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SBS 2008 outlook anywhere not working

I'm running SBS 2008, RWW and OWA work without any issues including no cert warning after running the cert install generated from SBS 2008. My primary issue is I can not get Outlook Anywhere to work. Outlook 2007 tries to connect to exchange server then goes to disconnected. Outlook 2010 gives me a cert name mismatch error. Another issue that may or may not be related is when I start Outlook while connected to the network I get a Security error  "name on the cert does not match" it's looking for autodiscover.domain.com and the cert SBS created is for remote.domain.com. I have rerun the fix network wizard several times with the same result.
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Cdwalter
Asked:
Cdwalter
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1 Solution
 
jaredr80Commented:
Did you issue the cert through EMC or through the SBS Console?

-Jared
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CdwalterAuthor Commented:
It was generated via the fix network wizard in the SBS console
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jaredr80Commented:
You are not able to create a certificate through the Fix My Network wizard to my knowledge. Is this a 3rd party cert or a self signed? If you are in outlook are you getting cert errors?

-Jared
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CdwalterAuthor Commented:
When you run fix network wizard it creates a cert and an installation package in the public download folder. This is a self signed cert and works for RWW and OWA
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jaredr80Commented:
OK. That does not seem to be what we need. Run this script in Exchange Management Shell and paste what it returns.

Get-ExchangeCertificate |FL


-Jared
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CdwalterAuthor Commented:
AccessRules        : {System.Security.AccessControl.CryptoKeyAccessRule, System.Security.AccessControl.CryptoKeyAccessRule}
CertificateDomains : {ATHOS.castle.local}
HasPrivateKey      : True
IsSelfSigned       : False
Issuer             : CN=castle-ATHOS-CA
NotAfter           : 3/31/2013 3:02:22 PM
NotBefore          : 3/31/2012 3:02:22 PM
PublicKeySize      : 2048
RootCAType         : Registry
SerialNumber       : 19C226A9000100000016
Services           : None
Status             : Valid
Subject            : CN=ATHOS.castle.local
Thumbprint         : 47582E2B0451F1590604FB4373FB8F17D52E19C0

AccessRules        : {System.Security.AccessControl.CryptoKeyAccessRule, System.Security.AccessControl.CryptoKeyAccessRule, System.Security.AccessControl.CryptoKeyAccessRule}
CertificateDomains : {remote.castlecomputing.net, castlecomputing.net, ATHOS.castle.local}
HasPrivateKey      : True
IsSelfSigned       : False
Issuer             : CN=castle-ATHOS-CA
NotAfter           : 3/31/2014 10:58:59 AM
NotBefore          : 3/31/2012 10:58:59 AM
PublicKeySize      : 2048
RootCAType         : Registry
SerialNumber       : 18E34CCA000100000014
Services           : POP, IIS, SMTP
Status             : Valid
Subject            : CN=remote.castlecomputing.net
Thumbprint         : 0FA645E0FDF7B5F9DDAAA7F159A2C1553764D518

AccessRules        : {System.Security.AccessControl.CryptoKeyAccessRule, System.Security.AccessControl.CryptoKeyAccessRule}
CertificateDomains : {castlecomputing.net, smtp.castlecomputing.net, pop3.castlecomputing.net}
HasPrivateKey      : True
IsSelfSigned       : True
Issuer             : CN=castlecomputing.net
NotAfter           : 3/31/2013 10:34:31 AM
NotBefore          : 3/31/2012 10:14:31 AM
PublicKeySize      : 2048
RootCAType         : None
SerialNumber       : 1E0317BCD7BA4F854358D57436A26380
Services           : None
Status             : Valid
Subject            : CN=castlecomputing.net
Thumbprint         : 5F8601909C53A9BD6B162936E736A145B71E83AC

AccessRules        : {System.Security.AccessControl.CryptoKeyAccessRule, System.Security.AccessControl.CryptoKeyAccessRule}
CertificateDomains : {castle-ATHOS-CA}
HasPrivateKey      : True
IsSelfSigned       : True
Issuer             : CN=castle-ATHOS-CA
NotAfter           : 3/31/2017 10:06:14 AM
NotBefore          : 3/31/2012 9:56:15 AM
PublicKeySize      : 2048
RootCAType         : Registry
SerialNumber       : 61BB03976E2E23AC470D12D3F1F9C4A8
Services           : None
Status             : Valid
Subject            : CN=castle-ATHOS-CA
Thumbprint         : F453E5693028FF12E41C7406C492E8D29CA0E92D

AccessRules        : {System.Security.AccessControl.CryptoKeyAccessRule, System.Security.AccessControl.CryptoKeyAccessRule}
CertificateDomains : {castle-ATHOS-CA}
HasPrivateKey      : True
IsSelfSigned       : True
Issuer             : CN=castle-ATHOS-CA
NotAfter           : 9/21/2015 1:59:10 PM
NotBefore          : 9/21/2010 1:49:11 PM
PublicKeySize      : 2048
RootCAType         : Enterprise
SerialNumber       : 661ACF72E706229D43F9B708DDD4F2B9
Services           : None
Status             : Valid
Subject            : CN=castle-ATHOS-CA
Thumbprint         : F1E0445660474643A070B2EB71B8B04CA5285E1E

AccessRules        : {System.Security.AccessControl.CryptoKeyAccessRule, System.Security.AccessControl.CryptoKeyAccessRule}
CertificateDomains : {WMSvc-WIN-ECG5C069HOC}
HasPrivateKey      : True
IsSelfSigned       : True
Issuer             : CN=WMSvc-WIN-ECG5C069HOC
NotAfter           : 9/18/2020 1:31:26 PM
NotBefore          : 9/21/2010 1:31:26 PM
PublicKeySize      : 2048
RootCAType         : Registry
SerialNumber       : 8C68D0749EF97EA348606B8F886931B0
Services           : None
Status             : Valid
Subject            : CN=WMSvc-WIN-ECG5C069HOC
Thumbprint         : 493067AAFAAC1A03B7DB5CCCC3847CAA8676B4CA
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jaredr80Commented:
Thanks. My first suggestion would be to delete your valid-active self signed cert and start from square 1. Until we know for sure-it's always better to be safe that it was added from scratch.

-Jared
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CdwalterAuthor Commented:
I've done that a couple times, delete all references I could find then regenerated it
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CdwalterAuthor Commented:
Completely redid default Web on SBS 2008 corrected the problem including uninstalling RPC and reinstalling
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