I am trying to send the smime signed and encrypted mail using my email IDs. I got two smime certificates each for my two Gmail IDs. I tried to use the SMIMETestUtil class for testing the scenario. I am successfully able to send mail from one email to another. But when I am trying to open it, I receive the error “Your digital ID name cannot be found by the underlying security system”.

I am using the below code.

package org.simplejavamail.utils.mail.smime;

import jakarta.mail.Authenticator;
import jakarta.mail.MessagingException;
import jakarta.mail.PasswordAuthentication;
import jakarta.mail.Session;
import jakarta.mail.internet.InternetAddress;
import jakarta.mail.internet.MimeMessage;
import jakarta.mail.internet.MimeMultipart;
import org.bouncycastle.cms.CMSAlgorithm;
import org.bouncycastle.jce.provider.BouncyCastleProvider;
import org.junit.Before;
import org.junit.Test;

import java.io.IOException;
import java.io.InputStream;
import java.security.KeyStoreException;
import java.security.NoSuchAlgorithmException;
import java.security.NoSuchProviderException;
import java.security.Security;
import java.security.cert.CertificateException;
import java.security.cert.X509Certificate;
import java.util.Arrays;
import java.util.Properties;

import static jakarta.mail.Transport.send;
import static org.assertj.core.api.Assertions.assertThat;

public class SmimeUtilTest {

private static final String SignatureAlgorithmRsaPss = "SHA256WITHRSAANDMGF1";
private SmimeKeyStore alicesKeyStore;
private SmimeKeyStore bobsKeyStore;
private Session mailSession;

@Before
public void setup() throws MessagingException, KeyStoreException, NoSuchProviderException, CertificateException, IOException, NoSuchAlgorithmException {
    Security.addProvider(new BouncyCastleProvider());
    InputStream alicesKeystoreStream = this.getClass().getClassLoader().getResourceAsStream("sh_cert.pfx");
    this.alicesKeyStore = new SmimeKeyStore(alicesKeystoreStream, "<mypass>".toCharArray());
    System.out.println(this.alicesKeyStore.getPrivateKeyAliases());
    InputStream bobsKeystoreStream = this.getClass().getClassLoader().getResourceAsStream("sho_cert.pfx");
    this.bobsKeyStore = new SmimeKeyStore(bobsKeystoreStream, "<mypass>".toCharArray());

    Properties props = new Properties();
    props.put("mail.smtp.host", "smtp.gmail.com");
    props.put("mail.smtp.socketFactory.port", "465");
    props.put("mail.smtp.socketFactory.class",
            "javax.net.ssl.SSLSocketFactory");
    props.put("mail.smtp.auth", "true");
    props.put("mail.smtp.port", "465");
    //get Session

    this.mailSession = Session.getDefaultInstance(props,
            new Authenticator() {
                protected PasswordAuthentication getPasswordAuthentication() {
                    return new PasswordAuthentication("<my id>","<my pass>");
                }
            });
}

private MimeMessage createTestMessage(String from, String to) throws MessagingException {
    MimeMessage testMessage = new MimeMessage(this.mailSession);
    testMessage.setFrom(new InternetAddress(from));
    testMessage.setRecipient(MimeMessage.RecipientType.TO, new InternetAddress(to));
    testMessage.setSubject("This is a test email");
    testMessage.setContent("This is some test content for the test email's body", "text/plain; charset=utf-8");
    return testMessage;
}

@Test
public void SuccessfullySignAndValidate() throws MessagingException, IOException {
    MimeMessage testMessage = createTestMessage("[email protected]", "[email protected]");
    SmimeKey alicesKey = this.alicesKeyStore.getPrivateKey("alice", "alice".toCharArray());
    MimeMessage signedMessage = SmimeUtil.sign(this.mailSession, null, testMessage, alicesKey);
    MimeMultipart multipartContent = (MimeMultipart) signedMessage.getContent();
    assertThat(SmimeUtil.getStatus(multipartContent)).isEqualTo(SmimeState.SIGNED);
    assertThat(SmimeUtil.checkSignature(multipartContent)).isTrue();
}

@Test
public void SuccessfullyEnvelopeAndDecryptDefault() throws MessagingException {
    MimeMessage testMessage = createTestMessage("<from-id>", "<to-id>");
    SmimeKey alicesKey = this.alicesKeyStore.getPrivateKey("<my alias>", "<my pass>".toCharArray());
    X509Certificate alicesCert = alicesKey.getCertificate();
    MimeMessage encryptedMessage = SmimeUtil.encrypt(this.mailSession, null,
            SmimeUtil.sign(this.mailSession, null, testMessage, alicesKey),
            alicesCert);


    send(encryptedMessage);

    assertThat(SmimeUtil.getStatus((encryptedMessage))).isEqualTo(SmimeState.ENCRYPTED);
    MimeMessage decryptedMessage = SmimeUtil.decrypt(this.mailSession, encryptedMessage, alicesKey);
    assertThat(SmimeUtil.checkSignature(decryptedMessage)).isTrue();
}

@Test
public void SuccessfullyEnvelopeAndDecrypt() throws MessagingException {
    MimeMessage testMessage = createTestMessage("[email protected]", "[email protected]");
    SmimeKey alicesKey = this.alicesKeyStore.getPrivateKey("alice", "alice".toCharArray());
    X509Certificate alicesCert = alicesKey.getCertificate();
    MimeMessage encryptedMessage = SmimeUtil.encrypt(this.mailSession,
            SmimeUtil.sign(this.mailSession, null, testMessage, alicesKey, SignatureAlgorithmRsaPss),
            null, alicesCert, KeyEncapsulationAlgorithm.RSA_OAEP_SHA256, CMSAlgorithm.AES256_CBC);
    assertThat(SmimeUtil.getStatus((encryptedMessage))).isEqualTo(SmimeState.ENCRYPTED);
    MimeMessage decryptedMessage = SmimeUtil.decrypt(this.mailSession, encryptedMessage, alicesKey);
    assertThat(SmimeUtil.checkSignature(decryptedMessage)).isTrue();
}

@Test
public void AliceToBoEnvelopeAndDecrypt() throws MessagingException {
    MimeMessage testMessage = createTestMessage("<from-id>", "<to-id>");
    SmimeKey alicesKey = this.alicesKeyStore.getPrivateKey("<my alias>", "<my pass>".toCharArray());
    SmimeKey bobsKey = this.bobsKeyStore.getPrivateKey("<my alias>", "<my pass>".toCharArray());
    X509Certificate bobsCert = bobsKey.getCertificate();
    System.out.println(Arrays.toString(bobsCert.getKeyUsage()));
    MimeMessage encryptedMessage = SmimeUtil.encrypt(this.mailSession,
            SmimeUtil.sign(this.mailSession, null, testMessage, alicesKey, SignatureAlgorithmRsaPss),
            null, bobsCert, KeyEncapsulationAlgorithm.RSA_OAEP_SHA512, CMSAlgorithm.AES256_GCM);

     send(encryptedMessage);
}

@Test
public void BobToAliceEnvelopeAndDecrypt() throws MessagingException {
    MimeMessage testMessage = createTestMessage("[email protected]", "[email protected]");
    SmimeKey bobsKey = this.bobsKeyStore.getPrivateKey("bob", "bob".toCharArray());
    SmimeKey alicesKey = this.alicesKeyStore.getPrivateKey("alice", "alice".toCharArray());
    X509Certificate alicesCert = alicesKey.getCertificate();
    MimeMessage encryptedMessage = SmimeUtil.encrypt(this.mailSession,
            SmimeUtil.sign(this.mailSession, null, testMessage, bobsKey, SignatureAlgorithmRsaPss),
            null, alicesCert, KeyEncapsulationAlgorithm.RSA_OAEP_SHA384, CMSAlgorithm.AES192_CCM);
    assertThat(SmimeUtil.getStatus((encryptedMessage))).isEqualTo(SmimeState.ENCRYPTED);
    MimeMessage decryptedMessage = SmimeUtil.decrypt(this.mailSession, encryptedMessage, alicesKey);
    assertThat(SmimeUtil.checkSignature(decryptedMessage)).isTrue();
}
}

Error Image

Installed both smime certificates in local machine but still not able open the mail and getting the same issue. I expect to open signed and encrypted mail successfully.