Working with SSL Certificates

Generating a CSR and importing the certificate with certreq

  • Log on on the host which runs the Client Access Server.
  • Prepare a text file request.inf with the following content
;----------------- request.inf -----------------
Signature="$Windows NT$"

; replace Subject attributes in the line below with real values
Subject = "CN=hostname, OU=Department, O=Organisation, L=Locality, S=State, C=Country"
KeySpec = 1
KeyLength = 2048
Exportable = TRUE
FriendlyName = hostname
MachineKeySet = TRUE
SMIME = False
PrivateKeyArchive = FALSE
UserProtected = FALSE
UseExistingKeySet = FALSE
ProviderName = "Microsoft RSA SChannel Cryptographic Provider"
ProviderType = 12
RequestType = PKCS10
KeyUsage = 0xa0

OID = ; this is for Server Authentication

[Extensions] = "{text}"
_continue_ = "dns=hostname.local&"
_continue_ = "dns=mailstore&"
  • Adjust the Subject, FriendlyName and Extensions fields according to you infrastructure. Remove the entire [Extensions] section, if you do not need SANs. Save the file.

Hint: When there are any SANs defined, the CN in the Subject field will be ignored by clients, therefore you have to add all possible hostnames to the SAN extensions.

  • Open an elevated command prompt and navigate into the directory where the request.inf is stored.

Creating the CSR

certreq -new request.inf request.csr

Validating the CSR

certutil -dump request.csr


openssl.exe req -in request.csr -text -noout
  • Submit the CSR to your CA. You will get a signed certificate in return.

Importing the certificate

certreq -accept certificate.cer
  • Verify with certlm.msc or mmc that the certificate is imported properly in the hosts Personal store and that a matching private key can be found.
  • Replace the self-signed certificates in the Client Access Server.

Creating a self signed certificate

The makecert.exe utility is included in the SPE's installation directory. It can be used to create self-signed certificate.

makecert.exe -r -pe -n "CN=hostname" -b 01/01/2000 -e 01/01/2036 -eku -ss my -sr localMachine -sky exchange -sp "Microsoft RSA SChannel Cryptographic Provider" -sy 12 -a sha1 -len 2048

Replace hostname with your hostname. The certificate will be stored in the host's personal certificate store and can be used in the Client Access Server configuration.

Converting a PEM file into a PFX container with OpenSSL

When the CSR was created with OpenSSL, the private key is not stored in the hosts private key archive automatically. You have to merge private key, certificate and the certificate chain into one PFX container, and import this container into the host's personal certificate store.

Merging the files

openssl pkcs12 -export -out certificate.pfx -inkey privateKey.key -in certificate.crt -certfile CACert.crt

Importing the certificate

certutil -importpfx certificate.pfx


Microsoft Technet: How to Request a Certificate With a Custom Subject Alternative Name

Microsoft Technet: Certreq

Microsoft Technet: Certutil

Microsoft MSDN: makecert

SSL Shopper CSR Decoder

Symantec CSR Decoder