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Outlook Anywhere finding the wrong certificate RRS feed

  • Question

  • Hi Everyone,

    Just this week, the one user that uses Outlook Anywhere on Outlook 2007 has started receiving certificate errors.  The odd thing is that it's showing me the SSL cert from the Cisco router.  We have a godaddy cert installed on Exchange and IIS and it's been working fine for over a year just up until now.

    If I use webmail, everything works fine and shows the proper cert.

    What is going on here?


    Friday, May 20, 2011 7:42 PM

Answers

  • She emailed me sunday and let me know that at home she was fine, whether she used the VPN or not, no issues.

    Before she left on Friday though, I checked her laptop and saw that when the Wifi was on, she was being sent out that connection (againt the Wifi is internet only, no internal resources). So she was hitting Outlook Anywhere using the external IP address.  I wouldn't think this should be an issue but she was always getting the Cisco's cert.

    Is it possible that Outlook got confused and was hitting the internal IP and the external IP?

    I told her to make sure she has the Wifi off when she's in the office and this has solved her problem.

    Tuesday, May 24, 2011 1:30 PM

All replies

  • Are you using SSL Offloading for Outlook Anywhere?

    What cert is found testing:

    https://www.testexchangeconnectivity.com/

    Friday, May 20, 2011 7:45 PM
  • No SSL offloading.

    The test runs perfectly without any errors and shows it using the proper certificate.

    Friday, May 20, 2011 7:53 PM
  • Is he going through a VPN or something?

    If he connects from another machine ( Or you do from home for example), does it still show the wrong cert?

     


    Friday, May 20, 2011 7:55 PM
  • No VPN, but I asked if she had gotten this error remotely and she said she hasn't brought her laptop home with her this week.

    I told her to take it with her tonight and run Outlook making sure she's not connected to the VPN and see what happens.  Then she'll try Outlook with the VPN connected.

    I did notice that her laptop was connected to the internal LAN via ethernet AND the Wifi network which connects you to the internet only.  I disconnected her from the WIFI and it works without error.  I'll wait until she's home to see what happens remotely.

    Thanks.



    Friday, May 20, 2011 8:06 PM
  • Hello,

     

    If it is possible, would you please collect the following log files and send to me at: v-simwu@microsoft.com

     

    [Please provide a screenshot of the certificate warning in Outlook]

      

    [Collect AutoConfiguration Status in problematic Outlook]

    ========================================

    1. While Outlook is running, click the CTRL key and then right-click the Outlook icon in the system tray and then select “Test Email Autoconfiguration”.

    2. Confirm that your email address is in the address field, uncheck “Use Guessmart” and “secure Guessmart authentication” boxes. Then click the “Test” button.

    3. Once it runs, please send me a screen shot of the Log tab.

     

    [Certificate configuration information]

    =============================

    On CAS server, open “Exchange Management Shell” and type the cmdlet:

     

    Get-ExchangeCertificate |fl >c:\certlog.txt

    Get-autodiscovervirtualdirectory | fl >c:\auto.txt

    Get-clientaccessserver | fl >c:\cas.txt

     

     

    Thanks,

    Simon

    Monday, May 23, 2011 9:37 AM
  • Intriguing,

    How do you publish OutLook Anywhere to the internet?  ISA 2006, UAG 2010, or a third party device?

    I have had issues in the past with certificates that have been renewed recently.  I would have to perform a procedure involving bindings and IIS server.  My issue was after renewing the certificate and installing on exchange outlook anywhere would see the old experied cerfitcate.

    holmesjrh

    Monday, May 23, 2011 10:00 PM
  • She emailed me sunday and let me know that at home she was fine, whether she used the VPN or not, no issues.

    Before she left on Friday though, I checked her laptop and saw that when the Wifi was on, she was being sent out that connection (againt the Wifi is internet only, no internal resources). So she was hitting Outlook Anywhere using the external IP address.  I wouldn't think this should be an issue but she was always getting the Cisco's cert.

    Is it possible that Outlook got confused and was hitting the internal IP and the external IP?

    I told her to make sure she has the Wifi off when she's in the office and this has solved her problem.

    Tuesday, May 24, 2011 1:30 PM
  • Hello,

     

    I think this may be affected by the settings here:

     

     

    Thanks,

    Simon

    Thursday, May 26, 2011 2:04 AM