Reload SSL context on file change for LDAP (#36937)

In #30509 we changed the way SSL configuration is reloaded when the
content of a file changes. As a consequence of that implementation
change the LDAP realm ceased to pick up changes to CA files (or other
certificate material) if they changed.

This commit repairs the reloading behaviour for LDAP realms, and adds
a test for this functionality.

Resolves: #36923

x-pack/plugin/core/src/main/java/org/elasticsearch/xpack/core/ssl/SSLService.java

@@ -52,6 +52,7 @@
 import java.util.Objects;
 import java.util.Optional;
 import java.util.Set;
+import java.util.function.Supplier;
 import java.util.stream.Collectors;
 
 /**
@@ -199,9 +200,14 @@ SSLIOSessionStrategy sslIOSessionStrategy(SSLContext sslContext, String[] protoc
      * @return Never {@code null}.
      */
     public SSLSocketFactory sslSocketFactory(SSLConfiguration configuration) {
-        SSLSocketFactory socketFactory = sslContext(configuration).getSocketFactory();
-        return new SecuritySSLSocketFactory(socketFactory, configuration.supportedProtocols().toArray(Strings.EMPTY_ARRAY),
-                supportedCiphers(socketFactory.getSupportedCipherSuites(), configuration.cipherSuites(), false));
+        final SSLContextHolder contextHolder = sslContextHolder(configuration);
+        SSLSocketFactory socketFactory = contextHolder.sslContext().getSocketFactory();
+        final SecuritySSLSocketFactory securitySSLSocketFactory = new SecuritySSLSocketFactory(
+            () -> contextHolder.sslContext().getSocketFactory(),
+            configuration.supportedProtocols().toArray(Strings.EMPTY_ARRAY),
+            supportedCiphers(socketFactory.getSupportedCipherSuites(), configuration.cipherSuites(), false));
+        contextHolder.addReloadListener(securitySSLSocketFactory::reload);
+        return securitySSLSocketFactory;
     }
 
     /**
@@ -453,12 +459,15 @@ public Set<CertificateInfo> getLoadedCertificates() throws GeneralSecurityExcept
      */
     private static class SecuritySSLSocketFactory extends SSLSocketFactory {
 
-        private final SSLSocketFactory delegate;
+        private final Supplier<SSLSocketFactory> delegateSupplier;
         private final String[] supportedProtocols;
         private final String[] ciphers;
 
-        SecuritySSLSocketFactory(SSLSocketFactory delegate, String[] supportedProtocols, String[] ciphers) {
-            this.delegate = delegate;
+        private volatile SSLSocketFactory delegate;
+
+        SecuritySSLSocketFactory(Supplier<SSLSocketFactory> delegateSupplier, String[] supportedProtocols, String[] ciphers) {
+            this.delegateSupplier = delegateSupplier;
+            this.delegate = this.delegateSupplier.get();
             this.supportedProtocols = supportedProtocols;
             this.ciphers = ciphers;
         }
@@ -515,6 +524,11 @@ public Socket createSocket(InetAddress address, int port, InetAddress localAddre
             return sslSocket;
         }
 
+        public void reload() {
+            final SSLSocketFactory newDelegate = delegateSupplier.get();
+            this.delegate = newDelegate;
+        }
+
         private void configureSSLSocket(SSLSocket socket) {
             SSLParameters parameters = new SSLParameters(ciphers, supportedProtocols);
             // we use the cipher suite order so that we can prefer the ciphers we set first in the list
@@ -533,12 +547,14 @@ final class SSLContextHolder {
         private final KeyConfig keyConfig;
         private final TrustConfig trustConfig;
         private final SSLConfiguration sslConfiguration;
+        private final List<Runnable> reloadListeners;
 
         SSLContextHolder(SSLContext context, SSLConfiguration sslConfiguration) {
             this.context = context;
             this.sslConfiguration = sslConfiguration;
             this.keyConfig = sslConfiguration.keyConfig();
             this.trustConfig = sslConfiguration.trustConfig();
+            this.reloadListeners = new ArrayList<>();
         }
 
         SSLContext sslContext() {
@@ -549,6 +565,7 @@ synchronized void reload() {
             invalidateSessions(context.getClientSessionContext());
             invalidateSessions(context.getServerSessionContext());
             reloadSslContext();
+            this.reloadListeners.forEach(Runnable::run);
         }
 
         private void reloadSslContext() {
@@ -582,6 +599,10 @@ X509ExtendedTrustManager getEmptyTrustManager() throws GeneralSecurityException,
             trustManagerFactory.init(keyStore);
             return (X509ExtendedTrustManager) trustManagerFactory.getTrustManagers()[0];
         }
+
+        public void addReloadListener(Runnable listener) {
+            this.reloadListeners.add(listener);
+        }
     }
 
     /**

x-pack/plugin/security/src/test/java/org/elasticsearch/xpack/security/authc/ldap/LdapSessionFactoryTests.java

@@ -14,18 +14,25 @@
 import org.elasticsearch.common.settings.Settings;
 import org.elasticsearch.common.util.concurrent.ThreadContext;
 import org.elasticsearch.common.util.concurrent.UncategorizedExecutionException;
+import org.elasticsearch.env.Environment;
 import org.elasticsearch.env.TestEnvironment;
 import org.elasticsearch.threadpool.TestThreadPool;
 import org.elasticsearch.threadpool.ThreadPool;
+import org.elasticsearch.watcher.ResourceWatcherService;
 import org.elasticsearch.xpack.core.security.authc.RealmConfig;
+import org.elasticsearch.xpack.core.security.authc.RealmSettings;
 import org.elasticsearch.xpack.core.security.authc.ldap.support.LdapSearchScope;
 import org.elasticsearch.xpack.core.security.authc.ldap.support.SessionFactorySettings;
+import org.elasticsearch.xpack.core.ssl.SSLConfigurationReloader;
 import org.elasticsearch.xpack.core.ssl.SSLService;
 import org.elasticsearch.xpack.security.authc.ldap.support.LdapSession;
 import org.elasticsearch.xpack.security.authc.ldap.support.LdapTestCase;
 import org.junit.After;
 import org.junit.Before;
 
+import java.nio.file.Files;
+import java.nio.file.Path;
+import java.nio.file.StandardCopyOption;
 import java.util.List;
 import java.util.concurrent.ExecutionException;
 
@@ -38,10 +45,23 @@ public class LdapSessionFactoryTests extends LdapTestCase {
     private Settings globalSettings;
     private SSLService sslService;
     private ThreadPool threadPool;
+    private Path ldapCaPath;
+
+    @Override
+    protected boolean openLdapsPort() {
+        // Support LDAPS, because it's used in some test
+        return true;
+    }
 
     @Before
     public void setup() throws Exception {
-        globalSettings = Settings.builder().put("path.home", createTempDir()).build();
+        final Path origCa = getDataPath("/org/elasticsearch/xpack/security/authc/ldap/support/ldap-ca.crt");
+        ldapCaPath = createTempFile();
+        Files.copy(origCa, ldapCaPath, StandardCopyOption.REPLACE_EXISTING);
+        globalSettings = Settings.builder()
+            .put("path.home", createTempDir())
+            .putList(RealmSettings.PREFIX + "ldap_realm.ssl.certificate_authorities", ldapCaPath.toString())
+            .build();
         sslService = new SSLService(globalSettings, TestEnvironment.newEnvironment(globalSettings));
         threadPool = new TestThreadPool("LdapSessionFactoryTests thread pool");
     }
@@ -53,7 +73,8 @@ public void shutdown() throws InterruptedException {
 
     public void testBindWithReadTimeout() throws Exception {
         InMemoryDirectoryServer ldapServer = randomFrom(ldapServers);
-        String ldapUrl = new LDAPURL("ldap", "localhost", ldapServer.getListenPort(), null, null, null, null).toString();
+        String protocol = randomFrom("ldap", "ldaps");
+        String ldapUrl = new LDAPURL(protocol, "localhost", ldapServer.getListenPort(protocol), null, null, null, null).toString();
         String groupSearchBase = "o=sevenSeas";
         String userTemplates = "cn={0},ou=people,o=sevenSeas";
 
@@ -187,4 +208,52 @@ public void testGroupLookupBase() throws Exception {
             assertThat(groups, contains("cn=HMS Lydia,ou=crews,ou=groups,o=sevenSeas"));
         }
     }
+
+    /**
+     * This test connects to the in memory LDAP server over SSL using 2 different CA certificates.
+     * One certificate is valid, the other is not.
+     * The path to the certificate never changes, but the contents are copied in place.
+     * If the realm's CA path is monitored for changes and the underlying SSL context is reloaded, then we will get two different outcomes
+     * (one failure, one success) depending on which file content is in place.
+     */
+    public void testSslTrustIsReloaded() throws Exception {
+        InMemoryDirectoryServer ldapServer = randomFrom(ldapServers);
+        String ldapUrl = new LDAPURL("ldaps", "localhost", ldapServer.getListenPort("ldaps"), null, null, null, null).toString();
+        String groupSearchBase = "o=sevenSeas";
+        String userTemplates = "cn={0},ou=people,o=sevenSeas";
+
+        Settings settings = Settings.builder()
+            .put(globalSettings)
+            .put(buildLdapSettings(ldapUrl, userTemplates, groupSearchBase, LdapSearchScope.SUB_TREE))
+            .build();
+
+        final Path realCa = getDataPath("/org/elasticsearch/xpack/security/authc/ldap/support/ldap-ca.crt");
+        final Path fakeCa = getDataPath("/org/elasticsearch/xpack/security/authc/ldap/support/smb_ca.crt");
+
+        final Environment environment = TestEnvironment.newEnvironment(settings);
+        RealmConfig config = new RealmConfig("ldap_realm", settings, globalSettings, environment, new ThreadContext(settings));
+        LdapSessionFactory sessionFactory = new LdapSessionFactory(config, sslService, threadPool);
+        String user = "Horatio Hornblower";
+        SecureString userPass = new SecureString("pass");
+
+        final ResourceWatcherService resourceWatcher = new ResourceWatcherService(settings, threadPool);
+        new SSLConfigurationReloader(environment, sslService, resourceWatcher);
+
+        Files.copy(fakeCa, ldapCaPath, StandardCopyOption.REPLACE_EXISTING);
+        resourceWatcher.notifyNow(ResourceWatcherService.Frequency.HIGH);
+
+        UncategorizedExecutionException e =
+            expectThrows(UncategorizedExecutionException.class, () -> session(sessionFactory, user, userPass));
+        assertThat(e.getCause(), instanceOf(ExecutionException.class));
+        assertThat(e.getCause().getCause(), instanceOf(LDAPException.class));
+        assertThat(e.getCause().getCause().getMessage(), containsString("SSLPeerUnverifiedException"));
+
+        Files.copy(realCa, ldapCaPath, StandardCopyOption.REPLACE_EXISTING);
+        resourceWatcher.notifyNow(ResourceWatcherService.Frequency.HIGH);
+
+        final LdapSession session = session(sessionFactory, user, userPass);
+        assertThat(session.userDn(), is("cn=Horatio Hornblower,ou=people,o=sevenSeas"));
+
+        session.close();
+    }
 }

x-pack/plugin/security/src/test/java/org/elasticsearch/xpack/security/authc/ldap/support/LdapTestCase.java

@@ -6,6 +6,8 @@
 package org.elasticsearch.xpack.security.authc.ldap.support;
 
 import com.unboundid.ldap.listener.InMemoryDirectoryServer;
+import com.unboundid.ldap.listener.InMemoryDirectoryServerConfig;
+import com.unboundid.ldap.listener.InMemoryListenerConfig;
 import com.unboundid.ldap.sdk.Attribute;
 import com.unboundid.ldap.sdk.LDAPConnection;
 import com.unboundid.ldap.sdk.LDAPConnectionPool;
@@ -29,13 +31,21 @@
 import org.elasticsearch.xpack.core.security.authc.ldap.support.LdapSearchScope;
 import org.elasticsearch.xpack.core.security.authc.ldap.support.SessionFactorySettings;
 import org.elasticsearch.xpack.core.security.authc.support.DnRoleMapperSettings;
+import org.elasticsearch.xpack.core.ssl.CertParsingUtils;
 import org.elasticsearch.xpack.core.ssl.VerificationMode;
 import org.elasticsearch.xpack.security.authc.support.DnRoleMapper;
 import org.junit.After;
 import org.junit.Before;
 import org.junit.BeforeClass;
 
+import javax.net.ssl.KeyManager;
+import javax.net.ssl.KeyManagerFactory;
+import javax.net.ssl.SSLContext;
+import javax.net.ssl.SSLServerSocketFactory;
+import javax.net.ssl.SSLSocketFactory;
+import javax.net.ssl.X509ExtendedKeyManager;
 import java.security.AccessController;
+import java.security.KeyStore;
 import java.security.PrivilegedAction;
 import java.security.PrivilegedExceptionAction;
 import java.util.ArrayList;
@@ -61,7 +71,25 @@ public static void setNumberOfLdapServers() {
     public void startLdap() throws Exception {
         ldapServers = new InMemoryDirectoryServer[numberOfLdapServers];
         for (int i = 0; i < numberOfLdapServers; i++) {
-            InMemoryDirectoryServer ldapServer = new InMemoryDirectoryServer("o=sevenSeas");
+            InMemoryDirectoryServerConfig serverConfig = new InMemoryDirectoryServerConfig("o=sevenSeas");
+            List<InMemoryListenerConfig> listeners = new ArrayList<>(2);
+            listeners.add(InMemoryListenerConfig.createLDAPConfig("ldap"));
+            if (openLdapsPort()) {
+                final char[] ldapPassword = "ldap-password".toCharArray();
+                final KeyStore ks = CertParsingUtils.getKeyStoreFromPEM(
+                    getDataPath("/org/elasticsearch/xpack/security/authc/ldap/support/ldap-test-case.crt"),
+                    getDataPath("/org/elasticsearch/xpack/security/authc/ldap/support/ldap-test-case.key"),
+                    ldapPassword
+                );
+                X509ExtendedKeyManager keyManager = CertParsingUtils.keyManager(ks, ldapPassword, KeyManagerFactory.getDefaultAlgorithm());
+                final SSLContext context = SSLContext.getInstance("TLSv1.2");
+                context.init(new KeyManager[] { keyManager }, null, null);
+                SSLServerSocketFactory serverSocketFactory = context.getServerSocketFactory();
+                SSLSocketFactory clientSocketFactory = context.getSocketFactory();
+                listeners.add(InMemoryListenerConfig.createLDAPSConfig("ldaps", null, 0, serverSocketFactory, clientSocketFactory));
+            }
+            serverConfig.setListenerConfigs(listeners);
+            InMemoryDirectoryServer ldapServer = new InMemoryDirectoryServer(serverConfig);
             ldapServer.add("o=sevenSeas", new Attribute("dc", "UnboundID"),
                     new Attribute("objectClass", "top", "domain", "extensibleObject"));
             ldapServer.importFromLDIF(false,
@@ -75,6 +103,10 @@ public void startLdap() throws Exception {
         }
     }
 
+    protected boolean openLdapsPort() {
+        return false;
+    }
+
     @After
     public void stopLdap() throws Exception {
         for (int i = 0; i < numberOfLdapServers; i++) {

x-pack/plugin/security/src/test/resources/org/elasticsearch/xpack/security/authc/ldap/support/ldap-ca.crt

@@ -0,0 +1,20 @@
+-----BEGIN CERTIFICATE-----
+MIIDSjCCAjKgAwIBAgIVAM5ozCjWHrKyM5Yf/WzUJg/ei3YMMA0GCSqGSIb3DQEB
+CwUAMDQxMjAwBgNVBAMTKUVsYXN0aWMgQ2VydGlmaWNhdGUgVG9vbCBBdXRvZ2Vu
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+ki54G/wfY7NoKhvWoj4zKbQg5lW5XADd2EFgoz9wkRrB2UzyuUYbBmJye/dnZnXn
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+2C5LrbRaaj1zECnwVmTnx1L9j/g7Ti83P+kdi7rI
+-----END CERTIFICATE-----

x-pack/plugin/security/src/test/resources/org/elasticsearch/xpack/security/authc/ldap/support/ldap-ca.key

@@ -0,0 +1,27 @@
+-----BEGIN RSA PRIVATE KEY-----
+MIIEpAIBAAKCAQEAt0KGY13TyMH2usvGHoakheMsXhVvpg0IurKDahiRowiY+yDe
+t9BnMeP+LJi99pi1ZOkcBsUueec/hT9xrfzS35jHOBlsAgJfpfrQIQT7jLQAmcDa
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+fWBoMPyScEkKk/43Te7VPvUm65h79R/1YDRL1zBKML8InKrcA7DT5iG6pe1Vc6CP
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+/gHCDOI0oh0Wu7j8/QtCxIO8+6GJyAOUE3f/amqpUa+U60mqPzS99A==
+-----END RSA PRIVATE KEY-----

x-pack/plugin/security/src/test/resources/org/elasticsearch/xpack/security/authc/ldap/support/ldap-test-case.crt

@@ -0,0 +1,20 @@
+-----BEGIN CERTIFICATE-----
+MIIDRTCCAi2gAwIBAgIVAJpxxIbXWyvdd6/rIFXPgWe6fyvTMA0GCSqGSIb3DQEB
+CwUAMDQxMjAwBgNVBAMTKUVsYXN0aWMgQ2VydGlmaWNhdGUgVG9vbCBBdXRvZ2Vu
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+XcCfGrZoJg9di1HbJrSJmv5QgRTM+/zkrA==
+-----END CERTIFICATE-----

x-pack/plugin/security/src/test/resources/org/elasticsearch/xpack/security/authc/ldap/support/ldap-test-case.key

@@ -0,0 +1,30 @@
+-----BEGIN RSA PRIVATE KEY-----
+Proc-Type: 4,ENCRYPTED
+DEK-Info: DES-EDE3-CBC,F7442C1F07A3A829
+
+jIINPsJbBILgZPf/MXVO5FPESwscOXnP9hQ6RpiQnxs3OlFWHqcuc0xw8jUeTGkS
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+yr/ZzeN3iAECK6rYnG+GGePN4iyBncBHGztbGzjcmPujbMQ96bpWAChNngOR9TUx
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+-----END RSA PRIVATE KEY-----