S/MIME in Outlook Web App 2013

I have followed the steps on how to enable S/MIME in OWA, I have downloaded and install the controls into IE, I can see the menu options to sign or encrypt, but if I try to sign an email I receive a message stating "No certificate was found. If
you have a smart card-based certificate, insert the card and try again.". My SC is in the reader and I used it to log into webmail, but I am never able to tell it which certificate to choose.
Did I miss something in my server configuration?
I have tried this on Windows 7 and Windows 8.
I have not loaded Outlook onto my computers and played with that yet.
Thanks,
Mike

Thanks for the reply. My domain controller is also the CA server and the user accounts authenticate using smart card based authentication. My templates are configured to publish the certs to AD upon creation. Here is the output of my SMIME
config from the Exchange 2013 server.
[PS] C:\Windows\system32>get-smimeconfig
RunspaceId : 3a520117-e3bb-4d78-a5b1-9ac5711ae79f
OWACheckCRLOnSend : False
OWADLExpansionTimeout : 60000
OWAUseSecondaryProxiesWhenFindingCertificates : True
OWACRLConnectionTimeout : 60000
OWACRLRetrievalTimeout : 10000
OWADisableCRLCheck : False
OWAAlwaysSign : False
OWAAlwaysEncrypt : False
OWAClearSign : True
OWAIncludeCertificateChainWithoutRootCertificate : False
OWAIncludeCertificateChainAndRootCertificate : True
OWAEncryptTemporaryBuffers : True
OWASignedEmailCertificateInclusion : False
OWABCCEncryptedEmailForking : 0
OWAIncludeSMIMECapabilitiesInMessage : True
OWACopyRecipientHeaders : False
OWAOnlyUseSmartCard : True
OWATripleWrapSignedEncryptedMail : True
OWAUseKeyIdentifier : False
OWAEncryptionAlgorithms : 6610
OWASigningAlgorithms : 8004
OWAForceSMIMEClientUpgrade : True
OWASenderCertificateAttributesToDisplay :
OWAAllowUserChoiceOfSigningCertificate : True
SMIMECertificateIssuingCA : {0, 0, 0, 0, 67, 69, 82, 84, 25, 0, 0, 0, 1, 0, 0, 0...}
SMIMECertificatesExpiryDate : 12/29/2015 8:37:03 PM
SMIMEExpiredCertificateThumbprint : B86DE1331ACBE3C2601F922B6C8A7EBE3C7C16D3
AdminDisplayName :
ExchangeVersion : 0.1 (8.0.535.0)
Name : Smime Configuration
DistinguishedName : CN=Smime Configuration,CN=Global
Settings,CN=TestDomain,CN=Microsoft
Exchange,CN=Services,CN=Configuration,DC=domain,DC=com
Identity : Smime Configuration
Guid : 2f8ccb7b-99c0-459e-8247-ae3f27480139
ObjectCategory : domain.com/Configuration/Schema/ms-Exch-Container
ObjectClass : {top, container, msExchContainer}
WhenChanged : 1/20/2015 9:49:11 AM
WhenCreated : 1/8/2015 3:28:17 PM
WhenChangedUTC : 1/20/2015 3:49:11 PM
WhenCreatedUTC : 1/8/2015 9:28:17 PM
OrganizationId :
Id : Smime Configuration
OriginatingServer : caroot.domain.com
IsValid : True
ObjectState : Unchanged

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Using Outlook Web App Web Parts in Exchange Server 2013 - OWA ? Possible?
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Stolen iPad was wiped and erased/synched my exchange calendar. I have recovered some of the calendar entries through the outlook web app, but only entries made in the last 15 or so days. Any ideas on how to recover the rest?

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My ipad was stolen over the weekend and i immediately contacted apple to do a data-wipe.
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S/MIME in Outlook Web App 2013

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