Hello,

We have recently deployed some Microsoft Surface Pro 3's in my office.  All of them have Office 2013 Basic and work when in the office.  However, a user is getting an error message on one of them when he uses the Surface Pro while traveling. 

The errror message is:  "There is a problem with the Proxy servers security certificate.  The certificate is not from a trusted certifying authority.  Outlook is not able to connect to the proxy server <server.companyname.com>. (Error Code 8). 

I have Googled and BING'd this all morning and am not making much progress.  Items I have verified. 

1. Date and time are correct on the device
2. User does NOT get this error when he is INSIDE the office.
3. After acknowledging the proxy error, the user receives two security alerts, stating there is a problem with the sites security certificate. 
4. We have a valid certificate from GoDaddy on my Exchange 2010 server. 
5. None of my Windows 7 users are receiving this error. 

Thank you in advance for your time. 

Can you run Get-OutlookProvider and provide the results?

Hinte

Below are the results you requests.  Thank you. 

[PS] D:\temp>Get-OutlookProvider

Name                          Server                        CertPrincipalName             TTL
----                              ------                          -----------------                 ---
EXCH                                                                                                     1
EXPR                                                                                                     1
WEB                                                                                                      1

Hinte

Below are the results you requests.  Thank you. 

[PS] D:\temp>Get-OutlookProvider

Name                          Server                        CertPrincipalName             TTL
----                              ------                          -----------------                 ---
EXCH                                                                                                     1
EXPR                                                                                                     1
WEB                                                                                                      1

Try running:

Set-OutlookProvider Exch msstd:<subjectnameofcert>

Set-OutlookProvider EXPR msstd:<subjectnameofcert>

I have seen issues where Outlook doesn't like this not being populated. 

What is the best way to locate <subjectnameofcert> ? 

I went to my exchange server, went to MMC > Certificates and opened that up for LOCAL COMPUTER.  Went to PERSONAL, then CERTIFICATES.  This is where I can see my cert from GoDaddy.  If I double click the cert and go to the DETAILS tab, I can see the SUBJECT listed with a CN=<companyinfo> and OU=Domain Control Validated. 

Is this the information you were mentioning? 

Look at your cert and look for subject name

So here is what I did.  In Outlook, I went to ACCOUNT SETTINGS > Double Clicked my Account.  In the Change Account dialog box, click on MORE SETTINGS.  Next, click on the CONNECTION tab and click EXCHANGE PROXY SETTINGS.  Here is where I found the correct msstd info to verify.  I pasted this into my syntax as such. 

Set-OutlookProvider exch -certprincipalname msstd:webmail.<whatever>.com. 

Set-OutlookProvider expr -certprincipalname msstd:webmail.<whatever>.com

I am getting some folks to test this and I will make sure to mark your answer correct once we verify its working.  Thanks again for your help! 

• Edited by SatcomXT 12 hours 33 minutes ago Spelling

So here is what I did.  In Outlook, I went to ACCOUNT SETTINGS > Double Clicked my Account.  In the Change Account dialog box, click on MORE SETTINGS.  Next, click on the CONNECTION tab and click EXCHANGE PROXY SETTINGS.  Here is where I found the correct msstd info to verify.  I pasted this into my syntax as such. 

Set-OutlookProvider exch -certprincipalname msstd:webmail.<whatever>.com. 

Set-OutlookProvider expr -certprincipalname msstd:webmail.<whatever>.com

I am getting some folks to test this and I will make sure to mark your answer correct once we verify its working.  Thanks again for your help! 

• Edited by SatcomXT Thursday, April 30, 2015 6:52 PM Spelling

So here is what I did.  In Outlook, I went to ACCOUNT SETTINGS > Double Clicked my Account.  In the Change Account dialog box, click on MORE SETTINGS.  Next, click on the CONNECTION tab and click EXCHANGE PROXY SETTINGS.  Here is where I found the correct msstd info to verify.  I pasted this into my syntax as such. 

Set-OutlookProvider exch -certprincipalname msstd:webmail.<whatever>.com. 

Set-OutlookProvider expr -certprincipalname msstd:webmail.<whatever>.com

I am getting some folks to test this and I will make sure to mark your answer correct once we verify its working.  Thanks again for your help! 

• Edited by SatcomXT Thursday, April 30, 2015 6:52 PM Spelling

Hi,
Any updates about your question?
Basic on the error message, its seems something wrong with Exchange certificate. Please refer to below link to check:
https://support.microsoft.com/en-us/kb/923575?wa=wsignin1.0

If the issue persists, please run below command to ensure the authentication methods:
Get-OutlookAnywhere |FL Identity,*Hostname*,*AuthenticaionMethod*,*RequireSsl*
Also, remove the proxy server in Internet option(Open IE Internet Options, Connections - LAN settings - check mark "Automatically detect settings", and uncheck "Use a proxy server for your LAN").

Thanks