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SBS 2008 outlook anywhere not working

Posted on 2012-04-10
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Last Modified: 2012-08-13
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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Question by:Cdwalter
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by:jaredr80
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Did you issue the cert through EMC or through the SBS Console?

-Jared
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Author Comment

by:Cdwalter
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It was generated via the fix network wizard in the SBS console
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Expert Comment

by:jaredr80
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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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by:Cdwalter
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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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by:jaredr80
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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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by:Cdwalter
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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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Expert Comment

by:jaredr80
Comment Utility
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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Accepted Solution

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Cdwalter earned 0 total points
Comment Utility
I've done that a couple times, delete all references I could find then regenerated it
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Author Closing Comment

by:Cdwalter
Comment Utility
Completely redid default Web on SBS 2008 corrected the problem including uninstalling RPC and reinstalling
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