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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.mime.smime;

import java.io.ByteArrayOutputStream;
import java.io.IOException;
import java.io.OutputStream;
import java.math.BigInteger;
import java.security.SecureRandom;
import java.util.Collections;
import java.util.HashMap;
import java.util.Iterator;
import java.util.LinkedHashMap;
import java.util.List;
import java.util.Map;
import java.util.Set;
import java.util.TreeSet;

import org.bouncycastle.asn1.x509.AlgorithmIdentifier;
import org.bouncycastle.cert.X509CertificateHolder;
import org.bouncycastle.cms.CMSAlgorithm;
import org.bouncycastle.cms.CMSException;
import org.bouncycastle.cms.CMSSignedDataStreamGenerator;
import org.bouncycastle.cms.SignerInfoGenerator;
import org.bouncycastle.mime.Headers;
import org.bouncycastle.mime.MimeWriter;
import org.bouncycastle.mime.encoding.Base64OutputStream;
import org.bouncycastle.util.Store;
import org.bouncycastle.util.Strings;

/**
 * Writer for SMIME Signed objects.
 */
public class SMIMESignedWriter
    extends MimeWriter
{
    public static final Map RFC3851_MICALGS;
    public static final Map RFC5751_MICALGS;
    public static final Map STANDARD_MICALGS;

    static
    {
        Map stdMicAlgs = new HashMap();

        stdMicAlgs.put(CMSAlgorithm.MD5, "md5");
        stdMicAlgs.put(CMSAlgorithm.SHA1, "sha-1");
        stdMicAlgs.put(CMSAlgorithm.SHA224, "sha-224");
        stdMicAlgs.put(CMSAlgorithm.SHA256, "sha-256");
        stdMicAlgs.put(CMSAlgorithm.SHA384, "sha-384");
        stdMicAlgs.put(CMSAlgorithm.SHA512, "sha-512");
        stdMicAlgs.put(CMSAlgorithm.GOST3411, "gostr3411-94");
        stdMicAlgs.put(CMSAlgorithm.GOST3411_2012_256, "gostr3411-2012-256");
        stdMicAlgs.put(CMSAlgorithm.GOST3411_2012_512, "gostr3411-2012-512");

        RFC5751_MICALGS = Collections.unmodifiableMap(stdMicAlgs);

        Map oldMicAlgs = new HashMap();

        oldMicAlgs.put(CMSAlgorithm.MD5, "md5");
        oldMicAlgs.put(CMSAlgorithm.SHA1, "sha1");
        oldMicAlgs.put(CMSAlgorithm.SHA224, "sha224");
        oldMicAlgs.put(CMSAlgorithm.SHA256, "sha256");
        oldMicAlgs.put(CMSAlgorithm.SHA384, "sha384");
        oldMicAlgs.put(CMSAlgorithm.SHA512, "sha512");
        oldMicAlgs.put(CMSAlgorithm.GOST3411, "gostr3411-94");
        oldMicAlgs.put(CMSAlgorithm.GOST3411_2012_256, "gostr3411-2012-256");
        oldMicAlgs.put(CMSAlgorithm.GOST3411_2012_512, "gostr3411-2012-512");

        RFC3851_MICALGS = Collections.unmodifiableMap(oldMicAlgs);

        STANDARD_MICALGS = RFC5751_MICALGS;
    }

    public static class Builder
    {
        private static final String[] detHeaders;
        private static final String[] detValues;
        private static final String[] encHeaders;
        private static final String[] encValues;

        static
        {
            detHeaders = new String[]
                {
                    "Content-Type"
                };

            detValues = new String[]
                {
                    "multipart/signed; protocol=\"application/pkcs7-signature\"",
                };

            encHeaders = new String[]
                {
                    "Content-Type",
                    "Content-Disposition",
                    "Content-Transfer-Encoding",
                    "Content-Description"
                };

            encValues = new String[]
                {
                    "application/pkcs7-mime; name=\"smime.p7m\"; smime-type=enveloped-data",
                    "attachment; filename=\"smime.p7m\"",
                    "base64",
                    "S/MIME Signed Message"
                };
        }

        private final CMSSignedDataStreamGenerator sigGen = new CMSSignedDataStreamGenerator();
        private final Map extraHeaders = new LinkedHashMap();
        private final boolean encapsulated;
        private final Map micAlgs = STANDARD_MICALGS;
        
        String contentTransferEncoding = "base64";

        public Builder()
        {
            this(false);
        }

        public Builder(
            boolean encapsulated)
        {
            this.encapsulated = encapsulated;
        }

        /**
         * Specify a MIME header (name, value) pair for this builder. If the headerName already exists it will
         * be overridden.
         *
         * @param headerName  name of the MIME header.
         * @param headerValue value of the MIME header.
         * @return the current Builder instance.
         */
        public Builder withHeader(String headerName, String headerValue)
        {
            this.extraHeaders.put(headerName, headerValue);

            return this;
        }

        public Builder addCertificate(X509CertificateHolder certificate)
            throws CMSException
        {
            this.sigGen.addCertificate(certificate);

            return this;
        }

        public Builder addCertificates(Store certificates)
            throws CMSException
        {
            this.sigGen.addCertificates(certificates);

            return this;
        }

        /**
         * Add a generator to produce the signer info required.
         *
         * @param signerGenerator a generator for a signer info object.
         * @return the current Builder instance.
         */
        public Builder addSignerInfoGenerator(SignerInfoGenerator signerGenerator)
        {
            this.sigGen.addSignerInfoGenerator(signerGenerator);

            return this;
        }

        public SMIMESignedWriter build(OutputStream mimeOut)
        {
            Map headers = new LinkedHashMap();

            String boundary;
            if (encapsulated)
            {
                boundary = null;
                for (int i = 0; i != encHeaders.length; i++)
                {
                    headers.put(encHeaders[i], encValues[i]);
                }
            }
            else
            {
                boundary = generateBoundary();

                // handle Content-Type specially
                StringBuffer contValue = new StringBuffer(detValues[0]);

                addHashHeader(contValue, sigGen.getDigestAlgorithms());

                addBoundary(contValue, boundary);
                headers.put(detHeaders[0], contValue.toString());

                for (int i = 1; i < detHeaders.length; i++)
                {
                    headers.put(detHeaders[i], detValues[i]);
                }
            }

            for (Iterator it = extraHeaders.entrySet().iterator(); it.hasNext();)
            {
                Map.Entry ent = (Map.Entry)it.next();
                headers.put((String)ent.getKey(), (String)ent.getValue());
            }

            return new SMIMESignedWriter(this, headers, boundary, mimeOut);
        }

        private void addHashHeader(
            StringBuffer header,
            List signers)
        {
            int count = 0;

            //
            // build the hash header
            //
            Iterator it = signers.iterator();
            Set micAlgSet = new TreeSet();

            while (it.hasNext())
            {
                AlgorithmIdentifier digest = (AlgorithmIdentifier)it.next();

                String micAlg = (String)micAlgs.get(digest.getAlgorithm());

                if (micAlg == null)
                {
                    micAlgSet.add("unknown");
                }
                else
                {
                    micAlgSet.add(micAlg);
                }
            }

            it = micAlgSet.iterator();

            while (it.hasNext())
            {
                String alg = (String)it.next();

                if (count == 0)
                {
                    if (micAlgSet.size() != 1)
                    {
                        header.append("; micalg=\"");
                    }
                    else
                    {
                        header.append("; micalg=");
                    }
                }
                else
                {
                    header.append(',');
                }

                header.append(alg);

                count++;
            }

            if (count != 0)
            {
                if (micAlgSet.size() != 1)
                {
                    header.append('\"');
                }
            }
        }

        private void addBoundary(
             StringBuffer header,
             String boundary)
        {
             header.append(";\r\n\tboundary=\"");
             header.append(boundary);
             header.append("\"");
        }

        private String generateBoundary()
        {
            SecureRandom random = new SecureRandom();

            return "==" + new BigInteger(180, random).setBit(179).toString(16) + "=";
        }
    }

    private final CMSSignedDataStreamGenerator sigGen;

    private final String boundary;
    private final OutputStream mimeOut;
    private final String contentTransferEncoding;

    private SMIMESignedWriter(Builder builder, Map headers, String boundary, OutputStream mimeOut)
    {
        super(new Headers(mapToLines(headers), builder.contentTransferEncoding));

        this.sigGen = builder.sigGen;
        this.contentTransferEncoding = builder.contentTransferEncoding;
        this.boundary = boundary;
        this.mimeOut = mimeOut;
    }

    /**
     * Return a content stream for the signer - note data written to this stream needs to properly
     * canonicalised if necessary.
     *
     * @return an output stream for data to be signed to be written to.
     * @throws IOException on a stream error.
     */
    public OutputStream getContentStream()
        throws IOException
    {
        headers.dumpHeaders(mimeOut);

        mimeOut.write(Strings.toByteArray("\r\n"));

        if (boundary == null)
        {
            return null; // TODO: new ContentOutputStream(sigGen.open(mimeOut, true), mimeOut);
        }
        else
        {
            mimeOut.write(Strings.toByteArray("This is an S/MIME signed message\r\n"));
            mimeOut.write(Strings.toByteArray("\r\n--"));
            mimeOut.write(Strings.toByteArray(boundary));
            mimeOut.write(Strings.toByteArray("\r\n"));

            ByteArrayOutputStream bOut = new ByteArrayOutputStream();

            Base64OutputStream stream = new Base64OutputStream(bOut);

            return new ContentOutputStream(sigGen.open(stream,false, SMimeUtils.createUnclosable(mimeOut)), mimeOut, bOut, stream);
        }
    }

    private class ContentOutputStream
        extends OutputStream
    {
        private final OutputStream main;
        private final OutputStream backing;
        private final ByteArrayOutputStream sigStream;
        private final OutputStream sigBase;

        ContentOutputStream(OutputStream main, OutputStream backing, ByteArrayOutputStream sigStream, OutputStream sigBase)
        {
            this.main = main;
            this.backing = backing;
            this.sigStream = sigStream;
            this.sigBase = sigBase;
        }

        public void write(int i)
            throws IOException
        {
            main.write(i);
        }

        public void close()
            throws IOException
        {
            if (boundary != null)
            {
                main.close();

                backing.write(Strings.toByteArray("\r\n--"));
                backing.write(Strings.toByteArray(boundary));
                backing.write(Strings.toByteArray("\r\n"));

                backing.write(Strings.toByteArray("Content-Type: application/pkcs7-signature; name=\"smime.p7s\"\r\n"));
                backing.write(Strings.toByteArray("Content-Transfer-Encoding: base64\r\n"));
                backing.write(Strings.toByteArray("Content-Disposition: attachment; filename=\"smime.p7s\"\r\n"));
                backing.write(Strings.toByteArray("\r\n"));

                if (sigBase != null)
                {
                    sigBase.close();
                }
                
                backing.write(sigStream.toByteArray());

                backing.write(Strings.toByteArray("\r\n--"));
                backing.write(Strings.toByteArray(boundary));
                backing.write(Strings.toByteArray("--\r\n"));
            }

            if (backing != null)
            {
                backing.close();
            }
        }
    }
}




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