Microsoft Online Services Client Sign-in Issue

I ran into an interesting error last week. I’ve rarely had issues with computers clocks, but for some inexplicable reason, two of my machines were on the wrong time last week. One of the consequences of this fact was that the Microsoft Online Service (MOS) sign-in tool for BPOS (now called Office 365) failed to work. This is one of my public service announcement posts—hopefully, this will help the next person quickly resolve the problem.

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The error didn’t give me any indication that it was an issue with the clock: “The client was unable to establish a secure connection with the server. Please try signing in again.

The solution was simply to set the computer clock correctly and change the server that I was using for online synchronization.

The full error is below. it was also reproducible on the MOS customer portal web page.

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This issue is discussed on the Microsoft Online: Services Sign In for Windows forums here: http://social.technet.microsoft.com/Forums/en/onlineservicessigninapplication/thread/3a5bd983-935b-4610-8cb4-6e11972cf3ee

Full Error:

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.

The page requires a valid SSL client certificate

Your client certificate has expired or is not yet valid. A Secure Sockets Layer (SSL) client certificate is used for identifying you as a valid user of the resource.


Please try the following:

  • Contact the site administrator to establish client certificate permissions.
  • If you already have a valid client certificate, use your Web browser's security features to ensure that your client certificate is installed properly. (Some Web browsers refer to client certificates as browser or personal certificates.)
  • Change your client certificate and click the Refresh button, if appropriate.

HTTP Error 403.17 - Forbidden: Client certificate has expired or is not yet valid.
Internet Information Services (IIS)


Technical Information (for support personnel)

  • Go to Microsoft Product Support Services and perform a title search for the words HTTP and 403.
  • Open IIS Help, which is accessible in IIS Manager (inetmgr), and search for topics titled About Certificates, and About Custom Error Messages.