(SQL Server) Duplicate openssl req -newkey rsa:2048 -nodes -keyout mydomain.pem -out mydomain.csr

Demonstrates how to duplicate this OpenSSL command:

openssl req -newkey rsa:2048 -nodes -keyout mydomain.pem -out mydomain.csr

This command creates 2 files:

1. mydomain.csr: this is the file to send to DigiCert or Let's Encrypt (or any other CA)
2. mydomain.pem: this is the private key of the domain.

The second file is needed to pair with the certificate that will later be received from the CA.

Chilkat ActiveX Downloads ActiveX for 32-bit and 64-bit Windows

-- Important: See this note about string length limitations for strings returned by sp_OAMethod calls.
--
CREATE PROCEDURE ChilkatSample
AS
BEGIN
    DECLARE @hr int
    -- Important: Do not use nvarchar(max).  See the warning about using nvarchar(max).
    DECLARE @sTmp0 nvarchar(4000)
    -- This example requires the Chilkat API to have been previously unlocked.
    -- See Global Unlock Sample for sample code.

    DECLARE @rsa int
    -- Use "Chilkat_9_5_0.Rsa" for versions of Chilkat < 10.0.0
    EXEC @hr = sp_OACreate 'Chilkat.Rsa', @rsa OUT
    IF @hr <> 0
    BEGIN
        PRINT 'Failed to create ActiveX component'
        RETURN
    END

    -- Generate a 2048-bit key.  Chilkat RSA supports
    -- key sizes ranging from 512 bits to 8192 bits.
    DECLARE @success int
    EXEC sp_OAMethod @rsa, 'GenerateKey', @success OUT, 2048
    IF @success <> 1
      BEGIN
        EXEC sp_OAGetProperty @rsa, 'LastErrorText', @sTmp0 OUT
        PRINT @sTmp0
        EXEC @hr = sp_OADestroy @rsa
        RETURN
      END

    DECLARE @privKey int
    EXEC sp_OAMethod @rsa, 'ExportPrivateKeyObj', @privKey OUT

    -- Save the private key to unencrypted PKCS8 PEM
    EXEC sp_OAMethod @privKey, 'SavePkcs8PemFile', @success OUT, 'mydomain.pem'

    -- (alternatively) Save the private key to encrypted PKCS8 PEM
    EXEC sp_OAMethod @privKey, 'SavePkcs8EncryptedPemFile', @success OUT, 'myPassword', 'mydomain_enc.pem'

    -- We'll need the private key's modulus for the CSR.
    -- The modulus is not something that needs to be protected.  Most people don't realize
    -- that a public key is actually just a subset of the private key.  The public parts of
    -- an RSA private key are the modulus and exponent.  The exponent is always 65537.
    DECLARE @privKeyXml int
    -- Use "Chilkat_9_5_0.Xml" for versions of Chilkat < 10.0.0
    EXEC @hr = sp_OACreate 'Chilkat.Xml', @privKeyXml OUT

    EXEC sp_OAMethod @privKey, 'GetXml', @sTmp0 OUT
    EXEC sp_OAMethod @privKeyXml, 'LoadXml', @success OUT, @sTmp0

    -- Get the modulus in base64 format:
    DECLARE @keyModulus nvarchar(4000)
    EXEC sp_OAMethod @privKeyXml, 'GetChildContent', @keyModulus OUT, 'Modulus'

    -- --------------------------------------------------------------------------------
    -- Now build the CSR using Chilkat's ASN.1 API.
    -- The keyModulus will be embedded within the ASN.1.

    -- A new ASN.1 object is automatically a SEQUENCE.
    -- Given that the CSR's root item is a SEQUENCE, we can use
    -- this as the root of our CSR.
    DECLARE @asnRoot int
    -- Use "Chilkat_9_5_0.Asn" for versions of Chilkat < 10.0.0
    EXEC @hr = sp_OACreate 'Chilkat.Asn', @asnRoot OUT

    -- Beneath the root, we have a SEQUENCE (the certificate request info), 
    -- another SEQUENCE (the algorithm identifier), and a BITSTRING (the signature data)

    EXEC sp_OAMethod @asnRoot, 'AppendSequence', @success OUT
    EXEC sp_OAMethod @asnRoot, 'AppendSequence', @success OUT

    -- ----------------------------------
    -- Build the Certificate Request Info
    -- ----------------------------------
    DECLARE @asnCertReqInfo int
    EXEC sp_OAMethod @asnRoot, 'GetSubItem', @asnCertReqInfo OUT, 0
    EXEC sp_OAMethod @asnCertReqInfo, 'AppendInt', @success OUT, 0

    -- Build the Subject part of the Certificate Request Info
    DECLARE @asnCertSubject int
    EXEC sp_OAMethod @asnCertReqInfo, 'AppendSequenceR', @asnCertSubject OUT

    -- Add each subject part..
    DECLARE @asnTemp int
    EXEC sp_OAMethod @asnCertSubject, 'AppendSetR', @asnTemp OUT
    EXEC sp_OAMethod @asnTemp, 'AppendSequence2', @success OUT
    -- AppendSequence2 updates the internal reference to the newly appended SEQUENCE.
    -- The OID and printable string are added to the SEQUENCE.
    EXEC sp_OAMethod @asnTemp, 'AppendOid', @success OUT, '2.5.4.6'
    EXEC sp_OAMethod @asnTemp, 'AppendString', @success OUT, 'printable', 'US'
    EXEC @hr = sp_OADestroy @asnTemp

    EXEC sp_OAMethod @asnCertSubject, 'AppendSetR', @asnTemp OUT
    EXEC sp_OAMethod @asnTemp, 'AppendSequence2', @success OUT
    EXEC sp_OAMethod @asnTemp, 'AppendOid', @success OUT, '2.5.4.8'
    EXEC sp_OAMethod @asnTemp, 'AppendString', @success OUT, 'utf8', 'Utah'
    EXEC @hr = sp_OADestroy @asnTemp

    EXEC sp_OAMethod @asnCertSubject, 'AppendSetR', @asnTemp OUT
    EXEC sp_OAMethod @asnTemp, 'AppendSequence2', @success OUT
    EXEC sp_OAMethod @asnTemp, 'AppendOid', @success OUT, '2.5.4.7'
    EXEC sp_OAMethod @asnTemp, 'AppendString', @success OUT, 'utf8', 'Lindon'
    EXEC @hr = sp_OADestroy @asnTemp

    EXEC sp_OAMethod @asnCertSubject, 'AppendSetR', @asnTemp OUT
    EXEC sp_OAMethod @asnTemp, 'AppendSequence2', @success OUT
    EXEC sp_OAMethod @asnTemp, 'AppendOid', @success OUT, '2.5.4.10'
    EXEC sp_OAMethod @asnTemp, 'AppendString', @success OUT, 'utf8', 'DigiCert Inc.'
    EXEC @hr = sp_OADestroy @asnTemp

    EXEC sp_OAMethod @asnCertSubject, 'AppendSetR', @asnTemp OUT
    EXEC sp_OAMethod @asnTemp, 'AppendSequence2', @success OUT
    EXEC sp_OAMethod @asnTemp, 'AppendOid', @success OUT, '2.5.4.11'
    EXEC sp_OAMethod @asnTemp, 'AppendString', @success OUT, 'utf8', 'DigiCert'
    EXEC @hr = sp_OADestroy @asnTemp

    EXEC sp_OAMethod @asnCertSubject, 'AppendSetR', @asnTemp OUT
    EXEC sp_OAMethod @asnTemp, 'AppendSequence2', @success OUT
    EXEC sp_OAMethod @asnTemp, 'AppendOid', @success OUT, '2.5.4.3'
    EXEC sp_OAMethod @asnTemp, 'AppendString', @success OUT, 'utf8', 'example.digicert.com'
    EXEC @hr = sp_OADestroy @asnTemp

    EXEC @hr = sp_OADestroy @asnCertSubject

    -- Build the Public Key Info part of the Certificate Request Info
    DECLARE @asnPubKeyInfo int
    EXEC sp_OAMethod @asnCertReqInfo, 'AppendSequenceR', @asnPubKeyInfo OUT

    DECLARE @asnPubKeyAlgId int
    EXEC sp_OAMethod @asnPubKeyInfo, 'AppendSequenceR', @asnPubKeyAlgId OUT
    EXEC sp_OAMethod @asnPubKeyAlgId, 'AppendOid', @success OUT, '1.2.840.113549.1.1.1'
    EXEC sp_OAMethod @asnPubKeyAlgId, 'AppendNull', @success OUT
    EXEC @hr = sp_OADestroy @asnPubKeyAlgId

    -- The public key itself is a BIT STRING, but the bit string is composed of ASN.1
    -- for the RSA public key.  We'll first build the RSA ASN.1 for the public key
    -- (containing the 2048 bit modulus and exponent), and encoded it to DER, and then add
    -- the DER bytes as a BIT STRING (as a sub-item of asnPubKeyInfo)

    -- This is already a SEQUENCE..
    DECLARE @asnRsaKey int
    -- Use "Chilkat_9_5_0.Asn" for versions of Chilkat < 10.0.0
    EXEC @hr = sp_OACreate 'Chilkat.Asn', @asnRsaKey OUT

    -- The RSA modulus is a big integer.
    EXEC sp_OAMethod @asnRsaKey, 'AppendBigInt', @success OUT, @keyModulus, 'base64'
    EXEC sp_OAMethod @asnRsaKey, 'AppendInt', @success OUT, 65537

    DECLARE @rsaKeyDerBase64 nvarchar(4000)
    EXEC sp_OAMethod @asnRsaKey, 'GetEncodedDer', @rsaKeyDerBase64 OUT, 'base64'

    -- Now add the RSA key DER as a BIT STRING.
    EXEC sp_OAMethod @asnPubKeyInfo, 'AppendBits', @success OUT, @rsaKeyDerBase64, 'base64'
    EXEC @hr = sp_OADestroy @asnPubKeyInfo

    -- The last part of the certificate request info is an empty context-specific constructed item
    -- with a tag equal to 0.
    EXEC sp_OAMethod @asnCertReqInfo, 'AppendContextConstructed', @success OUT, 0

    -- Get the DER of the asnCertReqInfo.  
    -- This will be signed using the RSA private key.
    DECLARE @bdDer int
    -- Use "Chilkat_9_5_0.BinData" for versions of Chilkat < 10.0.0
    EXEC @hr = sp_OACreate 'Chilkat.BinData', @bdDer OUT

    EXEC sp_OAMethod @asnCertReqInfo, 'WriteBd', @success OUT, @bdDer

    -- Add the signature to the ASN.1
    DECLARE @bdSig int
    -- Use "Chilkat_9_5_0.BinData" for versions of Chilkat < 10.0.0
    EXEC @hr = sp_OACreate 'Chilkat.BinData', @bdSig OUT

    EXEC sp_OAMethod @rsa, 'SignBd', @success OUT, @bdDer, 'SHA1', @bdSig
    EXEC sp_OAMethod @bdSig, 'GetEncoded', @sTmp0 OUT, 'base64'
    EXEC sp_OAMethod @asnRoot, 'AppendBits', @success OUT, @sTmp0, 'base64'

    EXEC @hr = sp_OADestroy @asnCertReqInfo

    -- ----------------------------------
    -- Finally, add the algorithm identifier, which is the 2nd sub-item under the root.
    -- ----------------------------------
    DECLARE @asnAlgId int
    EXEC sp_OAMethod @asnRoot, 'GetSubItem', @asnAlgId OUT, 1
    EXEC sp_OAMethod @asnAlgId, 'AppendOid', @success OUT, '1.2.840.113549.1.1.5'
    EXEC sp_OAMethod @asnAlgId, 'AppendNull', @success OUT
    EXEC @hr = sp_OADestroy @asnAlgId

    -- Write the CSR to a DER encoded binary file:
    EXEC sp_OAMethod @asnRoot, 'WriteBinaryDer', @success OUT, 'qa_output/mydomain.csr'
    IF @success <> 1
      BEGIN
        EXEC sp_OAGetProperty @asnRoot, 'LastErrorText', @sTmp0 OUT
        PRINT @sTmp0
        EXEC @hr = sp_OADestroy @rsa
        EXEC @hr = sp_OADestroy @privKeyXml
        EXEC @hr = sp_OADestroy @asnRoot
        EXEC @hr = sp_OADestroy @asnRsaKey
        EXEC @hr = sp_OADestroy @bdDer
        EXEC @hr = sp_OADestroy @bdSig
        RETURN
      END

    -- It is also possible to get the CSR in base64 format:
    DECLARE @csrBase64 nvarchar(4000)
    EXEC sp_OAMethod @asnRoot, 'GetEncodedDer', @csrBase64 OUT, 'base64'


    PRINT 'Base64 CSR:'

    PRINT @csrBase64

    EXEC @hr = sp_OADestroy @privKey


    EXEC @hr = sp_OADestroy @rsa
    EXEC @hr = sp_OADestroy @privKeyXml
    EXEC @hr = sp_OADestroy @asnRoot
    EXEC @hr = sp_OADestroy @asnRsaKey
    EXEC @hr = sp_OADestroy @bdDer
    EXEC @hr = sp_OADestroy @bdSig


END
GO