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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 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.mime.test;

import java.io.ByteArrayOutputStream;
import java.io.IOException;
import java.io.InputStream;
import java.io.InputStreamReader;
import java.io.OutputStream;
import java.security.KeyPair;
import java.security.PrivateKey;
import java.security.Security;
import java.security.cert.CertificateFactory;
import java.security.cert.X509Certificate;

import junit.framework.TestCase;
import org.bouncycastle.cms.CMSAlgorithm;
import org.bouncycastle.cms.CMSException;
import org.bouncycastle.cms.OriginatorInformation;
import org.bouncycastle.cms.RecipientInformation;
import org.bouncycastle.cms.RecipientInformationStore;
import org.bouncycastle.cms.jcajce.JceCMSContentEncryptorBuilder;
import org.bouncycastle.cms.jcajce.JceKeyTransEnvelopedRecipient;
import org.bouncycastle.cms.jcajce.JceKeyTransRecipientId;
import org.bouncycastle.cms.jcajce.JceKeyTransRecipientInfoGenerator;
import org.bouncycastle.cms.test.CMSTestUtil;
import org.bouncycastle.jce.provider.BouncyCastleProvider;
import org.bouncycastle.mime.Headers;
import org.bouncycastle.mime.MimeParser;
import org.bouncycastle.mime.MimeParserContext;
import org.bouncycastle.mime.MimeParserProvider;
import org.bouncycastle.mime.smime.SMIMEEnvelopedWriter;
import org.bouncycastle.mime.smime.SMimeParserListener;
import org.bouncycastle.mime.smime.SMimeParserProvider;
import org.bouncycastle.openssl.PEMKeyPair;
import org.bouncycastle.openssl.PEMParser;
import org.bouncycastle.openssl.jcajce.JcaPEMKeyConverter;
import org.bouncycastle.operator.bc.BcDigestCalculatorProvider;
import org.bouncycastle.util.encoders.Base64;
import org.bouncycastle.util.io.Streams;

public class TestSMIMEEnveloped
    extends TestCase
{
    private static final String BC = BouncyCastleProvider.PROVIDER_NAME;

    private static String          _signDN;
    private static KeyPair          _signKP;

    private static String          _reciDN;
    private static KeyPair          _reciKP;

    private static X509Certificate _reciCert;

    private static boolean         _initialised = false;

    private static final byte[] testMessage = Base64.decode(
        "TUlNRS1WZXJzaW9uOiAxLjANCkNvbnRlbnQtVHlwZTogbXVsdGlwYXJ0L21peGVkOyANCglib3VuZGFye" +
        "T0iLS0tLT1fUGFydF8wXzI2MDM5NjM4Ni4xMzUyOTA0NzUwMTMyIg0KQ29udGVudC1MYW5ndWFnZTogZW" +
        "4NCkNvbnRlbnQtRGVzY3JpcHRpb246IEEgbWFpbCBmb2xsb3dpbmcgdGhlIERJUkVDVCBwcm9qZWN0IHN" +
        "wZWNpZmljYXRpb25zDQoNCi0tLS0tLT1fUGFydF8wXzI2MDM5NjM4Ni4xMzUyOTA0NzUwMTMyDQpDb250" +
        "ZW50LVR5cGU6IHRleHQvcGxhaW47IG5hbWU9bnVsbDsgY2hhcnNldD11cy1hc2NpaQ0KQ29udGVudC1Uc" +
        "mFuc2Zlci1FbmNvZGluZzogN2JpdA0KQ29udGVudC1EaXNwb3NpdGlvbjogaW5saW5lOyBmaWxlbmFtZT" +
        "1udWxsDQoNCkNpYW8gZnJvbSB2aWVubmENCi0tLS0tLT1fUGFydF8wXzI2MDM5NjM4Ni4xMzUyOTA0NzU" +
        "wMTMyLS0NCg==");

    private static void init()
        throws Exception
    {
        if (!_initialised)
        {
            if (Security.getProvider("BC") == null)
            {
                Security.addProvider(new BouncyCastleProvider());
            }

            _initialised = true;

            _signDN   = "O=Bouncy Castle, C=AU";
            _signKP   = CMSTestUtil.makeKeyPair();

            _reciDN   = "CN=Doug, OU=Sales, O=Bouncy Castle, C=AU";
            _reciKP   = CMSTestUtil.makeKeyPair();
            _reciCert = CMSTestUtil.makeCertificate(_reciKP, _reciDN, _signKP, _signDN);
        }
    }

    public void setUp()
        throws Exception
    {
        init();
    }
    
    public void testSMIMEEnveloped()
        throws Exception
    {
        InputStream inputStream = this.getClass().getResourceAsStream("test256.message");

        MimeParserProvider provider = new SMimeParserProvider("7bit", new BcDigestCalculatorProvider());

        MimeParser p = provider.createParser(new ReadOnceInputStream(Streams.readAll(inputStream)));

        final TestDoneFlag dataParsed = new TestDoneFlag();

        p.parse(new SMimeParserListener()
        {
            public void envelopedData(MimeParserContext parserContext, Headers headers, OriginatorInformation originator, RecipientInformationStore recipients)
                throws IOException, CMSException
            {
                RecipientInformation recipInfo = recipients.get(new JceKeyTransRecipientId(loadCert("cert.pem")));

                assertNotNull(recipInfo);

                byte[] content = recipInfo.getContent(new JceKeyTransEnvelopedRecipient(loadKey("key.pem")));
                assertTrue(org.bouncycastle.util.Arrays.areEqual(testMessage, content));

                dataParsed.markDone();
            }
        });

        assertTrue(dataParsed.isDone());
    }

    public void testKeyTransAES128()
        throws Exception
    {
        //
        // output
        //
        ByteArrayOutputStream bOut = new ByteArrayOutputStream();
        SMIMEEnvelopedWriter.Builder envBldr = new SMIMEEnvelopedWriter.Builder();

        envBldr.addRecipientInfoGenerator(new JceKeyTransRecipientInfoGenerator(_reciCert).setProvider(BC));

        SMIMEEnvelopedWriter envWrt = envBldr.build(bOut, new JceCMSContentEncryptorBuilder(CMSAlgorithm.AES128_CBC).setProvider(BC).build());

        OutputStream out = envWrt.getContentStream();

        out.write(testMessage);

        out.close();
        
        //
        // parse
        //
        final TestDoneFlag dataParsed = new TestDoneFlag();

        MimeParserProvider provider = new SMimeParserProvider("7bit", new BcDigestCalculatorProvider());

        MimeParser p = provider.createParser(new ReadOnceInputStream(bOut.toByteArray()));

        p.parse(new SMimeParserListener()
        {
            public void envelopedData(MimeParserContext parserContext, Headers headers, OriginatorInformation originator, RecipientInformationStore recipients)
                throws IOException, CMSException
            {
                RecipientInformation recipInfo = recipients.get(new JceKeyTransRecipientId(_reciCert));

                assertNotNull(recipInfo);

                byte[] content = recipInfo.getContent(new JceKeyTransEnvelopedRecipient(_reciKP.getPrivate()));
                assertTrue(org.bouncycastle.util.Arrays.areEqual(testMessage, content));

                dataParsed.markDone();
            }
        });

        assertTrue(dataParsed.isDone());
    }

    private X509Certificate loadCert(String name)
        throws IOException
    {
        try
        {
            return (X509Certificate)CertificateFactory.getInstance("X.509", "BC").generateCertificate(getClass().getResourceAsStream(name));
        }
        catch (Exception e)
        {
            throw new IOException(e.getMessage());
        }
    }

    private PrivateKey loadKey(String name)
        throws IOException
    {
        return new JcaPEMKeyConverter().setProvider("BC").getKeyPair((PEMKeyPair)(new PEMParser(new InputStreamReader(getClass().getResourceAsStream(name)))).readObject()).getPrivate();
    }
}