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Outlook desktop fails to connect to server.

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Our office server is SBS 2003 with ISA 2004. We've migrated all users over to O365. All smartphones and tablets have been setup using autodiscover.

When I try to setup a desktop Outlook 2010 computer the setup comes back with  "An encrypted connection to your secure server is not available" I've tried entering the manual setup to which I get the same error. I've setup my home computer with the same manual entries and Outlook works fine.

Do I need to create a new policy in ISA server to allow secure connections?

I ran Remote Connectivity Analyzer and it returned "Connectivity Test Sucessful" for the autodiscover test.  

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  • I went thru ISA to make sure the ports were open and had to open a couple but I still could not use autodiscovery to setup outlook. At one point in the installation the email server address came back to our exchange server. DNS!! I checked our internal dns server and sure enough there was a forward lookup zone using the same domain that pointed back to the server. With caution I removed the A record. Now everything works fine.

    thanks much for the advice.

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  • Hi Rock42,

     

    I would like to suggest you try below steps to troubleshooting your issue based on your situation:

     

    1. Please configure your ISA server to make sure the ports and Office 365 common URLs are not blocked. Please refer this link for the URLS, Ports, and IP Addresses used by Office 365.
    2. After you allowed the port and URLs, please run Desktop Setup to configure your computer and Outlook client for connecting to Office 365, please click here for more detailed information.
    3. Then try to manually configure the Outlook client by follow the Method 3 mentioned in this article.

     

    If there is any update, please feel free to post here.

     

    Thanks,

    Jolin Qiao

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  • Hi Rock42,

    How are things going?

    If you have any other questions or concerns, please do not hesitate to contact us. It is always our pleasure to assist you.

    Thanks,

    Jolin Qiao

    • Top 75 Contributor
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  • I went thru ISA to make sure the ports were open and had to open a couple but I still could not use autodiscovery to setup outlook. At one point in the installation the email server address came back to our exchange server. DNS!! I checked our internal dns server and sure enough there was a forward lookup zone using the same domain that pointed back to the server. With caution I removed the A record. Now everything works fine.

    thanks much for the advice.

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  • Hi Rock42,

    I am glad to hear that your issue has been resolved and thank you for sharing your expierence about resolving this issue. If you have any other quesitons related to Office 365, please feel free to post here with a new thread, we are happy to assist you.

    Thanks,

    Jolin Qiao

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  • Please Check this article May help

    support.microsoft.com/.../2644437

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