Exchange 2010 Hybrid Office 365 SSL certificate issue


  • We have an Exchange 2010 Office 365 hybrid setup operating. It has been working for about 4 years now and is fully patched up. All mailboxes are located in Exchange Online. Autodiscover is pointing to our hybrid on premise server as recommended by Microsoft. The SSL certificate on the on premise server was about to expire so we replaced it with a newly purchased one. We removed the old certificate completely from the on premise Exchange and also double checked it was removed from the certificate store. I applied a new certificate which applied fine.

    The problem is that when our Outlook 2016 clients and connecting to the on premise Exchange server they are getting the certificate error. Stating that the certificate has expired. You can press view certificate and it is showing the old, expired certificate that was removed and deleted. I can’t for the life of me work out why this is still occurring and how it is seeing this certificate which has been removed from the EMC and the server’s certificate store.
    Any help appreciated.

    2018年7月11日 上午 06:33


  • Hi MatthewCTM,


    1.Please run Get-ExchangeCertificate | fl cmdlet to verify if the certificate was assigned to services.

    2.Test if you will get certificate warning if you login to OWA

    3.Check the Default web site binding setting if the Https is assigned correct certificate.


    Gavin Gao

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    2018年7月12日 上午 05:48
  • Hi Gavin,

    Thanks for the reply. Yes I have tried those three suggestions that you offered. None of them show the old certificate and that is what is stumping me.
    Running the command show the need certificate, the bindings show the new certificate and the webmail also works fine and shows the new certificate.
    I cant understand this. Very weird.

    This is an Office 365 hybrid setup. Is there anywhere else I need to check?

    2018年7月12日 上午 05:57