Exchange 2010 / Outlook 2010 after renewing ssl cert outlook throws errors saying using old certificate

Question

I recently renewed my ssl certificate, but when I did outlook starting throwing me the security alert saying that the certificate is expired and the names do not match.  When I click view certificate it shows my old certificate from like 3 years ago,
so like 2 certificates back.
I went into mmc, and it wasn't there, I looked in IIs and the certificate outlook is referencing is still not there.
my autodiscover and oof isn't working now either.
When i go to look at what exchange powershell is doing it shows the correct information, but that doesn't seem to be making it down to the clients.
[PS] C:\Windows\system32>Get-ExchangeCertificate | fl
AccessRules        : {System.Security.AccessControl.CryptoKeyAccessRule, System.Security.AccessControl.CryptoKeyAccessR
                     ule, System.Security.AccessControl.CryptoKeyAccessRule}
CertificateDomains : {example.org, www.example.org, autodiscover.example.org, examplesv1.example.org, mail.example.org}
HasPrivateKey      : True
IsSelfSigned       : False
Issuer             : CN=Go Daddy Secure Certificate Authority - G2, OU=http://certs.godaddy.com/repository/, O="GoDaddy
                     .com, Inc.", L=Scottsdale, S=Arizona, C=US
NotAfter           : 12/29/2015 7:19:39 AM
NotBefore          : 12/29/2014 7:19:39 AM
PublicKeySize      : 2048
RootCAType         : ThirdParty
SerialNumber       : 46CC4C3A784B17B5
Services           : IMAP, POP, IIS, SMTP
Status             : Valid
Subject            : CN=example.org, OU=Domain Control Validated
Thumbprint         : AD79A6B42835A7F79C8517E9C543661C3072A79C
[PS] C:\Windows\system32>get-exchangecertificate
Thumbprint                                Services   Subject
AD79A6B42835A7F79C8517E9C543661C3072A79C  IP.WS.     CN=example.org, OU=Domain Control Validated
so then i ran
[PS] C:\Windows\system32>Get-ClientAccessServer | fl name,autodiscoverserviceinternaluri
Name                           : exampleSV1
AutoDiscoverServiceInternalUri : https://example.org/Autodiscover/autodiscover.xml
when I use the outlook test email auto configuration it shows that it is trying to connect using that autodiscover url, but it fails, so i'm not sure what is going on.
email is working, user just get that annoying popup every few minutes and oof can't be set up.

Answer 1

Here is the error I get when I run that command...
[PS] C:\Windows\system32>Set-ClientAccessServer -Identity ServerName -AutodiscoverServiceInternalUrl https://mail.example.org/autodiscover/autodiscover.xml
A positional parameter cannot be found that accepts argument '-AutodiscoverServiceInternalUrl'.
    + CategoryInfo          : InvalidArgument: (:) [Set-ClientAccessServer],
ParameterBindingException
    + FullyQualifiedErrorId : PositionalParameterNotFound,Set-ClientAccessServer
Here are the analyzer results...
The Microsoft Connectivity Analyzer is attempting to test Autodiscover for [email protected].
Testing Autodiscover failed.
https://testconnectivity.microsoft.com/Images/Minus.gif
Additional Details
Elapsed Time: 2001 ms.
https://testconnectivity.microsoft.com/Images/Minus.gif
Test Steps
https://testconnectivity.microsoft.com/Images/Error.png
Attempting each method of contacting the Autodiscover service.
The Autodiscover service couldn't be contacted successfully by any method.
https://testconnectivity.microsoft.com/Images/Plus.gif
Additional Details
https://testconnectivity.microsoft.com/Images/Minus.gif
Test Steps
https://testconnectivity.microsoft.com/Images/Error.png
Attempting to test potential Autodiscover URL https://example.org:443/Autodiscover/Autodiscover.xml
Testing of this potential Autodiscover URL failed.
https://testconnectivity.microsoft.com/Images/Plus.gif
Additional Details
https://testconnectivity.microsoft.com/Images/Minus.gif
Test Steps
https://testconnectivity.microsoft.com/Images/Success.png
Attempting to resolve the host name example.org in DNS.
The host name resolved successfully.
https://testconnectivity.microsoft.com/Images/Plus.gif
Additional Details
https://testconnectivity.microsoft.com/Images/Success.png
Testing TCP port 443 on host example.org to ensure it's listening and open.
The port was opened successfully.
https://testconnectivity.microsoft.com/Images/Plus.gif
Additional Details
https://testconnectivity.microsoft.com/Images/SuccessWarn.png
Testing the SSL certificate to make sure it's valid.
The certificate passed all validation requirements.
https://testconnectivity.microsoft.com/Images/Plus.gif
Additional Details
https://testconnectivity.microsoft.com/Images/Minus.gif
Test Steps
https://testconnectivity.microsoft.com/Images/Success.png
The Microsoft Connectivity Analyzer is attempting to obtain the SSL certificate from remote server example.org on port 443.
The Microsoft Connectivity Analyzer successfully obtained the remote SSL certificate.
https://testconnectivity.microsoft.com/Images/Plus.gif
Additional Details
https://testconnectivity.microsoft.com/Images/Success.png
Validating the certificate name.
The certificate name was validated successfully.
https://testconnectivity.microsoft.com/Images/Plus.gif
Additional Details
https://testconnectivity.microsoft.com/Images/SuccessWarn.png
Certificate trust is being validated.
The certificate is trusted and all certificates are present in the chain.
https://testconnectivity.microsoft.com/Images/Plus.gif
Test Steps
https://testconnectivity.microsoft.com/Images/Success.png
Testing the certificate date to confirm the certificate is valid.
Date validation passed. The certificate hasn't expired.
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Additional Details
https://testconnectivity.microsoft.com/Images/Success.png
Checking the IIS configuration for client certificate authentication.
Client certificate authentication wasn't detected.
https://testconnectivity.microsoft.com/Images/Plus.gif
Additional Details
https://testconnectivity.microsoft.com/Images/Error.png
Attempting to send an Autodiscover POST request to potential Autodiscover URLs.
Autodiscover settings weren't obtained when the Autodiscover POST request was sent.
https://testconnectivity.microsoft.com/Images/Plus.gif
Additional Details
https://testconnectivity.microsoft.com/Images/Minus.gif
Test Steps
https://testconnectivity.microsoft.com/Images/Error.png
The Microsoft Connectivity Analyzer is attempting to retrieve an XML Autodiscover response from URL https://example.org:443/Autodiscover/Autodiscover.xml
for user [email protected].
The Microsoft Connectivity Analyzer failed to obtain an Autodiscover XML response.
https://testconnectivity.microsoft.com/Images/Plus.gif
Additional Details
https://testconnectivity.microsoft.com/Images/Error.png
Attempting to test potential Autodiscover URL https://autodiscover.example.org:443/Autodiscover/Autodiscover.xml
Testing of this potential Autodiscover URL failed.
https://testconnectivity.microsoft.com/Images/Plus.gif
Additional Details
https://testconnectivity.microsoft.com/Images/Minus.gif
Test Steps
https://testconnectivity.microsoft.com/Images/Error.png
Attempting to resolve the host name autodiscover.example.org in DNS.
The host name couldn't be resolved.
https://testconnectivity.microsoft.com/Images/GreenRtArrow.jpg Tell me more about this issue and how to resolve it
https://testconnectivity.microsoft.com/Images/Plus.gif
Additional Details
https://testconnectivity.microsoft.com/Images/Error.png
Attempting to contact the Autodiscover service using the HTTP redirect method.
The attempt to contact Autodiscover using the HTTP Redirect method failed.
https://testconnectivity.microsoft.com/Images/Plus.gif
Additional Details
https://testconnectivity.microsoft.com/Images/Minus.gif
Test Steps
https://testconnectivity.microsoft.com/Images/Error.png
Attempting to resolve the host name autodiscover.example.org in DNS.
The host name couldn't be resolved.
https://testconnectivity.microsoft.com/Images/GreenRtArrow.jpg Tell me more about this issue and how to resolve it
https://testconnectivity.microsoft.com/Images/Plus.gif
Additional Details
https://testconnectivity.microsoft.com/Images/Error.png
Attempting to contact the Autodiscover service using the DNS SRV redirect method.
The Microsoft Connectivity Analyzer failed to contact the Autodiscover service using the DNS SRV redirect method.
https://testconnectivity.microsoft.com/Images/Plus.gif
Additional Details
https://testconnectivity.microsoft.com/Images/Minus.gif
Test Steps
https://testconnectivity.microsoft.com/Images/Error.png
Attempting to locate SRV record _autodiscover._tcp.example.org in DNS.
The Autodiscover SRV record wasn't found in DNS.
https://testconnectivity.microsoft.com/Images/GreenRtArrow.jpg Tell me more about this issue and how to resolve it
https://testconnectivity.microsoft.com/Images/Plus.gif
Additional Details