Fix bug in webserver start when loading PKCS#11 KeyStore

See gh-32179

spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/jetty/SslServerCustomizer.java

@@ -19,6 +19,7 @@ package org.springframework.boot.web.embedded.jetty;
 import java.io.IOException;
 import java.net.InetSocketAddress;
 import java.net.URL;
+import java.util.Objects;
 
 import org.eclipse.jetty.alpn.server.ALPNServerConnectionFactory;
 import org.eclipse.jetty.http.HttpVersion;
@@ -51,6 +52,7 @@ import org.springframework.util.ResourceUtils;
  * @author Brian Clozel
  * @author Olivier Lamy
  * @author Chris Bono
+ * @author Cyril Dangerville
  */
 class SslServerCustomizer implements JettyServerCustomizer {
 
@@ -220,16 +222,25 @@ class SslServerCustomizer implements JettyServerCustomizer {
 	}
 
 	private void configureSslKeyStore(SslContextFactory.Server factory, Ssl ssl) {
-		try {
-			URL url = ResourceUtils.getURL(ssl.getKeyStore());
-			factory.setKeyStoreResource(Resource.newResource(url));
+		final String keystoreType = Objects.requireNonNullElse(ssl.getKeyStoreType(), "JKS");
+		final String keystoreLocation = ssl.getKeyStore();
+		if (keystoreType.equalsIgnoreCase("PKCS11")) {
+			if (keystoreLocation != null && !keystoreLocation.isBlank()) {
+				throw new IllegalArgumentException("Input keystore location is not valid for keystore type 'PKCS11': '"
+						+ keystoreLocation + "'. Must be undefined / null.");
+			}
 		}
-		catch (Exception ex) {
-			throw new WebServerException("Could not load key store '" + ssl.getKeyStore() + "'", ex);
-		}
-		if (ssl.getKeyStoreType() != null) {
-			factory.setKeyStoreType(ssl.getKeyStoreType());
+		else {
+			try {
+				URL url = ResourceUtils.getURL(keystoreLocation);
+				factory.setKeyStoreResource(Resource.newResource(url));
+			}
+			catch (Exception ex) {
+				throw new WebServerException("Could not load key store '" + keystoreLocation + "'", ex);
+			}
 		}
+
+		factory.setKeyStoreType(keystoreType);
 		if (ssl.getKeyStoreProvider() != null) {
 			factory.setKeyStoreProvider(ssl.getKeyStoreProvider());
 		}

spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/netty/SslServerCustomizer.java

@@ -57,6 +57,7 @@ import org.springframework.util.ResourceUtils;
  * @author Brian Clozel
  * @author Raheela Aslam
  * @author Chris Bono
+ * @author Cyril Dangerville
  * @since 2.0.0
  * @deprecated this class is meant for Spring Boot internal use only.
  */
@@ -171,17 +172,27 @@ public class SslServerCustomizer implements NettyServerCustomizer {
 	private KeyStore loadStore(String type, String provider, String resource, String password) throws Exception {
 		type = (type != null) ? type : "JKS";
 		KeyStore store = (provider != null) ? KeyStore.getInstance(type, provider) : KeyStore.getInstance(type);
-		try {
-			URL url = ResourceUtils.getURL(resource);
-			try (InputStream stream = url.openStream()) {
-				store.load(stream, (password != null) ? password.toCharArray() : null);
+		if (type.equalsIgnoreCase("PKCS11")) {
+			if (resource != null && !resource.isBlank()) {
+				throw new IllegalArgumentException("Input keystore location is not valid for keystore type 'PKCS11': '"
+						+ resource + "'. Must be undefined / null.");
 			}
-			return store;
+
+			store.load(null, (password != null) ? password.toCharArray() : null);
 		}
-		catch (Exception ex) {
-			throw new WebServerException("Could not load key store '" + resource + "'", ex);
+		else {
+			try {
+				URL url = ResourceUtils.getURL(resource);
+				try (InputStream stream = url.openStream()) {
+					store.load(stream, (password != null) ? password.toCharArray() : null);
+				}
+			}
+			catch (Exception ex) {
+				throw new WebServerException("Could not load key store '" + resource + "'", ex);
+			}
 		}
 
+		return store;
 	}
 
 	/**

spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/tomcat/SslConnectorCustomizer.java

@@ -17,6 +17,7 @@
 package org.springframework.boot.web.embedded.tomcat;
 
 import java.io.FileNotFoundException;
+import java.util.Objects;
 
 import org.apache.catalina.connector.Connector;
 import org.apache.coyote.ProtocolHandler;
@@ -39,6 +40,7 @@ import org.springframework.util.StringUtils;
  * @author Brian Clozel
  * @author Andy Wilkinson
  * @author Scott Frederick
+ * @author Cyril Dangerville
  */
 class SslConnectorCustomizer implements TomcatConnectorCustomizer {
 
@@ -139,15 +141,24 @@ class SslConnectorCustomizer implements TomcatConnectorCustomizer {
 	}
 
 	private void configureSslKeyStore(SSLHostConfigCertificate certificate, Ssl ssl) {
-		try {
-			certificate.setCertificateKeystoreFile(ResourceUtils.getURL(ssl.getKeyStore()).toString());
+		final String keystoreType = Objects.requireNonNullElse(ssl.getKeyStoreType(), "JKS");
+		final String keystoreLocation = ssl.getKeyStore();
+		if (keystoreType.equalsIgnoreCase("PKCS11")) {
+			if (keystoreLocation != null && !keystoreLocation.isBlank()) {
+				throw new IllegalArgumentException("Input keystore location is not valid for keystore type 'PKCS11': '"
+						+ keystoreLocation + "'. Must be undefined / null.");
+			}
 		}
-		catch (Exception ex) {
-			throw new WebServerException("Could not load key store '" + ssl.getKeyStore() + "'", ex);
-		}
-		if (ssl.getKeyStoreType() != null) {
-			certificate.setCertificateKeystoreType(ssl.getKeyStoreType());
+		else {
+			try {
+				certificate.setCertificateKeystoreFile(ResourceUtils.getURL(keystoreLocation).toString());
+			}
+			catch (Exception ex) {
+				throw new WebServerException("Could not load key store '" + keystoreLocation + "'", ex);
+			}
 		}
+
+		certificate.setCertificateKeystoreType(keystoreType);
 		if (ssl.getKeyStoreProvider() != null) {
 			certificate.setCertificateKeystoreProvider(ssl.getKeyStoreProvider());
 		}

spring-boot-project/spring-boot/src/main/java/org/springframework/boot/web/embedded/undertow/SslBuilderCustomizer.java

@@ -51,6 +51,7 @@ import org.springframework.util.ResourceUtils;
  *
  * @author Brian Clozel
  * @author Raheela Aslam
+ * @author Cyril Dangerville
  */
 class SslBuilderCustomizer implements UndertowBuilderCustomizer {
 
@@ -180,16 +181,27 @@ class SslBuilderCustomizer implements UndertowBuilderCustomizer {
 	private KeyStore loadStore(String type, String provider, String resource, String password) throws Exception {
 		type = (type != null) ? type : "JKS";
 		KeyStore store = (provider != null) ? KeyStore.getInstance(type, provider) : KeyStore.getInstance(type);
-		try {
-			URL url = ResourceUtils.getURL(resource);
-			try (InputStream stream = url.openStream()) {
-				store.load(stream, (password != null) ? password.toCharArray() : null);
+		if (type.equalsIgnoreCase("PKCS11")) {
+			if (resource != null && !resource.isBlank()) {
+				throw new IllegalArgumentException("Input keystore location is not valid for keystore type 'PKCS11': '"
+						+ resource + "'. Must be undefined / null.");
 			}
-			return store;
+
+			store.load(null, (password != null) ? password.toCharArray() : null);
 		}
-		catch (Exception ex) {
-			throw new WebServerException("Could not load key store '" + resource + "'", ex);
+		else {
+			try {
+				URL url = ResourceUtils.getURL(resource);
+				try (InputStream stream = url.openStream()) {
+					store.load(stream, (password != null) ? password.toCharArray() : null);
+				}
+			}
+			catch (Exception ex) {
+				throw new WebServerException("Could not load key store '" + resource + "'", ex);
+			}
 		}
+
+		return store;
 	}
 
 	/**

spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/embedded/jetty/SslServerCustomizerTests.java

@@ -17,6 +17,8 @@
 package org.springframework.boot.web.embedded.jetty;
 
 import java.net.InetSocketAddress;
+import java.security.Provider;
+import java.security.Security;
 import java.util.ArrayList;
 import java.util.List;
 
@@ -27,24 +29,47 @@ import org.eclipse.jetty.server.HttpConnectionFactory;
 import org.eclipse.jetty.server.Server;
 import org.eclipse.jetty.server.SslConnectionFactory;
 import org.eclipse.jetty.util.ssl.SslContextFactory;
+import org.junit.jupiter.api.AfterAll;
+import org.junit.jupiter.api.BeforeAll;
 import org.junit.jupiter.api.Test;
 import org.junit.jupiter.api.condition.OS;
 
 import org.springframework.boot.testsupport.junit.DisabledOnOs;
+import org.springframework.boot.web.embedded.netty.MockPkcs11SecurityProvider;
 import org.springframework.boot.web.server.Http2;
 import org.springframework.boot.web.server.Ssl;
 import org.springframework.boot.web.server.WebServerException;
 
 import static org.assertj.core.api.Assertions.assertThat;
 import static org.assertj.core.api.Assertions.assertThatExceptionOfType;
+import static org.assertj.core.api.Assertions.assertThatIllegalArgumentException;
+import static org.assertj.core.api.Assertions.assertThatNoException;
 
 /**
  * Tests for {@link SslServerCustomizer}.
  *
  * @author Andy Wilkinson
+ * @author Cyril Dangerville
  */
 class SslServerCustomizerTests {
 
+	private static final Provider PKCS11_PROVIDER = new MockPkcs11SecurityProvider();
+
+	@BeforeAll
+	static void beforeAllTests() {
+		/*
+		 * Add the mock Java security provider for PKCS#11-related unit tests.
+		 *
+		 */
+		Security.addProvider(PKCS11_PROVIDER);
+	}
+
+	@AfterAll
+	static void afterAllTests() {
+		// Remove the provider previously added in setup()
+		Security.removeProvider(PKCS11_PROVIDER.getName());
+	}
+
 	@Test
 	@SuppressWarnings("rawtypes")
 	void whenHttp2IsNotEnabledServerConnectorHasSslAndHttpConnectionFactories() {
@@ -82,8 +107,11 @@ class SslServerCustomizerTests {
 		assertThat(((ALPNServerConnectionFactory) factories.get(1)).getDefaultProtocol()).isNull();
 	}
 
+	/**
+	 * Null/undefined keystore is invalid unless keystore type is PKCS11.
+	 */
 	@Test
-	void configureSslWhenSslIsEnabledWithNoKeyStoreThrowsWebServerException() {
+	void configureSslWhenSslIsEnabledWithNoKeyStoreAndNotPkcs11ThrowsWebServerException() {
 		Ssl ssl = new Ssl();
 		SslServerCustomizer customizer = new SslServerCustomizer(null, ssl, null, null);
 		assertThatExceptionOfType(Exception.class)
@@ -94,6 +122,33 @@ class SslServerCustomizerTests {
 				});
 	}
 
+	/**
+	 * No keystore path should be defined if keystore type is PKCS#11.
+	 */
+	@Test
+	void configureSslWhenSslIsEnabledWithPkcs11AndKeyStoreThrowsIllegalArgumentException() {
+		Ssl ssl = new Ssl();
+		ssl.setKeyStoreType("PKCS11");
+		ssl.setKeyStoreProvider(PKCS11_PROVIDER.getName());
+		ssl.setKeyStore("src/test/resources/test.jks");
+		ssl.setKeyPassword("password");
+		SslServerCustomizer customizer = new SslServerCustomizer(null, ssl, null, null);
+		assertThatIllegalArgumentException()
+				.isThrownBy(() -> customizer.configureSsl(new SslContextFactory.Server(), ssl, null))
+				.withMessageContaining("Input keystore location is not valid for keystore type 'PKCS11'");
+	}
+
+	@Test
+	void customizeWhenSslIsEnabledWithPkcs11AndKeyStoreProvider() {
+		Ssl ssl = new Ssl();
+		ssl.setKeyStoreType("PKCS11");
+		ssl.setKeyStoreProvider(PKCS11_PROVIDER.getName());
+		ssl.setKeyStorePassword("1234");
+		SslServerCustomizer customizer = new SslServerCustomizer(null, ssl, null, null);
+		// Loading the KeyManagerFactory should be successful
+		assertThatNoException().isThrownBy(() -> customizer.configureSsl(new SslContextFactory.Server(), ssl, null));
+	}
+
 	private Server createCustomizedServer() {
 		return createCustomizedServer(new Http2());
 	}

spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/embedded/netty/MockKeyStoreSpi.java

@@ -0,0 +1,139 @@
+/*
+ * Copyright 2012-2022 the original author or authors.
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ *
+ *      https://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+package org.springframework.boot.web.embedded.netty;
+
+import java.io.InputStream;
+import java.io.OutputStream;
+import java.security.Key;
+import java.security.KeyPair;
+import java.security.KeyPairGenerator;
+import java.security.KeyStoreSpi;
+import java.security.NoSuchAlgorithmException;
+import java.security.cert.Certificate;
+import java.util.Collections;
+import java.util.Date;
+import java.util.Enumeration;
+import java.util.HashMap;
+import java.util.Map;
+
+/**
+ * Mock Security Provider for testing purposes only (e.g. SslServerCustomizerTests class)
+ *
+ * @author Cyril Dangerville
+ */
+public class MockKeyStoreSpi extends KeyStoreSpi {
+
+	private static final KeyPairGenerator KEYGEN;
+
+	static {
+		try {
+			KEYGEN = KeyPairGenerator.getInstance("RSA");
+			KEYGEN.initialize(2048);
+		}
+		catch (NoSuchAlgorithmException ex) {
+			throw new RuntimeException(ex);
+		}
+	}
+
+	private final Map<String, KeyPair> aliases = new HashMap<>();
+
+	@Override
+	public Key engineGetKey(String alias, char[] password) {
+		final KeyPair keyPair = this.aliases.get(alias);
+		return (keyPair != null) ? keyPair.getPrivate() : null;
+	}
+
+	@Override
+	public Certificate[] engineGetCertificateChain(String alias) {
+		return new Certificate[0];
+	}
+
+	@Override
+	public Certificate engineGetCertificate(String alias) {
+		throw new UnsupportedOperationException();
+	}
+
+	@Override
+	public Date engineGetCreationDate(String alias) {
+		throw new UnsupportedOperationException();
+	}
+
+	@Override
+	public void engineSetKeyEntry(String alias, Key key, char[] password, Certificate[] chain) {
+		throw new UnsupportedOperationException();
+	}
+
+	@Override
+	public void engineSetKeyEntry(String alias, byte[] key, Certificate[] chain) {
+		throw new UnsupportedOperationException();
+	}
+
+	@Override
+	public void engineSetCertificateEntry(String alias, Certificate cert) {
+		throw new UnsupportedOperationException();
+	}
+
+	@Override
+	public void engineDeleteEntry(String alias) {
+		throw new UnsupportedOperationException();
+	}
+
+	@Override
+	public Enumeration<String> engineAliases() {
+		return Collections.enumeration(this.aliases.keySet());
+	}
+
+	@Override
+	public boolean engineContainsAlias(String alias) {
+		// contains any required alias, for testing purposes
+		// Add alias to aliases list on the fly
+		this.aliases.put(alias, KEYGEN.generateKeyPair());
+		return true;
+	}
+
+	@Override
+	public int engineSize() {
+		throw new UnsupportedOperationException();
+	}
+
+	@Override
+	public boolean engineIsKeyEntry(String alias) {
+		// Handle all keystore entries as key entries
+		return this.aliases.containsKey(alias);
+	}
+
+	@Override
+	public boolean engineIsCertificateEntry(String alias) {
+		return false;
+	}
+
+	@Override
+	public String engineGetCertificateAlias(Certificate cert) {
+		throw new UnsupportedOperationException();
+	}
+
+	@Override
+	public void engineStore(OutputStream stream, char[] password) {
+		throw new UnsupportedOperationException();
+	}
+
+	@Override
+	public void engineLoad(InputStream stream, char[] password) {
+		// Nothing to do, this is a mock keystore implementation, for testing only.
+	}
+
+}

spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/embedded/netty/MockPkcs11SecurityProvider.java

@@ -0,0 +1,48 @@
+/*
+ * Copyright 2012-2022 the original author or authors.
+ *
+ * Licensed under the Apache License, Version 2.0 (the "License");
+ * you may not use this file except in compliance with the License.
+ * You may obtain a copy of the License at
+ *
+ *      https://www.apache.org/licenses/LICENSE-2.0
+ *
+ * Unless required by applicable law or agreed to in writing, software
+ * distributed under the License is distributed on an "AS IS" BASIS,
+ * WITHOUT WARRANTIES OR CONDITIONS OF ANY KIND, either express or implied.
+ * See the License for the specific language governing permissions and
+ * limitations under the License.
+ */
+
+package org.springframework.boot.web.embedded.netty;
+
+import java.security.KeyStoreSpi;
+import java.security.Provider;
+
+/**
+ * Mock PKCS#11 Security Provider for testing purposes only (e.g. SslServerCustomizerTests
+ * class)
+ *
+ * @author Cyril Dangerville
+ */
+public class MockPkcs11SecurityProvider extends Provider {
+
+	private static final String DEFAULT_PROVIDER_NAME = "Mock-PKCS11";
+
+	private static final String VERSION = "0.1";
+
+	private static final String DESCRIPTION = "Mock PKCS11 Provider";
+
+	/**
+	 * Create Security Provider named {@value #DEFAULT_PROVIDER_NAME}, version
+	 * {@value #VERSION} and providing PKCS11 KeyStores with {@link MockKeyStoreSpi} as
+	 * {@link KeyStoreSpi} implementation.
+	 */
+	public MockPkcs11SecurityProvider() {
+		super(DEFAULT_PROVIDER_NAME, VERSION, DESCRIPTION);
+
+		putService(new Service(this, "KeyStore", "PKCS11",
+				"org.springframework.boot.web.embedded.netty.MockKeyStoreSpi", null, null));
+	}
+
+}

spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/embedded/netty/SslServerCustomizerTests.java

@@ -17,23 +17,50 @@
 package org.springframework.boot.web.embedded.netty;
 
 import java.security.NoSuchProviderException;
+import java.security.Provider;
+import java.security.Security;
 
+import org.junit.jupiter.api.AfterAll;
+import org.junit.jupiter.api.BeforeAll;
 import org.junit.jupiter.api.Test;
 
 import org.springframework.boot.web.server.Ssl;
 import org.springframework.boot.web.server.WebServerException;
 
 import static org.assertj.core.api.Assertions.assertThatIllegalStateException;
+import static org.assertj.core.api.Assertions.assertThatNoException;
 
 /**
  * Tests for {@link SslServerCustomizer}.
  *
  * @author Andy Wilkinson
  * @author Raheela Aslam
+ * @author Cyril Dangerville
  */
 @SuppressWarnings("deprecation")
 class SslServerCustomizerTests {
 
+	private static final Provider PKCS11_PROVIDER = new MockPkcs11SecurityProvider();
+
+	@BeforeAll
+	static void setup() {
+		/*
+		 * Add the mock Java security provider for PKCS#11-related unit tests.
+		 *
+		 * For an integration test with an actual PKCS#11 library - SoftHSM - properly
+		 * installed and configured on the system (inside a container), used via Java
+		 * built-in SunPKCS11 provider, see the 'spring-boot-smoke-test-webflux-ssl'
+		 * project in 'spring-boot-tests/spring-boot-smoke-tests' folder.
+		 */
+		Security.addProvider(PKCS11_PROVIDER);
+	}
+
+	@AfterAll
+	static void shutdown() {
+		// Remove the provider previously added in setup()
+		Security.removeProvider(PKCS11_PROVIDER.getName());
+	}
+
 	@Test
 	void keyStoreProviderIsUsedWhenCreatingKeyStore() {
 		Ssl ssl = new Ssl();
@@ -58,12 +85,42 @@ class SslServerCustomizerTests {
 				.withMessageContaining("com.example.TrustStoreProvider");
 	}
 
+	/**
+	 * Null/undefined keystore is not valid unless keystore type is PKCS11.
+	 */
 	@Test
-	void getKeyManagerFactoryWhenSslIsEnabledWithNoKeyStoreThrowsWebServerException() {
+	void getKeyManagerFactoryWhenSslIsEnabledWithNoKeyStoreAndNotPkcs11ThrowsWebServerException() {
 		Ssl ssl = new Ssl();
 		SslServerCustomizer customizer = new SslServerCustomizer(ssl, null, null);
 		assertThatIllegalStateException().isThrownBy(() -> customizer.getKeyManagerFactory(ssl, null))
 				.withCauseInstanceOf(WebServerException.class).withMessageContaining("Could not load key store 'null'");
 	}
 
+	/**
+	 * No keystore path should be defined if keystore type is PKCS#11.
+	 */
+	@Test
+	void getKeyManagerFactoryWhenSslIsEnabledWithPkcs11AndKeyStoreThrowsIllegalArgumentException() {
+		Ssl ssl = new Ssl();
+		ssl.setKeyStoreType("PKCS11");
+		ssl.setKeyStoreProvider(PKCS11_PROVIDER.getName());
+		ssl.setKeyStore("src/test/resources/test.jks");
+		ssl.setKeyPassword("password");
+		SslServerCustomizer customizer = new SslServerCustomizer(ssl, null, null);
+		assertThatIllegalStateException().isThrownBy(() -> customizer.getKeyManagerFactory(ssl, null))
+				.withCauseInstanceOf(IllegalArgumentException.class)
+				.withMessageContaining("Input keystore location is not valid for keystore type 'PKCS11'");
+	}
+
+	@Test
+	void getKeyManagerFactoryWhenSslIsEnabledWithPkcs11AndKeyStoreProvider() {
+		Ssl ssl = new Ssl();
+		ssl.setKeyStoreType("PKCS11");
+		ssl.setKeyStoreProvider(PKCS11_PROVIDER.getName());
+		ssl.setKeyStorePassword("1234");
+		SslServerCustomizer customizer = new SslServerCustomizer(ssl, null, null);
+		// Loading the KeyManagerFactory should be successful
+		assertThatNoException().isThrownBy(() -> customizer.getKeyManagerFactory(ssl, null));
+	}
+
 }

spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/embedded/tomcat/SslConnectorCustomizerTests.java

@@ -21,6 +21,8 @@ import java.io.InputStream;
 import java.security.KeyStore;
 import java.security.KeyStoreException;
 import java.security.NoSuchAlgorithmException;
+import java.security.Provider;
+import java.security.Security;
 import java.security.cert.CertificateException;
 import java.util.Set;
 
@@ -29,13 +31,16 @@ import org.apache.catalina.connector.Connector;
 import org.apache.catalina.startup.Tomcat;
 import org.apache.tomcat.util.net.SSLHostConfig;
 import org.apache.tomcat.util.net.SSLHostConfigCertificate;
+import org.junit.jupiter.api.AfterAll;
 import org.junit.jupiter.api.AfterEach;
+import org.junit.jupiter.api.BeforeAll;
 import org.junit.jupiter.api.BeforeEach;
 import org.junit.jupiter.api.Test;
 import org.junit.jupiter.api.extension.ExtendWith;
 
 import org.springframework.boot.testsupport.system.CapturedOutput;
 import org.springframework.boot.testsupport.system.OutputCaptureExtension;
+import org.springframework.boot.web.embedded.netty.MockPkcs11SecurityProvider;
 import org.springframework.boot.testsupport.web.servlet.DirtiesUrlFactories;
 import org.springframework.boot.web.server.Ssl;
 import org.springframework.boot.web.server.SslStoreProvider;
@@ -45,6 +50,8 @@ import org.springframework.core.io.Resource;
 
 import static org.assertj.core.api.Assertions.assertThat;
 import static org.assertj.core.api.Assertions.assertThatExceptionOfType;
+import static org.assertj.core.api.Assertions.assertThatIllegalArgumentException;
+import static org.assertj.core.api.Assertions.assertThatNoException;
 import static org.mockito.BDDMockito.given;
 import static org.mockito.Mockito.mock;
 
@@ -54,15 +61,33 @@ import static org.mockito.Mockito.mock;
  * @author Brian Clozel
  * @author Andy Wilkinson
  * @author Scott Frederick
+ * @author Cyril Dangerville
  */
 @ExtendWith(OutputCaptureExtension.class)
 @DirtiesUrlFactories
 class SslConnectorCustomizerTests {
 
+	private static final Provider PKCS11_PROVIDER = new MockPkcs11SecurityProvider();
+
 	private Tomcat tomcat;
 
 	private Connector connector;
 
+	@BeforeAll
+	static void beforeAllTests() {
+		/*
+		 * Add the mock Java security provider for PKCS#11-related unit tests.
+		 *
+		 */
+		Security.addProvider(PKCS11_PROVIDER);
+	}
+
+	@AfterAll
+	static void afterAllTests() {
+		// Remove the provider previously added in setup()
+		Security.removeProvider(PKCS11_PROVIDER.getName());
+	}
+
 	@BeforeEach
 	void setup() {
 		this.tomcat = new Tomcat();
@@ -176,13 +201,42 @@ class SslConnectorCustomizerTests {
 		assertThat(output).doesNotContain("Password verification failed");
 	}
 
+	/**
+	 * Null/undefined keystore is invalid unless keystore type is PKCS11.
+	 */
 	@Test
-	void customizeWhenSslIsEnabledWithNoKeyStoreThrowsWebServerException() {
+	void customizeWhenSslIsEnabledWithNoKeyStoreAndNotPkcs11ThrowsWebServerException() {
 		assertThatExceptionOfType(WebServerException.class)
 				.isThrownBy(() -> new SslConnectorCustomizer(new Ssl(), null).customize(this.tomcat.getConnector()))
 				.withMessageContaining("Could not load key store 'null'");
 	}
 
+	/**
+	 * No keystore path should be defined if keystore type is PKCS#11.
+	 */
+	@Test
+	void customizeWhenSslIsEnabledWithPkcs11AndKeyStoreThrowsIllegalArgumentException() {
+		Ssl ssl = new Ssl();
+		ssl.setKeyStoreType("PKCS11");
+		ssl.setKeyStoreProvider(PKCS11_PROVIDER.getName());
+		ssl.setKeyStore("src/test/resources/test.jks");
+		ssl.setKeyPassword("password");
+		SslConnectorCustomizer customizer = new SslConnectorCustomizer(ssl, null);
+		assertThatIllegalArgumentException().isThrownBy(() -> customizer.customize(this.tomcat.getConnector()))
+				.withMessageContaining("Input keystore location is not valid for keystore type 'PKCS11'");
+	}
+
+	@Test
+	void customizeWhenSslIsEnabledWithPkcs11AndKeyStoreProvider() {
+		Ssl ssl = new Ssl();
+		ssl.setKeyStoreType("PKCS11");
+		ssl.setKeyStoreProvider(PKCS11_PROVIDER.getName());
+		ssl.setKeyStorePassword("1234");
+		SslConnectorCustomizer customizer = new SslConnectorCustomizer(ssl, null);
+		// Loading the KeyManagerFactory should be successful
+		assertThatNoException().isThrownBy(() -> customizer.customize(this.tomcat.getConnector()));
+	}
+
 	private KeyStore loadStore() throws KeyStoreException, IOException, NoSuchAlgorithmException, CertificateException {
 		KeyStore keyStore = KeyStore.getInstance("JKS");
 		Resource resource = new ClassPathResource("test.jks");

spring-boot-project/spring-boot/src/test/java/org/springframework/boot/web/embedded/undertow/SslBuilderCustomizerTests.java

@@ -18,26 +18,50 @@ package org.springframework.boot.web.embedded.undertow;
 
 import java.net.InetAddress;
 import java.security.NoSuchProviderException;
+import java.security.Provider;
+import java.security.Security;
 
 import javax.net.ssl.KeyManager;
 
+import org.junit.jupiter.api.AfterAll;
+import org.junit.jupiter.api.BeforeAll;
 import org.junit.jupiter.api.Test;
 
+import org.springframework.boot.web.embedded.netty.MockPkcs11SecurityProvider;
 import org.springframework.boot.web.server.Ssl;
 import org.springframework.boot.web.server.WebServerException;
 import org.springframework.test.util.ReflectionTestUtils;
 
 import static org.assertj.core.api.Assertions.assertThat;
 import static org.assertj.core.api.Assertions.assertThatIllegalStateException;
+import static org.assertj.core.api.Assertions.assertThatNoException;
 
 /**
  * Tests for {@link SslBuilderCustomizer}
  *
  * @author Brian Clozel
  * @author Raheela Aslam
+ * @author Cyril Dangerville
  */
 class SslBuilderCustomizerTests {
 
+	private static final Provider PKCS11_PROVIDER = new MockPkcs11SecurityProvider();
+
+	@BeforeAll
+	static void beforeAllTests() {
+		/*
+		 * Add the mock Java security provider for PKCS#11-related unit tests.
+		 *
+		 */
+		Security.addProvider(PKCS11_PROVIDER);
+	}
+
+	@AfterAll
+	static void afterAllTests() {
+		// Remove the provider previously added in setup()
+		Security.removeProvider(PKCS11_PROVIDER.getName());
+	}
+
 	@Test
 	void getKeyManagersWhenAliasIsNullShouldNotDecorate() throws Exception {
 		Ssl ssl = new Ssl();
@@ -76,8 +100,11 @@ class SslBuilderCustomizerTests {
 				.withMessageContaining("com.example.TrustStoreProvider");
 	}
 
+	/**
+	 * Null/undefined keystore is invalid unless keystore type is PKCS11.
+	 */
 	@Test
-	void getKeyManagersWhenSslIsEnabledWithNoKeyStoreThrowsWebServerException() throws Exception {
+	void getKeyManagersWhenSslIsEnabledWithNoKeyStoreAndNotPkcs11ThrowsWebServerException() throws Exception {
 		Ssl ssl = new Ssl();
 		SslBuilderCustomizer customizer = new SslBuilderCustomizer(8080, InetAddress.getLocalHost(), ssl, null);
 		assertThatIllegalStateException()
@@ -85,4 +112,33 @@ class SslBuilderCustomizerTests {
 				.withCauseInstanceOf(WebServerException.class).withMessageContaining("Could not load key store 'null'");
 	}
 
+	/**
+	 * No keystore path should be defined if keystore type is PKCS#11.
+	 */
+	@Test
+	void configureSslWhenSslIsEnabledWithPkcs11AndKeyStoreThrowsIllegalArgumentException() throws Exception {
+		Ssl ssl = new Ssl();
+		ssl.setKeyStoreType("PKCS11");
+		ssl.setKeyStoreProvider(PKCS11_PROVIDER.getName());
+		ssl.setKeyStore("src/test/resources/test.jks");
+		ssl.setKeyPassword("password");
+		SslBuilderCustomizer customizer = new SslBuilderCustomizer(8080, InetAddress.getLocalHost(), ssl, null);
+		assertThatIllegalStateException()
+				.isThrownBy(() -> ReflectionTestUtils.invokeMethod(customizer, "getKeyManagers", ssl, null))
+				.withCauseInstanceOf(IllegalArgumentException.class)
+				.withMessageContaining("Input keystore location is not valid for keystore type 'PKCS11'");
+	}
+
+	@Test
+	void customizeWhenSslIsEnabledWithPkcs11AndKeyStoreProvider() throws Exception {
+		Ssl ssl = new Ssl();
+		ssl.setKeyStoreType("PKCS11");
+		ssl.setKeyStoreProvider(PKCS11_PROVIDER.getName());
+		ssl.setKeyStorePassword("1234");
+		SslBuilderCustomizer customizer = new SslBuilderCustomizer(8080, InetAddress.getLocalHost(), ssl, null);
+		// Loading the KeyManagerFactory should be successful
+		assertThatNoException()
+				.isThrownBy(() -> ReflectionTestUtils.invokeMethod(customizer, "getKeyManagers", ssl, null));
+	}
+
 }