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The Bouncy Castle Java S/MIME APIs for handling S/MIME protocols. This jar contains S/MIME 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. The JavaMail API and the Java activation framework will also be needed.

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package org.bouncycastle.mail.smime.examples;

import java.io.File;
import java.io.FileOutputStream;
import java.security.KeyStore;
import java.security.cert.Certificate;
import java.security.cert.X509Certificate;
import java.util.Properties;

import javax.activation.DataHandler;
import javax.activation.FileDataSource;
import javax.mail.Address;
import javax.mail.Message;
import javax.mail.Session;
import javax.mail.internet.InternetAddress;
import javax.mail.internet.MimeBodyPart;
import javax.mail.internet.MimeMessage;

import org.bouncycastle.cms.CMSAlgorithm;
import org.bouncycastle.cms.jcajce.JceCMSContentEncryptorBuilder;
import org.bouncycastle.cms.jcajce.JceKeyTransRecipientInfoGenerator;
import org.bouncycastle.mail.smime.SMIMEEnvelopedGenerator;

/**
 * a simple example that creates a single encrypted mail message.
 * 
 * The key store can be created using the class in
 * org.bouncycastle.jce.examples.PKCS12Example - the program expects only one
 * key to be present in the key file.
 * 
 * Note: while this means that both the private key is available to
 * the program, the private key is retrieved from the keystore only for
 * the purposes of locating the corresponding public key, in normal circumstances
 * you would only be doing this with a certificate available.
 */
public class CreateLargeEncryptedMail
{
    public static void main(
        String args[])
        throws Exception
    {
        if (args.length != 3)
        {
            System.err.println("usage: CreateLargeEncryptedMail pkcs12Keystore password inputFile");
            System.exit(0);
        }

        //
        // Open the key store
        //
        KeyStore    ks = KeyStore.getInstance("PKCS12", "BC");
        String      keyAlias = ExampleUtils.findKeyAlias(ks, args[0], args[1].toCharArray());

        Certificate[]   chain = ks.getCertificateChain(keyAlias);

        //
        // create the generator for creating an smime/encrypted message
        //
        SMIMEEnvelopedGenerator  gen = new SMIMEEnvelopedGenerator();
          
        gen.addRecipientInfoGenerator(new JceKeyTransRecipientInfoGenerator((X509Certificate)chain[0]).setProvider("BC"));

        //
        // create a subject key id - this has to be done the same way as
        // it is done in the certificate associated with the private key
        // version 3 only.
        //
        /*
        MessageDigest           dig = MessageDigest.getInstance("SHA1", "BC");

        dig.update(cert.getPublicKey().getEncoded());
              
        gen.addKeyTransRecipient(cert.getPublicKey(), dig.digest());
        */
         
        //
        // create the base for our message
        //
        MimeBodyPart    msg = new MimeBodyPart();

        msg.setDataHandler(new DataHandler(new FileDataSource(new File(args[2]))));
        msg.setHeader("Content-Type", "application/octet-stream");
        msg.setHeader("Content-Transfer-Encoding", "binary");

        MimeBodyPart mp = gen.generate(msg, new JceCMSContentEncryptorBuilder(CMSAlgorithm.RC2_CBC).setProvider("BC").build());
        
        //
        // Get a Session object and create the mail message
        //
        Properties props = System.getProperties();
        Session session = Session.getDefaultInstance(props, null);

        Address fromUser = new InternetAddress("\"Eric H. Echidna\"");
        Address toUser = new InternetAddress("[email protected]");

        MimeMessage body = new MimeMessage(session);
        body.setFrom(fromUser);
        body.setRecipient(Message.RecipientType.TO, toUser);
        body.setSubject("example encrypted message");
        body.setContent(mp.getContent(), mp.getContentType());
        body.saveChanges();

        body.writeTo(new FileOutputStream("encrypted.message"));
    }
}