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The Bouncy Castle Java APIs for CMS, PKCS, EAC, TSP, CMP, CRMF, OCSP, and certificate generation. This jar contains APIs for JDK 1.5 to JDK 1.8. The APIs can be used in conjunction with a JCE/JCA provider such as the one provided with the Bouncy Castle Cryptography APIs.

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package org.bouncycastle.cms;

import java.security.SecureRandom;

import org.bouncycastle.asn1.ASN1EncodableVector;
import org.bouncycastle.asn1.ASN1ObjectIdentifier;
import org.bouncycastle.asn1.ASN1OctetString;
import org.bouncycastle.asn1.DEROctetString;
import org.bouncycastle.asn1.DERSequence;
import org.bouncycastle.asn1.cms.PasswordRecipientInfo;
import org.bouncycastle.asn1.cms.RecipientInfo;
import org.bouncycastle.asn1.pkcs.PBKDF2Params;
import org.bouncycastle.asn1.pkcs.PKCSObjectIdentifiers;
import org.bouncycastle.asn1.x509.AlgorithmIdentifier;
import org.bouncycastle.operator.GenericKey;
import org.bouncycastle.util.Arrays;

public abstract class PasswordRecipientInfoGenerator
    implements RecipientInfoGenerator
{
    protected char[] password;

    private AlgorithmIdentifier keyDerivationAlgorithm;
    private ASN1ObjectIdentifier kekAlgorithm;
    private SecureRandom random;
    private int schemeID;
    private int keySize;
    private int blockSize;
    private PasswordRecipient.PRF prf;
    private byte[] salt;
    private int iterationCount;

    protected PasswordRecipientInfoGenerator(ASN1ObjectIdentifier kekAlgorithm, char[] password)
    {
        this(kekAlgorithm, password, getKeySize(kekAlgorithm), ((Integer)PasswordRecipientInformation.BLOCKSIZES.get(kekAlgorithm)).intValue());
    }

    protected PasswordRecipientInfoGenerator(ASN1ObjectIdentifier kekAlgorithm, char[] password, int keySize, int blockSize)
    {
        this.password = password;
        this.schemeID = PasswordRecipient.PKCS5_SCHEME2_UTF8;
        this.kekAlgorithm = kekAlgorithm;
        this.keySize = keySize;
        this.blockSize = blockSize;
        this.prf = PasswordRecipient.PRF.HMacSHA1;
        this.iterationCount = 1024;
    }

    private static int getKeySize(ASN1ObjectIdentifier kekAlgorithm)
    {
        Integer size = (Integer)PasswordRecipientInformation.KEYSIZES.get(kekAlgorithm);

        if (size == null)
        {
            throw new IllegalArgumentException("cannot find key size for algorithm: " +  kekAlgorithm);
        }

        return size.intValue();
    }

    public PasswordRecipientInfoGenerator setPasswordConversionScheme(int schemeID)
    {
        this.schemeID = schemeID;

        return this;
    }

    public PasswordRecipientInfoGenerator setPRF(PasswordRecipient.PRF prf)
    {
        this.prf = prf;

        return this;
    }

    public PasswordRecipientInfoGenerator setSaltAndIterationCount(byte[] salt, int iterationCount)
    {
        this.salt = Arrays.clone(salt);
        this.iterationCount = iterationCount;

        return this;
    }

    public PasswordRecipientInfoGenerator setSecureRandom(SecureRandom random)
    {
        this.random = random;

        return this;
    }

    public RecipientInfo generate(GenericKey contentEncryptionKey)
        throws CMSException
    {
        byte[] iv = new byte[blockSize];     /// TODO: set IV size properly!

        if (random == null)
        {
            random = new SecureRandom();
        }
        
        random.nextBytes(iv);

        if (salt == null)
        {
            salt = new byte[20];

            random.nextBytes(salt);
        }

        keyDerivationAlgorithm = new AlgorithmIdentifier(PKCSObjectIdentifiers.id_PBKDF2, new PBKDF2Params(salt, iterationCount, prf.prfAlgID));

        byte[] derivedKey = calculateDerivedKey(schemeID, keyDerivationAlgorithm, keySize);

        AlgorithmIdentifier kekAlgorithmId = new AlgorithmIdentifier(kekAlgorithm, new DEROctetString(iv));

        byte[] encryptedKeyBytes = generateEncryptedBytes(kekAlgorithmId, derivedKey, contentEncryptionKey);

        ASN1OctetString encryptedKey = new DEROctetString(encryptedKeyBytes);

        ASN1EncodableVector v = new ASN1EncodableVector();
        v.add(kekAlgorithm);
        v.add(new DEROctetString(iv));

        AlgorithmIdentifier keyEncryptionAlgorithm = new AlgorithmIdentifier(
            PKCSObjectIdentifiers.id_alg_PWRI_KEK, new DERSequence(v));

        return new RecipientInfo(new PasswordRecipientInfo(keyDerivationAlgorithm,
            keyEncryptionAlgorithm, encryptedKey));
    }

    protected abstract byte[] calculateDerivedKey(int schemeID, AlgorithmIdentifier derivationAlgorithm, int keySize)
        throws CMSException;

    protected abstract byte[] generateEncryptedBytes(AlgorithmIdentifier algorithm, byte[] derivedKey, GenericKey contentEncryptionKey)
        throws CMSException;
}