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Exchange 2010 Security Certificate issues with HTTP over RPC

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Hi,

I have a customer who is receiving an error when he opens Outlook 2010 when away from the office. It's the 'There is a problem with the proxy server's security certificate. The name on the security certificate is invalid or does not match the name on the target site ....'

This is only a problem if the 'Only connect to the proxy servers that have this principle name in their certificate:' is checked.

One thing I thought could be the issue is that there are 2 certificates in Exchange, one for some Shoretel phone services. Anyway, here's some more info: 

If anyone can see why I'd be getting this error, please let me know.

[PS] C:\Windows\system32>Get-ExchangeCertificate |fl


AccessRules        : {System.Security.AccessControl.CryptoKeyAccessRule, System.Security.AccessControl.CryptoKeyAccessR
                     ule, System.Security.AccessControl.CryptoKeyAccessRule}
CertificateDomains : {shoretel.dropdesigns.com}
HasPrivateKey      : True
IsSelfSigned       : True
Issuer             : CN=shoretel.dropdesigns.com
NotAfter           : 8/18/2017 7:49:22 AM
NotBefore          : 8/18/2012 7:49:22 AM
PublicKeySize      : 1024
RootCAType         : Registry
SerialNumber       : 14F55404BEA4A69A4EF8544B388B1332
Services           : None
Status             : Valid
Subject            : CN=shoretel.dropdesigns.com
Thumbprint         : 9851E1E48F329B070CFED3CD51EE7612A4354660

AccessRules        : {System.Security.AccessControl.CryptoKeyAccessRule, System.Security.AccessControl.CryptoKeyAccessR
                     ule, System.Security.AccessControl.CryptoKeyAccessRule}
CertificateDomains : {mail.dropdesigns.com}
HasPrivateKey      : True
IsSelfSigned       : False
Issuer             : CN=RapidSSL CA, O="GeoTrust, Inc.", C=US
NotAfter           : 5/17/2013 11:29:39 AM
NotBefore          : 5/14/2012 8:00:58 PM
PublicKeySize      : 2048
RootCAType         : ThirdParty
SerialNumber       : 0686E3
Services           : IMAP, POP, IIS, SMTP
Status             : Valid
Subject            : CN=mail.dropdesigns.com, OU=Domain Control Validated - RapidSSL(R), OU=See www.rapidssl.com/resour
                     ces/cps (c)12, OU=GT00400290, SERIALNUMBER=SkPjj8tYjSwxVX6hbqpF0qO/sVW6oTzO
Thumbprint         : 58586E4897E558CBA26F8398025BD50694FC0134



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