchange 2010 remotely

    Quote Originally Posted by Nereus View Post
    Hello I try to find about your query on internet but I did not get any information regarding to your query. But still I think there maybe issue with your exchange server. Basically your exchange server is not able to connect with your server. So I will suggest you to mail your query to Microsoft tech support they will help you for it. I am trying to find more on it. Once I found it I will post here.
    I found two problems.

    1. I logged into SBS 2011 console and re-ran setup internet connection and an error came up saying a port was not open (it didn't say which one). This is odd because I ran the same wizard a few days before without any issues.

    Anyways it said click next to fix issue which is did and then I was able to connect outlook 2010 to exchange server again from outside office.

    2. Outlook 2007 still would not connect, I found this to be because the DNS records on my webhost needed to add an SRV record to port 443 after 2 days of trying to get hold of the web host company support team they said they will add the record as per the link above.

    The next day I tried Outlook 2007 again and still problem (outlook 2010 fine). I really not going to bother ringing host again to check if record added. I have read if I purchase an SSL certificate instead on using the server issued certificate than I will not have any of these problems as the certificate tells outlook where the exchange is or something like that. I have order SSL certificate from Crazydomains for $29AUD for year (i thought was pretty cheap) I am still waiting for it to be issued (was told 48hours).

    I can't believe the Exchange 2010 can't communicate with Outlook 2007 out of the box. Outlook and Exchange you couldn't get two more products that go hand in hand, I could understand if it was Outlook 2000 with 11 year gap. 40% of my customers are still on Outlook 2007 the rest are on 2003 with on a very tiny tiny minority on 2010.

    This has cost me hours and hours of time that I can't bill for tut tut.

    Ps also I found not much help on net ATM for SBS 2011, it is better searching for SBS 2008. SBS 2011 (from what I have read) is SBS 2008 with Exchange 2010.

  4. #4
    Join Date
    May 2008
    Posts
    4,085

    Re: Outlook 2003/2007/2010 won't connect to Exchange 2010 remotely

    I too had similar kind of problem and it turned out to be a password authentication-related issue, resolved it by the following:

    Account Settings>Change>More Settings>Security>Change "Negotiate Authentication" to "Password Authentication(NTLM)".

    Should ask you to re-authenticate your domain credentials, and then you should be in. Hopefully this helps.

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