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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 1.8 and up. 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.tsp;

import java.io.IOException;
import java.math.BigInteger;

import org.bouncycastle.asn1.ASN1Boolean;
import org.bouncycastle.asn1.ASN1Encodable;
import org.bouncycastle.asn1.ASN1Integer;
import org.bouncycastle.asn1.ASN1ObjectIdentifier;
import org.bouncycastle.asn1.tsp.MessageImprint;
import org.bouncycastle.asn1.tsp.TimeStampReq;
import org.bouncycastle.asn1.x509.AlgorithmIdentifier;
import org.bouncycastle.asn1.x509.Extensions;
import org.bouncycastle.asn1.x509.ExtensionsGenerator;
import org.bouncycastle.operator.DefaultDigestAlgorithmIdentifierFinder;

/**
 * Generator for RFC 3161 Time Stamp Request objects.
 */
public class TimeStampRequestGenerator
{
    private static final DefaultDigestAlgorithmIdentifierFinder dgstAlgFinder = new DefaultDigestAlgorithmIdentifierFinder();

    private ASN1ObjectIdentifier reqPolicy;

    private ASN1Boolean certReq;
    private ExtensionsGenerator extGenerator = new ExtensionsGenerator();

    public TimeStampRequestGenerator()
    {
    }

    /**
     * @deprecated use method taking ASN1ObjectIdentifier
     * @param reqPolicy
     */
    public void setReqPolicy(
        String reqPolicy)
    {
        this.reqPolicy= new ASN1ObjectIdentifier(reqPolicy);
    }

    public void setReqPolicy(
        ASN1ObjectIdentifier reqPolicy)
    {
        this.reqPolicy= reqPolicy;
    }

    public void setCertReq(
        boolean certReq)
    {
        this.certReq = ASN1Boolean.getInstance(certReq);
    }

    /**
     * add a given extension field for the standard extensions tag (tag 3)
     * @throws IOException
     * @deprecated use method taking ASN1ObjectIdentifier
     */
    public void addExtension(
        String          OID,
        boolean         critical,
        ASN1Encodable   value)
        throws IOException
    {
        this.addExtension(OID, critical, value.toASN1Primitive().getEncoded());
    }

    /**
     * add a given extension field for the standard extensions tag
     * The value parameter becomes the contents of the octet string associated
     * with the extension.
     * @deprecated use method taking ASN1ObjectIdentifier
     */
    public void addExtension(
        String          OID,
        boolean         critical,
        byte[]          value)
    {
        extGenerator.addExtension(new ASN1ObjectIdentifier(OID), critical, value);
    }

    /**
     * add a given extension field for the standard extensions tag (tag 3)
     * @throws TSPIOException
     */
    public void addExtension(
        ASN1ObjectIdentifier oid,
        boolean              isCritical,
        ASN1Encodable        value)
        throws TSPIOException
    {
        TSPUtil.addExtension(extGenerator, oid, isCritical, value);
    }

    /**
     * add a given extension field for the standard extensions tag
     * The value parameter becomes the contents of the octet string associated
     * with the extension.
     */
    public void addExtension(
        ASN1ObjectIdentifier oid,
        boolean              isCritical,
        byte[]               value)
    {
        extGenerator.addExtension(oid, isCritical, value);
    }

    /**
     * @deprecated use method taking ANS1ObjectIdentifier
     */
    public TimeStampRequest generate(
        String digestAlgorithm,
        byte[] digest)
    {
        return this.generate(digestAlgorithm, digest, null);
    }

    /**
     * @deprecated use method taking ANS1ObjectIdentifier
     */
    public TimeStampRequest generate(
        String      digestAlgorithmOID,
        byte[]      digest,
        BigInteger  nonce)
    {
        if (digestAlgorithmOID == null)
        {
            throw new IllegalArgumentException("No digest algorithm specified");
        }

        ASN1ObjectIdentifier digestAlgOID = new ASN1ObjectIdentifier(digestAlgorithmOID);

        AlgorithmIdentifier algID = dgstAlgFinder.find(digestAlgOID);
        MessageImprint messageImprint = new MessageImprint(algID, digest);

        Extensions  ext = null;
        
        if (!extGenerator.isEmpty())
        {
            ext = extGenerator.generate();
        }
        
        if (nonce != null)
        {
            return new TimeStampRequest(new TimeStampReq(messageImprint,
                    reqPolicy, new ASN1Integer(nonce), certReq, ext));
        }
        else
        {
            return new TimeStampRequest(new TimeStampReq(messageImprint,
                    reqPolicy, null, certReq, ext));
        }
    }

    public TimeStampRequest generate(ASN1ObjectIdentifier digestAlgorithm, byte[] digest)
    {
        return generate(dgstAlgFinder.find(digestAlgorithm), digest);
    }

    public TimeStampRequest generate(ASN1ObjectIdentifier digestAlgorithm, byte[] digest, BigInteger nonce)
    {
        return generate(dgstAlgFinder.find(digestAlgorithm), digest, nonce);
    }

    public TimeStampRequest generate(
        AlgorithmIdentifier     digestAlgorithmID,
        byte[]                  digest)
    {
        return generate(digestAlgorithmID, digest, null);
    }

    public TimeStampRequest generate(
        AlgorithmIdentifier     digestAlgorithmID,
        byte[]                  digest,
        BigInteger              nonce)
    {
        if (digestAlgorithmID == null)
        {
            throw new IllegalArgumentException("digest algorithm not specified");
        }

        MessageImprint messageImprint = new MessageImprint(digestAlgorithmID, digest);

        Extensions  ext = null;

        if (!extGenerator.isEmpty())
        {
            ext = extGenerator.generate();
        }

        if (nonce != null)
        {
            return new TimeStampRequest(new TimeStampReq(messageImprint,
                    reqPolicy, new ASN1Integer(nonce), certReq, ext));
        }
        else
        {
            return new TimeStampRequest(new TimeStampReq(messageImprint,
                    reqPolicy, null, certReq, ext));
        }
    }
}