Test-FederationTrust Failed to request delegation token

When running the Test-FederationTrust cmdlet on a CAS server running Exchange 2010 SP1 (RU5v1) I get an error saying that there was an issue getting a delegation token.
The actual output is here:
RunspaceId : 93c95e81-7679-4937-8c78-dc29e3bab37a
Id : FederationTrustConfiguration
Type : Success
Message : FederationTrust object in ActiveDirectory is valid.
RunspaceId : 93c95e81-7679-4937-8c78-dc29e3bab37a
Id : FederationMetadata
Type : Success
Message : The federation trust contains the same certificates published by the security token service in its federat
ion metadata.
RunspaceId : 93c95e81-7679-4937-8c78-dc29e3bab37a
Id : StsCertificate
Type : Success
Message : Valid certificate referenced by property TokenIssuerCertificate in the FederationTrust object.
RunspaceId : 93c95e81-7679-4937-8c78-dc29e3bab37a
Id : StsPreviousCertificate
Type : Success
Message : Valid certificate referenced by property TokenIssuerPrevCertificate in the FederationTrust object.
RunspaceId : 93c95e81-7679-4937-8c78-dc29e3bab37a
Id : OrganizationCertificate
Type : Success
Message : Valid certificate referenced by property OrgPrivCertificate in the FederationTrust object.
RunspaceId : 93c95e81-7679-4937-8c78-dc29e3bab37a
Id : TokenRequest
Type : Error
Message : Failed to request delegation token.
I re-ran the cmdlet with the 'verbose' parameter and got the following:
VERBOSE: [12:49:06.110 GMT] Test-FederationTrust : Beginning processing &
VERBOSE: [12:49:06.110 GMT] Test-FederationTrust : Instantiating handler with index 0 for cmdlet extension agent "Admin
Audit Log Agent".
VERBOSE: [12:49:06.110 GMT] Test-FederationTrust : Current ScopeSet is: { Recipient Read Scope: {{, }}, Recipient Write
Scopes: {{, }}, Configuration Read Scope: {{, }}, Configuration Write Scope(s): {{, }, }, Exclusive Recipient
Scope(s): {}, Exclusive Configuration Scope(s): {} }
VERBOSE: Testing Federation Trust
VERBOSE: [12:49:06.110 GMT] Test-FederationTrust : Resolved current organization: .
VERBOSE: [12:49:06.126 GMT] Test-FederationTrust : Searching objects "extest_5580e4a3ff4a4" of type "ADUser" under the
root "$null".
VERBOSE: [12:49:06.126 GMT] Test-FederationTrust : Previous operation run on global catalog server
'server.domain.net'.
VERBOSE: [12:49:06.141 GMT] Test-FederationTrust : Requesting Federation Metadata from
https://nexus.microsoftonline-p.com/FederationMetadata/2006-12/FederationMetadata.xml.
VERBOSE: [12:49:06.704 GMT] Test-FederationTrust : Parsing Federation Metadata:
<fed:FederationMetadata>
<SNIPPED>
</fed:FederationMetadata>
VERBOSE: [12:49:06.704 GMT] Test-FederationTrust : Retrieved Token Issuer Uri from Federation Metadata:
urn:federation:MicrosoftOnline.
VERBOSE: [12:49:06.704 GMT] Test-FederationTrust : Retrieved Token Issuer Certificate from Federation Metadata:
B02FEAAC45742783AA61FC8DB7D0C5E0FF415239.
VERBOSE: [12:49:06.704 GMT] Test-FederationTrust : Retrieved Token Issuer Previous Certificate from Federation
Metadata: 089D50FCF27AE9642BFCD95384FD0BB9C14427A4.
VERBOSE: [12:49:06.704 GMT] Test-FederationTrust : Retrieved Token Issuer End Point from Federation Metadata:
https://login.microsoftonline.com/extSTS.srf.
VERBOSE: [12:49:06.704 GMT] Test-FederationTrust : Retrieved Web Requestor Redirect End Point from Federation Metadata:
https://login.microsoftonline.com/login.srf.
VERBOSE: [12:49:07.423 GMT] Test-FederationTrust : Failed to request delegation token. Reason: <S:Fault
xmlns:S="http://www.w3.org/2003/05/soap-envelope"><S:Code><S:Value>S:Sender</S:Value><S:Subcode><S:Value>wst:InvalidReq
uest</S:Value></S:Subcode></S:Code><S:Reason><S:Text xml:lang="en-US">Invalid
Request</S:Text></S:Reason><S:Detail><psf:error
xmlns:psf="http://schemas.microsoft.com/Passport/SoapServices/SOAPFault"><psf:value>0x80048820</psf:value><psf:internal
error><psf:code>0x80047867</psf:code><psf:text>Server received a SAML token from an unrecognized issuer.
</psf:text></psf:internalerror></psf:error></S:Detail></S:Fault>
Microsoft.Exchange.Net.WSTrust.SoapFaultException: Soap fault exception received.
at Microsoft.Exchange.Net.WSTrust.SoapClient.Invoke(IEnumerable`1 headers, XmlElement bodyContent)
at Microsoft.Exchange.Net.WSTrust.SecurityTokenService.IssueToken(DelegationTokenRequest request)
at Microsoft.Exchange.Management.SystemConfigurationTasks.TestFederationTrust.GetDelegationToken(ADUser user, Uri
target, SecurityTokenService securityTokenService)
RunspaceId : 93c95e81-7679-4937-8c78-dc29e3bab37a
Id : FederationTrustConfiguration
Type : Success
Message : FederationTrust object in ActiveDirectory is valid.
RunspaceId : 93c95e81-7679-4937-8c78-dc29e3bab37a
Id : FederationMetadata
Type : Success
Message : The federation trust contains the same certificates published by the security token service in its federat
ion metadata.
RunspaceId : 93c95e81-7679-4937-8c78-dc29e3bab37a
Id : StsCertificate
Type : Success
Message : Valid certificate referenced by property TokenIssuerCertificate in the FederationTrust object.
RunspaceId : 93c95e81-7679-4937-8c78-dc29e3bab37a
Id : StsPreviousCertificate
Type : Success
Message : Valid certificate referenced by property TokenIssuerPrevCertificate in the FederationTrust object.
RunspaceId : 93c95e81-7679-4937-8c78-dc29e3bab37a
Id : OrganizationCertificate
Type : Success
Message : Valid certificate referenced by property OrgPrivCertificate in the FederationTrust object.
RunspaceId : 93c95e81-7679-4937-8c78-dc29e3bab37a
Id : TokenRequest
Type : Error
Message : Failed to request delegation token.
VERBOSE: [12:49:07.423 GMT] Test-FederationTrust : Admin Audit Log: Entered Handler:OnComplete.
VERBOSE: [12:49:07.423 GMT] Test-FederationTrust : Ending processing &
I have removed/deleted the federation and re-created it several times to no avail.
Any suggestions?
Regards,
Luke 

Hi All,
I have faced the same issue in test-federationtrust, to solve this issue i have  tried mentioned links only. it works for me !!!
Issue Description:
Issue1:
Id         : FederationMetadata
Type       : failed
Issue 2:
Id         : TokenRequest
Type       : Error
Message    : Failed to request delegation token.
http://russburden.wordpress.com/category/microsoft-federation-gateway/
http://vanhybrid.com/2014/01/12/freebusy-in-a-hybrid-environment-fail-and-test-federationtrust-returns-error-failed-to-validate-delegation-token/
http://support.microsoft.com/kb/2555008
http://community.office365.com/en-us/f/158/t/5598.aspx
First of all, we are facing this issue, where Internet connectivity of Exchange Hybrid Server is coming from Webproxy, so need to define Webproxy in Exchange Powershell
First Exchange Powershell will be
Set-ExchangeServer -Identity Exchhub01 -InternetWebProxy
http://10.10.10.10:3120/
Note: Change Exchange Servername and Proxy IP and Port no as per your enviornment.
Second Command will be
Get-FederationTrust | Set-Federationtrust -RefreshMetaData
Third Command Will be
Test-FederationTrust
or
Test-FederationTrust -UserIdentity <OnPremisesMailbox> -verbose
Note: Test-federation trust will show you the status of Federation Certificate, it should be valid, it takes 5-8 hours to become valid from ExpiryThanks
Kirpal Singh

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    3. Please use another administrator account to logon and print again, then check if this issue still exist.
    4. Please open Event Viewer and check if find some relevant events or errors.
    If any update, please feel free to let us know.
    Best regards,
    Justin Gu
    Please remember to mark the replies as answers if they help and unmark them if they provide no help. If you have feedback for TechNet Support, contact [email protected]

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