• When one of our users tries to login to BPOS using the Microsoft  Online Services Sign In app he  always gets this error message: 

    "The client was unable to establish a secure connection with the server. Please try signing in again. If the problem persists, please contact your system administrator."

    and he cannot go further.

    He is a Mac user in a Mac Pro with Mac OS 10.4.11 and Entourage with Microsoft Office 2004 for Mac (fully updated) and the Microsoft Online  Services Sign In app.

    He is the only one so far and it only happens in his Mac (in other Macs we tried the error doesn’t happen).

    My theory is that when the Microsoft Online Services Sign In app was installed the first time something got corrupted. However, removing/reinstalling the app and re-configuring his settings doesn’t work. It seems file(s) are left behind corrupted and removing/reinstalling doesn’t clear(s) them/it. Doing a full hard disk search didn’t find anything either.

    ANY IDEA??? 

    • Moved by Daniel Trautman Thursday, July 22, 2010 3:02 AM (From:Microsoft Online: Exchange Online)
    • Moved by Rick PenningtonModerator Tuesday, July 27, 2010 9:12 PM incorrect forum (From:Microsoft Online: Services Sign In for Windows)
    Tuesday, July 20, 2010 4:51 PM


All replies

  • Most of the time on Windows systems this is caused by the time on the system being off, I would guess it's the same for Mac's. Sometimes the time zone is incorrect or the daylight savings option isn't selected.


    Chad Mosman, MessageOps |
    Tuesday, July 20, 2010 9:04 PM
  • No, that is not the case for this Mac. The clock is on time, and DST is correct.
    Tuesday, July 20, 2010 9:29 PM
  • Adrian,

    Please follow these instructions for checking to see if the correct certificate has been installed on his system:

    1. Start the Mac SSO Client.
    2. Open a Finder window, go to Applications > Utilities, and then start Keychain Access.
    3. Verify that Microsoft Online Services Keychain is listed in the menu on the left.
    4. Under Certificates, verify that Microsoft Online Svcs BPOS CA1 is present

    If the certificate is not there, you will have to do a complete uninstall by following the instructions below:

      If you wish to delete all traces of the client, you must also remove the following files and folders:

    • /usr/library/keychains/Microsoft Online Services.keychain - File gets destroyed when the app logs out.
    •  /usr/library/logs/Microsoft Online Services/
    • /usr/library/preferences


    Tuesday, July 27, 2010 9:07 PM
  • No, that did not work. :-(
    Thursday, July 29, 2010 5:10 AM
  • Hi,

    if you delete all files in the user's Library folder (~/Library/Preferences) regarding the Sign In Tool and MS Entourage (you must really close Entourage before), pls reinstall the Sign In. Now the Sign In works.




    Sunday, August 01, 2010 3:03 PM
  • No, that did not work either. :-(
    Monday, August 02, 2010 5:54 AM
  • Adrian,


    Please open a service request with the Microsoft Online Support team through the support tab of your administration center or by contacting the correct number for your region listed here:

    Friday, August 27, 2010 11:56 PM