Using Outlook 2010 to view S/MIME mails - outlook

Question

I am trying to send an S/MIME signed and encrypted mail to myself from Java Mail (bouncy castle 1.51) to my outlook.
I am able to send the mail fine but receiving is an issue as Outlook doesn't want to open the mail. The following is the error I get when trying to open:
Cannot open this item. Your Digital ID name cannot be found by the underlying security system.
The same mail (saved to a local file in eml format) is viewable fine with p7m Viewer, indicating that the P12 certificate has been installed correctly on my laptop. I have installed the same P12 file that I am using as Keystore in my Java Mail code.
Am I doing anything wrong? Is the issue at Outlook end? I am using Office 365 and wanted to add that p7m Viewer is also not able to open the smime.p7m that I download from the Outlook WebMail. The error I receive is:
The file is corrupted; Signature information might be missing.
Below is the Java code I am using to encrypt / send mail.
public class BCTest {
public static final String pkcs12Keystore = "C:/Development/Workspace/BouncyCastle_SecureMail/resources/cert/StartCom.p12";
public static final String ksPassword = "ksPassword";
public static final String sendFile = "C:/Development/Workspace/BouncyCastle_SecureMail/resources/hello.txt";
public static final String outputFile = "C:/Development/Workspace/BouncyCastle_SecureMail/output/Encrypted.eml";
public static final String message = "Hi There!!";
public static final String frAddress = "email#domain.com";
public static final String toAddress = "email#domain.com";
public static final String host = "outlook.office365.com";
public static final int port = 587;
public static final String userName = "email#domain.com";
public static final String password = "password";
public static void main(String[] args) {
send();
}
public static void send() {
try {
System.out.println("Setting Mailcap");
MailcapCommandMap mailcap = (MailcapCommandMap) CommandMap.getDefaultCommandMap();
mailcap.addMailcap("application/pkcs7-signature;; x-java-content-handler=org.bouncycastle.mail.smime.handlers.pkcs7_signature");
mailcap.addMailcap("application/pkcs7-mime;; x-java-content-handler=org.bouncycastle.mail.smime.handlers.pkcs7_mime");
mailcap.addMailcap("application/x-pkcs7-signature;; x-java-content-handler=org.bouncycastle.mail.smime.handlers.x_pkcs7_signature");
mailcap.addMailcap("application/x-pkcs7-mime;; x-java-content-handler=org.bouncycastle.mail.smime.handlers.x_pkcs7_mime");
mailcap.addMailcap("multipart/signed;; x-java-content-handler=org.bouncycastle.mail.smime.handlers.multipart_signed");
CommandMap.setDefaultCommandMap(mailcap);
/* Add BC */
System.out.println("Setting Bouncy Castle as provider");
Security.addProvider(new BouncyCastleProvider());
/* Open the keystore */
System.out.println("Opening the keystore: " + pkcs12Keystore + " using password " + ksPassword);
KeyStore keystore = KeyStore.getInstance("PKCS12", "BC");
keystore.load(new FileInputStream(pkcs12Keystore), ksPassword.toCharArray());
// Find the first legit alias in the keystore and use it
System.out.println("Getting the keystore alias");
Enumeration<String> e = keystore.aliases();
String keyAlias = null;
while (e.hasMoreElements() && (keyAlias == null)) {
String alias = e.nextElement();
keyAlias = keystore.isKeyEntry(alias) ? alias : null;
}
if (keyAlias == null) {
throw new Exception("Can't find a private key!");
}
Certificate[] chain = keystore.getCertificateChain(keyAlias);
/* Get the private key to sign the message with */
System.out.println("Getting the private key");
PrivateKey privateKey = (PrivateKey) keystore.getKey(keyAlias, ksPassword.toCharArray());
if (privateKey == null) {
throw new Exception("No private key for alias: " + keyAlias);
}
/* Create Email body */
System.out.println("Creating the Email body");
MimeBodyPart messageBodyPart = new MimeBodyPart();
messageBodyPart.setContent(message, "text/html");
/* Attach the file to encrypt */
System.out.println("Creating the attachment");
FileDataSource fds = new FileDataSource(sendFile);
MimeBodyPart attachPart = new MimeBodyPart();
attachPart.setDataHandler(new DataHandler(fds));
attachPart.setFileName(fds.getName());
System.out.println("Adding body & attachment to mail");
MimeMultipart bodyMulti = new MimeMultipart();
bodyMulti.addBodyPart(messageBodyPart);
bodyMulti.addBodyPart(attachPart);
System.out.println("Setting mail properties");
Session session = Session.getDefaultInstance(System.getProperties());
MimeMessage body = new MimeMessage(session);
body.setFrom(new InternetAddress(frAddress));
body.setRecipient(Message.RecipientType.TO, new InternetAddress(toAddress));
body.setSentDate(new Date());
body.setSubject("Encrypted Mail");
body.setContent(bodyMulti, bodyMulti.getContentType());
body.saveChanges();
/* Create the SMIMESignedGenerator */
System.out.println("Creating the SMIMESignedGenerator");
SMIMECapabilityVector capabilities = new SMIMECapabilityVector();
capabilities.addCapability(SMIMECapability.dES_EDE3_CBC);
capabilities.addCapability(SMIMECapability.rC2_CBC, 128);
capabilities.addCapability(SMIMECapability.dES_CBC);
capabilities.addCapability(SMIMECapability.aES256_CBC);
System.out.println("Creating the ASN1EncodableVector");
ASN1EncodableVector attributes = new ASN1EncodableVector();
attributes.add(new SMIMEEncryptionKeyPreferenceAttribute(new IssuerAndSerialNumber(new X500Name(((X509Certificate) chain[0])
.getIssuerDN().getName()), ((X509Certificate) chain[0]).getSerialNumber())));
attributes.add(new SMIMECapabilitiesAttribute(capabilities));
System.out.println("Adding certificate");
List<X509Certificate> certList = new ArrayList<X509Certificate>();
certList.add((X509Certificate) chain[0]);
SMIMESignedGenerator gen = new SMIMESignedGenerator("binary");
gen.addSignerInfoGenerator(new JcaSimpleSignerInfoGeneratorBuilder().setProvider("BC").build("SHA1withRSA", privateKey,
(X509Certificate) chain[0]));
gen.addCertificates(new JcaCertStore(certList));
MimeMultipart multiPart = gen.generate(body);
MimeMessage signedMessage = new MimeMessage(session);
System.out.println("Creating Mime Message");
#SuppressWarnings("unchecked")
Enumeration<String> headers = body.getAllHeaderLines();
while (headers.hasMoreElements()) {
signedMessage.addHeaderLine(headers.nextElement());
}
signedMessage.setContent(multiPart);
signedMessage.saveChanges();
/* Create the encrypter and encrypt the message */
System.out.println("Encrypting Mime Message");
SMIMEEnvelopedGenerator fact = new SMIMEEnvelopedGenerator();
fact.addRecipientInfoGenerator(new JceKeyTransRecipientInfoGenerator((X509Certificate) chain[0]).setProvider("BC"));
MimeBodyPart encryptedPart = fact.generate(signedMessage, new JceCMSContentEncryptorBuilder(CMSAlgorithm.RC2_CBC, 40)
.setProvider("BC").build());
encryptedPart.setHeader("Content-Transfer-Encoding", "binary");
ByteArrayOutputStream out = new ByteArrayOutputStream();
encryptedPart.writeTo(out);
/* Create a new MimeMessage for the encrypted and signed content */
System.out.println("Setting mail server properties");
Properties props = new Properties();
props.put("mail.smtp.host", host);
props.put("mail.smtp.port", port);
props.put("mail.smtp.auth", "true");
props.put("mail.smtp.starttls.enable", "true");
Session smtpSession = Session.getInstance(props, new Authenticator() {
#Override
protected PasswordAuthentication getPasswordAuthentication() {
return new PasswordAuthentication(userName, password);
}
});
MimeMessage smtpMessage = new MimeMessage(smtpSession, new ByteArrayInputStream(out.toByteArray()));
smtpMessage.saveChanges();
/* Set all original MIME headers in the encrypted message */
#SuppressWarnings("unchecked")
Enumeration<String> orgHeaders = body.getAllHeaderLines();
while (orgHeaders.hasMoreElements()) {
String headerLine = (String) orgHeaders.nextElement();
/* Do not override content-* headers from the original message */
if (!Strings.toLowerCase(headerLine).startsWith("content-")) {
smtpMessage.addHeaderLine(headerLine);
}
}
System.out.println("Creating eml file as location: " + outputFile);
smtpMessage.writeTo(new FileOutputStream(outputFile));
System.out.println("Sending Mail");
Transport.send(smtpMessage);
System.out.println("Mail Sent");
} catch (SMIMEException ex) {
ex.getUnderlyingException().printStackTrace(System.err);
ex.printStackTrace(System.err);
} catch (Exception ex) {
ex.printStackTrace(System.err);
}
}
}
Plz help!!!
Regards

Answer 1

It sounds like you need to import your private key (in .p12 format) into Outlook's Personal trust store. Here is how to do that:
Import your personal certificate:
From the Tools menu, select Internet Options. Open the Content tab,
and click Certificates. In the Certificates window, select your
certificate and click Import. Work through the Certificate Import
Wizard to import your certificate file. When browsing for the correct
file, change the "Files of type" field from *.cer, *.crt to *.pfx,
*.p12. You will be prompted for the password used to encrypt the private key when the certificate was initially exported. Enter it. You
will want to select the Enable strong private key protection and Mark
this key as exportable radio buttons. You can select whatever storage
you want. It's easiest to put all the certificates in the Personal
store. Click Finish to exit the wizard. It will take a moment to
execute the import. A window pops up to say the application is
creating a protected item, and for you to select the security level.
Leaving it at medium (the default) is fine. Click OK. A window pops up
to say the import was successful. Click OK.
source: https://fermi.service-now.com/kb_view.do?sysparm_article=KB0010813