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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.OutputStream;
import java.security.KeyPair;
import java.security.Security;
import java.security.cert.CertificateException;
import java.security.cert.X509Certificate;
import java.util.Collection;
import java.util.Iterator;

import junit.framework.TestCase;
import org.bouncycastle.cert.X509CertificateHolder;
import org.bouncycastle.cert.jcajce.JcaX509CertificateHolder;
import org.bouncycastle.cms.CMSException;
import org.bouncycastle.cms.SignerInformation;
import org.bouncycastle.cms.SignerInformationStore;
import org.bouncycastle.cms.jcajce.JcaSignerId;
import org.bouncycastle.cms.jcajce.JcaSimpleSignerInfoGeneratorBuilder;
import org.bouncycastle.cms.jcajce.JcaSimpleSignerInfoVerifierBuilder;
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.SMIMESignedWriter;
import org.bouncycastle.mime.smime.SMimeParserListener;
import org.bouncycastle.mime.smime.SMimeParserProvider;
import org.bouncycastle.operator.OperatorCreationException;
import org.bouncycastle.operator.bc.BcDigestCalculatorProvider;
import org.bouncycastle.util.Store;
import org.bouncycastle.util.Strings;
import org.bouncycastle.util.encoders.Base64;
import org.bouncycastle.util.io.Streams;

public class TestSMIMESigned
    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 _signCert;
    private static X509Certificate _reciCert;

    private static boolean _initialised = false;

    private static final byte[] simpleMessage = Strings.toByteArray(
        "Content-Type: text/plain; name=null; charset=us-ascii\r\n" +
            "Content-Transfer-Encoding: 7bit\r\n" +
            "Content-Disposition: inline; filename=null\r\n" +
            "\r\n" +
            "Hello, world!\r\n");

    private static final byte[] simpleMessageContent = Strings.toByteArray(
            "Hello, world!\r\n");

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

    private static final byte[] testMultipartMessageContent = Base64.decode(
        "LS0tLS0tPV9QYXJ0XzBfMjYwMzk2Mzg2LjEzNTI5MDQ3NTAxMzINCkNvbnRlbnQtVHlwZTogdGV4dC9w" +
            "bGFpbjsgbmFtZT1udWxsOyBjaGFyc2V0PXVzLWFzY2lpDQpDb250ZW50LVRyYW5zZmVyLUVuY29kaW5n" +
            "OiA3Yml0DQpDb250ZW50LURpc3Bvc2l0aW9uOiBpbmxpbmU7IGZpbGVuYW1lPW51bGwNCg0KQ2lhbyBm" +
            "cm9tIHZpZW5uYQ0KLS0tLS0tPV9QYXJ0XzBfMjYwMzk2Mzg2LjEzNTI5MDQ3NTAxMzItLQ0K");

    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();
            _signCert = CMSTestUtil.makeCertificate(_signKP, _signDN, _signKP, _signDN);

            _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 testSimpleGeneration()
        throws Exception
    {
        generationTest(simpleMessage, simpleMessageContent);
    }

    public void testEmbeddedMultipartGeneration()
        throws Exception
    {
        generationTest(testMultipartMessage, testMultipartMessageContent);
    }

    private void generationTest(byte[] message, final byte[] messageContent)
        throws Exception
    {
        //
        // output
        //
        ByteArrayOutputStream bOut = new ByteArrayOutputStream();
        SMIMESignedWriter.Builder sigBldr = new SMIMESignedWriter.Builder();

        sigBldr.addCertificate(new JcaX509CertificateHolder(_signCert));
        
        sigBldr.addSignerInfoGenerator(new JcaSimpleSignerInfoGeneratorBuilder().setProvider(BC).build("SHA256withRSA", _signKP.getPrivate(), _signCert));

        SMIMESignedWriter sigWrt = sigBldr.build(bOut);

        OutputStream out = sigWrt.getContentStream();

        out.write(message);

        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 content(MimeParserContext parserContext, Headers headers, InputStream inputStream)
                throws IOException
            {
                byte[] content = Streams.readAll(inputStream);

                assertTrue(org.bouncycastle.util.Arrays.areEqual(messageContent, content));
            }

            public void signedData(MimeParserContext parserContext, Headers headers, Store certificates, Store CRLs, Store attributeCertificates, SignerInformationStore signers)
                throws IOException, CMSException
            {
                SignerInformation signerInfo = signers.get(new JcaSignerId(_signCert));

                assertNotNull(signerInfo);

                Collection certCollection = certificates.getMatches(signerInfo.getSID());

                Iterator certIt = certCollection.iterator();
                X509CertificateHolder certHolder = (X509CertificateHolder)certIt.next();

                try
                {
                    assertEquals(true, signerInfo.verify(new JcaSimpleSignerInfoVerifierBuilder().setProvider("BC").build(certHolder)));
                }
                catch (OperatorCreationException e)
                {
                    throw new CMSException(e.getMessage(), e);
                }
                catch (CertificateException e)
                {
                    throw new CMSException(e.getMessage(), e);
                }

                dataParsed.markDone();
            }
        });

        assertTrue(dataParsed.isDone());
    }
}