Cannot Get Mail The connection to the server failed. iPhone 3G and SBS 2003/Exchange with ActiveSync and Self Signed Certificate.

Posted on 2009-02-20
Last Modified: 2012-05-06
I am having a hard time getting an iPhone 3G to connect to SBS 2003 with ActiveSync.  The phone has passed the validation point and has asked if I wanted to sync with Exchange.  I then proceeded to click on the red button and I get Cannot Get Mail The connection to the server failed. I am not sure as to why the connection to the server would fail since it can connect and validate.

I am using SBS 2003 with service pack 2 for Exchange. I have created a self signed certificate and used Safari to connect to the certsrv on SBS http://domain/cersrv and have installed the certificate. I also connected to OWA through Safari. Everything with OWA is working fine. I can get the phone to pass the validation process but I cannot sync the phone. I have checked to make sure OMA is setup in Exchange.  I also tried to connect to the server without SSL and it still failed.
Question by:TechAK
    LVL 65

    Assisted Solution

    There are so many reasons why this could be failing.
    The SSL certificate is an obviously place to start. You don't need to use Certificate Services to generate your own certificate, the Configure Internet and Email wizard will generate one for you. Although a commercial certificate would be the best option.

    I would suggest running the configure internet and email wizard again to ensure that everything is configured correctly.

    Use a test account to test your server from the MS test site:
    The iPhone is actually a poor device to use to diagnose problems.


    Author Comment

    I used Configure E-mail and Internet Connection Wizard (CEICW) to create the SSL certificate.

    I went to and tested the connection.

    I received a Connectivity Test Failed while attempting an Activesync session
    Here is the error:
    Attempting an Activesync session with server
     Errors were encountered while testing the ActiveSync session
     Test Steps
     Attempting to send OPTIONS command to server
     Testing the OPTIONS command failed. See Additional Details for more info
     Additional Details
     A Web Exception occured because an HTTP 401 - Unauthorized response was received from Unknown

    The error is so generic that it leaves me with hardly anything to go by.

    I performed the resolution from MS KB
    This did nothing

    LVL 65

    Assisted Solution

    Is this SBS 2003 RTM or SBS 2003 R2?
    If it is R2 then you don't need to do what it says in 817379 as that is done by the wizard.
    If ti is RTM then you do need to make the changes, but 817379 as it stands has flaws.

    If you browse to https://server/exchange-oma and you get the forms based login page then the problem exists.


    Accepted Solution

    Not sure what was done to fix the situation but the phone started downloading mail over the weekend. Something helped but I cannot pin point it. Thanks for all your support.

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