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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 1.4. 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.cert.crmf;

import java.math.BigInteger;
import java.util.ArrayList;
import java.util.Date;
import java.util.Iterator;
import java.util.List;

import org.bouncycastle.asn1.ASN1Encodable;
import org.bouncycastle.asn1.ASN1EncodableVector;
import org.bouncycastle.asn1.ASN1Integer;
import org.bouncycastle.asn1.ASN1Null;
import org.bouncycastle.asn1.ASN1ObjectIdentifier;
import org.bouncycastle.asn1.DERNull;
import org.bouncycastle.asn1.DERSequence;
import org.bouncycastle.asn1.DERTaggedObject;
import org.bouncycastle.asn1.crmf.AttributeTypeAndValue;
import org.bouncycastle.asn1.crmf.CertReqMsg;
import org.bouncycastle.asn1.crmf.CertRequest;
import org.bouncycastle.asn1.crmf.CertTemplate;
import org.bouncycastle.asn1.crmf.CertTemplateBuilder;
import org.bouncycastle.asn1.crmf.OptionalValidity;
import org.bouncycastle.asn1.crmf.PKMACValue;
import org.bouncycastle.asn1.crmf.POPOPrivKey;
import org.bouncycastle.asn1.crmf.ProofOfPossession;
import org.bouncycastle.asn1.crmf.SubsequentMessage;
import org.bouncycastle.asn1.x500.X500Name;
import org.bouncycastle.asn1.x509.ExtensionsGenerator;
import org.bouncycastle.asn1.x509.GeneralName;
import org.bouncycastle.asn1.x509.SubjectPublicKeyInfo;
import org.bouncycastle.asn1.x509.Time;
import org.bouncycastle.cert.CertIOException;
import org.bouncycastle.operator.ContentSigner;

public class CertificateRequestMessageBuilder
{
    private final BigInteger certReqId;

    private ExtensionsGenerator extGenerator;
    private CertTemplateBuilder templateBuilder;
    private List controls;
    private ContentSigner popSigner;
    private PKMACBuilder pkmacBuilder;
    private char[] password;
    private GeneralName sender;
    private int popoType = ProofOfPossession.TYPE_KEY_ENCIPHERMENT;
    private POPOPrivKey popoPrivKey;
    private ASN1Null popRaVerified;
    private PKMACValue agreeMAC;

    public CertificateRequestMessageBuilder(BigInteger certReqId)
    {
        this.certReqId = certReqId;

        this.extGenerator = new ExtensionsGenerator();
        this.templateBuilder = new CertTemplateBuilder();
        this.controls = new ArrayList();
    }

    public CertificateRequestMessageBuilder setPublicKey(SubjectPublicKeyInfo publicKey)
    {
        if (publicKey != null)
        {
            templateBuilder.setPublicKey(publicKey);
        }

        return this;
    }

    public CertificateRequestMessageBuilder setIssuer(X500Name issuer)
    {
        if (issuer != null)
        {
            templateBuilder.setIssuer(issuer);
        }

        return this;
    }

    public CertificateRequestMessageBuilder setSubject(X500Name subject)
    {
        if (subject != null)
        {
            templateBuilder.setSubject(subject);
        }

        return this;
    }

    public CertificateRequestMessageBuilder setSerialNumber(BigInteger serialNumber)
    {
        if (serialNumber != null)
        {
            templateBuilder.setSerialNumber(new ASN1Integer(serialNumber));
        }

        return this;
    }

    /**
     * Request a validity period for the certificate. Either, but not both, of the date parameters may be null.
     *
     * @param notBeforeDate not before date for certificate requested.
     * @param notAfterDate not after date for the certificate requested.
     *
     * @return the current builder.
     */
    public CertificateRequestMessageBuilder setValidity(Date notBeforeDate, Date notAfterDate)
    {
        templateBuilder.setValidity(new OptionalValidity(createTime(notBeforeDate), createTime(notAfterDate)));

        return this;
    }

    private Time createTime(Date date)
    {
        if (date != null)
        {
            return new Time(date);
        }

        return null;
    }

    public CertificateRequestMessageBuilder addExtension(
        ASN1ObjectIdentifier oid,
        boolean              critical,
        ASN1Encodable        value)
        throws CertIOException
    {
        CRMFUtil.addExtension(extGenerator, oid, critical, value);

        return this;
    }

    public CertificateRequestMessageBuilder addExtension(
        ASN1ObjectIdentifier oid,
        boolean              critical,
        byte[]               value)
    {
        extGenerator.addExtension(oid, critical, value);

        return this;
    }

    public CertificateRequestMessageBuilder addControl(Control control)
    {
        controls.add(control);

        return this;
    }

    public CertificateRequestMessageBuilder setProofOfPossessionSigningKeySigner(ContentSigner popSigner)
    {
        if (popoPrivKey != null || popRaVerified != null || agreeMAC != null)
        {
            throw new IllegalStateException("only one proof of possession allowed");
        }

        this.popSigner = popSigner;

        return this;
    }

    public CertificateRequestMessageBuilder setProofOfPossessionSubsequentMessage(SubsequentMessage msg)
    {
        if (popSigner != null || popRaVerified != null || agreeMAC != null)
        {
            throw new IllegalStateException("only one proof of possession allowed");
        }

        this.popoType = ProofOfPossession.TYPE_KEY_ENCIPHERMENT;
        this.popoPrivKey = new POPOPrivKey(msg);

        return this;
    }

    public CertificateRequestMessageBuilder setProofOfPossessionSubsequentMessage(int type, SubsequentMessage msg)
    {
        if (popSigner != null || popRaVerified != null || agreeMAC != null)
        {
            throw new IllegalStateException("only one proof of possession allowed");
        }
        if (type != ProofOfPossession.TYPE_KEY_ENCIPHERMENT && type != ProofOfPossession.TYPE_KEY_AGREEMENT)
        {
            throw new IllegalArgumentException("type must be ProofOfPossession.TYPE_KEY_ENCIPHERMENT || ProofOfPossession.TYPE_KEY_AGREEMENT");
        }

        this.popoType = type;
        this.popoPrivKey = new POPOPrivKey(msg);

        return this;
    }

    public CertificateRequestMessageBuilder setProofOfPossessionAgreeMAC(PKMACValue macValue)
    {
        if (popSigner != null || popRaVerified != null || popoPrivKey != null)
        {
            throw new IllegalStateException("only one proof of possession allowed");
        }

        this.agreeMAC = macValue;

        return this;
    }

    public CertificateRequestMessageBuilder setProofOfPossessionRaVerified()
    {
        if (popSigner != null || popoPrivKey != null)
        {
            throw new IllegalStateException("only one proof of possession allowed");
        }

        this.popRaVerified = DERNull.INSTANCE;

        return this;
    }

    public CertificateRequestMessageBuilder setAuthInfoPKMAC(PKMACBuilder pkmacBuilder, char[] password)
    {
        this.pkmacBuilder = pkmacBuilder;
        this.password = password;

        return this;
    }

    public CertificateRequestMessageBuilder setAuthInfoSender(X500Name sender)
    {
        return setAuthInfoSender(new GeneralName(sender));
    }

    public CertificateRequestMessageBuilder setAuthInfoSender(GeneralName sender)
    {
        this.sender = sender;

        return this;
    }

    public CertificateRequestMessage build()
        throws CRMFException
    {
        ASN1EncodableVector v = new ASN1EncodableVector();

        v.add(new ASN1Integer(certReqId));

        if (!extGenerator.isEmpty())
        {
            templateBuilder.setExtensions(extGenerator.generate());
        }

        v.add(templateBuilder.build());

        if (!controls.isEmpty())
        {
            ASN1EncodableVector controlV = new ASN1EncodableVector();

            for (Iterator it = controls.iterator(); it.hasNext();)
            {
                Control control = (Control)it.next();

                controlV.add(new AttributeTypeAndValue(control.getType(), control.getValue()));
            }

            v.add(new DERSequence(controlV));
        }

        CertRequest request = CertRequest.getInstance(new DERSequence(v));

        v = new ASN1EncodableVector();

        v.add(request);

        if (popSigner != null)
        {
            CertTemplate template = request.getCertTemplate();

            if (template.getSubject() == null || template.getPublicKey() == null)
            {
                SubjectPublicKeyInfo pubKeyInfo = request.getCertTemplate().getPublicKey();
                ProofOfPossessionSigningKeyBuilder builder = new ProofOfPossessionSigningKeyBuilder(pubKeyInfo);

                if (sender != null)
                {
                    builder.setSender(sender);
                }
                else
                {
                    PKMACValueGenerator pkmacGenerator = new PKMACValueGenerator(pkmacBuilder);

                    builder.setPublicKeyMac(pkmacGenerator, password);
                }

                v.add(new ProofOfPossession(builder.build(popSigner)));
            }
            else
            {
                ProofOfPossessionSigningKeyBuilder builder = new ProofOfPossessionSigningKeyBuilder(request);

                v.add(new ProofOfPossession(builder.build(popSigner)));
            }
        }
        else if (popoPrivKey != null)
        {
            v.add(new ProofOfPossession(popoType, popoPrivKey));
        }
        else if (agreeMAC != null)
        {
            v.add(new ProofOfPossession(ProofOfPossession.TYPE_KEY_AGREEMENT,
                    POPOPrivKey.getInstance(new DERTaggedObject(false, POPOPrivKey.agreeMAC, agreeMAC))));

        }
        else if (popRaVerified != null)
        {
            v.add(new ProofOfPossession());
        }

        return new CertificateRequestMessage(CertReqMsg.getInstance(new DERSequence(v)));
    }
}