Exchange server will not accept username/password provided with javax.mail API

Question

I have a lovely little Java client that sends signed email messages. We have an Exchange server that requires username/password authentication to send a message. When I connect to the exchange server, I get this error: ``` avax.mail.AuthenticationFailedException: failed to connect at javax.mail.Service.connect(Service.java:322) at javax.mail.Service.connect(Service.java:172) ``` When I connect to other servers (Unix servers), I have no problem. Below is the full debug trace. I can't figure it out. ``` DEBUG: JavaMail version 1.4.2 DEBUG: successfully loaded resource: /META-INF/javamail.default.providers DEBUG: Tables of loaded providers DEBUG: Providers Listed By Class Name: {com.sun.mail.smtp.SMTPSSLTransport=javax.mail.Provider[TRANSPORT,smtps,com.sun.mail.smtp.SM} DEBUG: Providers Listed By Protocol: {imaps=javax.mail.Provider[STORE,imaps,com.sun.mail.imap.IMAPSSLStore,Sun Microsystems, Inc], } DEBUG: successfully loaded resource: /META-INF/javamail.default.address.map DEBUG: getPr…

Accepted Answer

Apparently, MS Exchange SSL connection is not established properly by Java Mail API. It relies on using `SSLSocketFactory` for that, but, if I remember correctly, MS Exchange requires a somewhat mixed approach.

Anyway, I have this piece of code in one of my projects:

```
import javax.net.SocketFactory;
import javax.net.ssl.SSLContext;
import javax.net.ssl.SSLSocketFactory;
import javax.net.ssl.TrustManager;
import javax.net.ssl.*;
import java.io.IOException;
import java.net.InetAddress;
import java.net.Socket;
import java.security.cert.CertificateException;
import java.security.cert.X509Certificate;

public class ExchangeSSLSocketFactory extends SSLSocketFactory {

private SSLSocketFactory sslSocketFactory;
private SocketFactory socketFactory;

public ExchangeSSLSocketFactory() {
    try {
        socketFactory = SocketFactory.getDefault();

SSLContext context = SSLContext.getInstance("TLS");
        context.init(null, new TrustManager[] { new EmptyTrustManager() }, null);
        sslSocketFactory = (SSLSocketFactory)context.getSocketFactory();
    }
    catch (Exception e) {
        throw new RuntimeException(e);
    }
}

private final class EmptyTrustManager implements X509TrustManager {
    public void checkClientTrusted(X509Certificate[] cert, String authType) throws CertificateException {}

public void checkServerTrusted(X509Certificate[] cert, String authType) throws CertificateException {}

public X509Certificate[] getAcceptedIssuers() {
        return new java.security.cert.X509Certificate[0];
    }
}

public static SocketFactory getDefault() {
    return new ExchangeSSLSocketFactory();
}

@Override
public Socket createSocket(Socket socket, String s, int i, boolean flag) throws IOException {
    return sslSocketFactory.createSocket(socket, s, i, flag);
}

@Override
public Socket createSocket(InetAddress inaddr, int i, InetAddress inaddr1, int j) throws IOException {
    return socketFactory.createSocket(inaddr, i, inaddr1, j);
}

@Override
public Socket createSocket(InetAddress inaddr, int i) throws IOException {
    return socketFactory.createSocket(inaddr, i);
}

@Override
public Socket createSocket(String s, int i, InetAddress inaddr, int j) throws IOException {
    return socketFactory.createSocket(s, i, inaddr, j);
}

@Override
public Socket createSocket(String s, int i) throws IOException {
    return socketFactory.createSocket(s, i);
}

@Override
public Socket createSocket() throws IOException {
    return socketFactory.createSocket();
}

@Override
public String[] getDefaultCipherSuites() {
    return sslSocketFactory.getSupportedCipherSuites();
}

@Override
public String[] getSupportedCipherSuites() {
    return sslSocketFactory.getSupportedCipherSuites();
}

}
```

You tell the Java Mail API to use this socket factory by setting following properties:

- `ssl.SocketFactory.provider`

- `mail.smtp.socketFactory.class`

to full class name of `ExchangeSSLSocketFactory`

From your debug output, it seems that you already have:

- `mail.smtp.starttls.enable` set to true

With all this in place, the problem should be solved.

Exchange server will not accept username/password provided with javax.mail API

Solution

Problem