Outlook Anywhere, Exchange Active Sync and IPSec


  • Hi Folks

    We have a requirement to secure Outlook Anywhere with IPSec using certificate based authentication. Microsoft have produced a whitepaper (Greg Taylor) in this regard but it doesn't contain enough information to easily implement this and what configuration steps you should take if Exchange Active Sync is required to be deployed as well, which it is in our case.

    The document states that Autodiscover should be deployed on a separate non IPsec secured IP address but also states that Exchange Active Sync doesn't support IPSec. I am confused in regard to how this can be configured as the Exchange Active Sync virtual directory would exist beneath the Exchange web site which would be listening on the same IP address as the OA RPC virtual directory and the IPSec connection security rules would contain the Exchange server IP address as one of the IPSec endpoints and therefore IPSec would be utilised thus breaking EAS. 

    The document can be found here:

    Can anyone assist me here and enlighten me to the additional configuration that is obviously required with this solution but is missing from the whitepapers and blogs on the subject or am I just plain missing something?


    Johny A

    • Edited by JohnyAhmed Thursday, October 15, 2015 9:27 PM
    Thursday, October 15, 2015 9:26 PM

All replies

  • Hi,

    I understand you had some questions about exchange active sync.

    Have you seen the following blog ?

    As this forum focuses on some general discussion about Exchange.

    I suggest we can ask a question in Exchange ActiveSync forum for more help:  

    Thank you for your understanding.



    Friday, October 16, 2015 8:46 AM
  • Hi David

    I'd like to thank you for your response but I have seen these blogs and whitepapers, I actually provided the URL to one of them in my original post. 

    Please read my initial question and understand what I am asking before saying that the post should be moved. My questions are not really about Exchange Active Sync its about securing Outlook Amnywhere with IPSec and therefore it is in the correct place -  Secure Messaging, or the best place that I could find for it. 

    Can anyone be of any assistance?



    Friday, October 16, 2015 9:47 AM