Working with SSL Certificates

Although various methods exist to create and import SSL certificates, this task can be laborious on Windows servers where no certificate policy exists (i.e. standalone servers). This article describes how to manually create and verify a certificate signing requests (CSR) and import the certificate after the CSR has been signed by a certificate authority, using Microsoft's Certreq tool.

Service Providers who already possess certificates and/or manage their certificates with OpenSSL/LibreSSL, find useful information in Importing an Existing Certificate.

Creating or Renewing a Certificate

Follow the below instructions to create or renew a certificate and import it into Windows' certificate store.

Generating a Certificate Signing Request (CSR)

It is assumed that the following steps are carried out on the machine, where the certificate is actually going to be used by MailStore SPE.

• Prepare a text file request.inf with the following content:

;----------------- request.inf -----------------
[Version]
Signature="$Windows NT$"

[NewRequest]
; replace Subject attributes in the line below with real values
Subject = "CN=mailarchive.example.com, OU=Department, O=Organisation, L=Locality, S=State, C=Country"
KeySpec = 1
KeyLength = 2048
Exportable = TRUE
FriendlyName = mailarchive.example.com
MachineKeySet = TRUE
SMIME = False
PrivateKeyArchive = FALSE
UserProtected = FALSE
UseExistingKeySet = FALSE
ProviderName = "Microsoft RSA SChannel Cryptographic Provider"
ProviderType = 12
RequestType = PKCS10
KeyUsage = 0xa0
 
[EnhancedKeyUsageExtension]
OID = 1.3.6.1.5.5.7.3.1 ; this is for Server Authentication

[Extensions]
2.5.29.17 = "{text}"
_continue_ = "DNS=mailarchive.example.com&"
_continue_ = "DNS=archive.example.com&"
_continue_ = "DNS=*.example.com&"

• Adjust the Subject and FriendlyName values according to your needs.
• Adjust the Subject Alternative Names (SAN) in the [Extensions] section as well. Please note that the Common Name (CN) in the Subject is irrelevant for the verification by clients and that all host names must be included as SANs. Additional host names may be added with appending additional _continue_ lines.
• Save the file.
• Open an elevated command prompt and navigate to the directory where the request.inf is stored.
• Create the CSR by executing the following command:

certreq -new request.inf request.csr

Validating the Certificate Signing Request

To verify that the CSR is correct, execute the following command to display it in a human readable format:

certutil -dump request.csr

Submitting the Certificate Signing Request

Submit the CSR to your preferred CA. The CA might ask for the server platform during the submission process. Selecting IIS 7 or None of the listed should be sufficient. After successful approval of the CSR, you will get the signed certificate in return.

Please note: Nowadays most CAs require the installation of intermediate CA certificates. Detailed information about the installation process of intermediate CA certificates is typically included in the electronic delivery of your certificate.

Importing the Certificate

• Open an elevated command prompt and navigate to the directory where the certificate file is stored.
• Execute the following command to import the certificate into the computer's personal certificate store:

certreq -accept certificate.cer

Verifying the Import

• Log on as administrator to the server on which certificate has been imported.
• Open the Microsoft Management Console (MMC)
• Add the Certificate Snap-In by following these steps:
  • Click on File > Add/Remove Snap-In > Certificate > Add >
  • Select Computer Account and click on Next >
  • Select Local Computer and click on Finish
  • Close any open dialog windows
• Click on Certificates (Local Computer) > Personal > Certificates
• Double-click on the previously imported certificate
• Make sure that the private key for the certificate is available.

Repairing the Certificate Store

Sometimes the matching private key cannot be found although the certificate was imported successfully into the correct certificate store. Try to repair the certificate store as follows:

• Open an elevated PowerShell and execute the following command:

Get-ChildItem Cert:\LocalMachine\My | select Subject, Serialnumber, Thumbprint, HasPrivateKey

• Check the subjects, serialnumbers and fingerprints of the installed certificates, to identify the certificate to be used by MailStore.
• Repair the corresponding certificate store by executing the following command, where SerialNumber is the serial number of the certificate that should be used.

certutil -repairstore my SerialNumber

Using the Certificate

• Replace the self-signed certificates in the Client Access Server.

Importing an Existing Certificate

Typically certificates are exchanged between computers by means of Personal Information Exchange (PFX/P12) containers. These can, for example, be created using the export functions of the MMC Snap-In Certificates.

Optional: Creating a PFX Container with OpenSSL/LibreSSL

When the original CSR was not created with Windows' own tools or not even created on a Windows computer, it is unlikely that the private key or the certificate is available in Windows' certificate store of the MailStore SPE computer, but stored on the file system instead.

In this case, a Personal Information Exchange (PFX) container needs to be created first. This container holds the certificate, private key, and all certificates of the certificate chain. After that, the PFX container can by imported into Windows' certificate store.

The following steps need to be executed to convert the certificate files into a PFX container with OpenSSL or LibreSSL:

• Copy the certificate, private key and the certificates of the certificate chain into the OpenSSL or LibreSSL directory.
• Open an elevated command prompt and navigate to this directory.
• Create the PFX container by executing the following command, adjust the file names if necessary:

openssl pkcs12 -export -out certificate.pfx -inkey private_key.key -in certificate.crt -certfile chain_bundle_file.crt

• In some case the created PFX container is not compatible with the Windows system and the import fails with a password error, even when the password is correct. In that case, append the -legacy parameter to the command:

openssl pkcs12 -export -out certificate.pfx -inkey private_key.key -in certificate.crt -certfile chain_bundle_file.crt -legacy

Importing a PFX container

• Open an elevated command prompt and navigate into the directory where the PFX container resides.
• Enter the following command to import the certificate into the personal store of the machine account, adjust the certificate file name if necessary:

certutil -importpfx -enterprise my certificate.pfx

• Enter the password which is used to protect the PFX file.
• Certutil shows a success message when the certificate was imported successfully.

Weblinks

• Microsoft Technet: Certreq
• Microsoft Technet: Certutil
• Microsoft Technet: How to Request a Certificate With a Custom Subject Alternative Name
• LibreSSL
• OpenSSL Documentation