Add support for encrypted PKCS#8

Add support for encrypted PEM file (encrypted PKCS#8) to the TLS registry. This is invisible for the extensions, the key being decrypted and passed unencrypted to the extensions (the unencrypted key is never written on disk).

Fix quarkusio#44262

bom/application/pom.xml

@@ -337,6 +337,12 @@
                 <version>${smallrye-certificate-generator.version}</version>
             </dependency>
 
+            <dependency>
+                <groupId>io.smallrye.certs</groupId>
+                <artifactId>smallrye-private-key-pem-parser</artifactId>
+                <version>${smallrye-certificate-generator.version}</version>
+            </dependency>
+
             <!-- Jackson dependencies, imported as a BOM -->
             <dependency>
                 <groupId>com.fasterxml.jackson</groupId>

docs/src/main/asciidoc/tls-registry-reference.adoc

@@ -228,6 +228,21 @@ For example, `quarkus.tls.key-store.pem.order=b,c,a`.
 This setting is important when using SNI, because it uses the first specified pair as the default.
 ====
 
+When using PEM keystore, the following formats are supported:
+
+- PKCS#8 private key (unencrypted)
+- PKCS#1 RSA private key (unencrypted)
+- Encrypted PKCS#8 private key (encrypted with AES-128-CBC)
+
+In the later case, the `quarkus.tls.key-store.pem.password` (or `quarkus.tls.key-store.pem.<name>.password`) property must be set to the password used to decrypt the private key:
+
+[source,properties]
+----
+quarkus.tls.http.key-store.pem.cert=certificate.crt
+quarkus.tls.http.key-store.pem.key=key.key
+quarkus.tls.http.key-store.pem.password=password
+----
+
 ==== PKCS12 keystores
 
 PKCS12 keystores are single files that contain the certificate and the private key.

extensions/tls-registry/cli/src/main/java/io/quarkus/tls/cli/letsencrypt/LetsEncryptHelpers.java

@@ -44,7 +44,7 @@ public static void writePrivateKeyAndCertificateChainsAsPem(PrivateKey pk, X509C
             throw new IllegalArgumentException("The certificate chain cannot be null or empty");
         }
 
-        CertificateUtils.writePrivateKeyToPem(pk, privateKeyFile);
+        CertificateUtils.writePrivateKeyToPem(pk, null, privateKeyFile);
 
         if (chain.length == 1) {
             CertificateUtils.writeCertificateToPEM(chain[0], certificateChainFile);

extensions/tls-registry/deployment/src/test/java/io/quarkus/tls/DefaultEncryptedPemKeyStoreTest.java

@@ -0,0 +1,58 @@
+package io.quarkus.tls;
+
+import static org.assertj.core.api.Assertions.assertThat;
+
+import java.security.KeyStoreException;
+import java.security.cert.CertificateParsingException;
+import java.security.cert.X509Certificate;
+
+import jakarta.inject.Inject;
+
+import org.jboss.shrinkwrap.api.ShrinkWrap;
+import org.jboss.shrinkwrap.api.asset.StringAsset;
+import org.jboss.shrinkwrap.api.spec.JavaArchive;
+import org.junit.jupiter.api.Test;
+import org.junit.jupiter.api.extension.RegisterExtension;
+
+import io.quarkus.test.QuarkusUnitTest;
+import io.smallrye.certs.Format;
+import io.smallrye.certs.junit5.Certificate;
+import io.smallrye.certs.junit5.Certificates;
+
+@Certificates(baseDir = "target/certs", certificates = {
+        @Certificate(name = "test-formats-encrypted-pem", password = "password", formats = { Format.JKS, Format.ENCRYPTED_PEM,
+                Format.PKCS12 })
+})
+public class DefaultEncryptedPemKeyStoreTest {
+
+    private static final String configuration = """
+            quarkus.tls.key-store.pem.foo.cert=target/certs/test-formats-encrypted-pem.crt
+            quarkus.tls.key-store.pem.foo.key=target/certs/test-formats-encrypted-pem.key
+            quarkus.tls.key-store.pem.foo.password=password
+            """;
+
+    @RegisterExtension
+    static final QuarkusUnitTest config = new QuarkusUnitTest().setArchiveProducer(
+            () -> ShrinkWrap.create(JavaArchive.class)
+                    .add(new StringAsset(configuration), "application.properties"));
+
+    @Inject
+    TlsConfigurationRegistry certificates;
+
+    @Test
+    void test() throws KeyStoreException, CertificateParsingException {
+        TlsConfiguration def = certificates.getDefault().orElseThrow();
+
+        assertThat(def.getKeyStoreOptions()).isNotNull();
+        assertThat(def.getKeyStore()).isNotNull();
+
+        // dummy-entry-x is the alias of the certificate in the keystore generated by Vert.x.
+
+        X509Certificate certificate = (X509Certificate) def.getKeyStore().getCertificate("dummy-entry-0");
+        assertThat(certificate).isNotNull();
+        assertThat(certificate.getSubjectAlternativeNames()).anySatisfy(l -> {
+            assertThat(l.get(0)).isEqualTo(2);
+            assertThat(l.get(1)).isEqualTo("localhost");
+        });
+    }
+}

extensions/tls-registry/deployment/src/test/java/io/quarkus/tls/EncryptedPemWithNoPasswordTest.java

@@ -0,0 +1,41 @@
+package io.quarkus.tls;
+
+import static org.assertj.core.api.Assertions.assertThat;
+import static org.assertj.core.api.Assertions.fail;
+
+import java.security.KeyStoreException;
+import java.security.cert.CertificateParsingException;
+
+import org.jboss.shrinkwrap.api.ShrinkWrap;
+import org.jboss.shrinkwrap.api.asset.StringAsset;
+import org.jboss.shrinkwrap.api.spec.JavaArchive;
+import org.junit.jupiter.api.Test;
+import org.junit.jupiter.api.extension.RegisterExtension;
+
+import io.quarkus.test.QuarkusUnitTest;
+import io.smallrye.certs.Format;
+import io.smallrye.certs.junit5.Certificate;
+import io.smallrye.certs.junit5.Certificates;
+
+@Certificates(baseDir = "target/certs", certificates = {
+        @Certificate(name = "test-formats-encrypted-pem", password = "password", formats = { Format.JKS, Format.ENCRYPTED_PEM,
+                Format.PKCS12 })
+})
+public class EncryptedPemWithNoPasswordTest {
+
+    private static final String configuration = """
+            quarkus.tls.key-store.pem.foo.cert=target/certs/test-formats-encrypted-pem.crt
+            quarkus.tls.key-store.pem.foo.key=target/certs/test-formats-encrypted-pem.key
+            """;
+
+    @RegisterExtension
+    static final QuarkusUnitTest config = new QuarkusUnitTest().setArchiveProducer(
+            () -> ShrinkWrap.create(JavaArchive.class)
+                    .add(new StringAsset(configuration), "application.properties"))
+            .assertException(t -> assertThat(t.getMessage()).contains("key/certificate pair", "default"));
+
+    @Test
+    void test() throws KeyStoreException, CertificateParsingException {
+        fail("Should not be called as the extension should fail before.");
+    }
+}

extensions/tls-registry/deployment/src/test/java/io/quarkus/tls/EncryptedPemWithWrongPasswordTest.java

@@ -0,0 +1,42 @@
+package io.quarkus.tls;
+
+import static org.assertj.core.api.Assertions.assertThat;
+import static org.assertj.core.api.Assertions.fail;
+
+import java.security.KeyStoreException;
+import java.security.cert.CertificateParsingException;
+
+import org.jboss.shrinkwrap.api.ShrinkWrap;
+import org.jboss.shrinkwrap.api.asset.StringAsset;
+import org.jboss.shrinkwrap.api.spec.JavaArchive;
+import org.junit.jupiter.api.Test;
+import org.junit.jupiter.api.extension.RegisterExtension;
+
+import io.quarkus.test.QuarkusUnitTest;
+import io.smallrye.certs.Format;
+import io.smallrye.certs.junit5.Certificate;
+import io.smallrye.certs.junit5.Certificates;
+
+@Certificates(baseDir = "target/certs", certificates = {
+        @Certificate(name = "test-formats-encrypted-pem", password = "password", formats = { Format.JKS, Format.ENCRYPTED_PEM,
+                Format.PKCS12 })
+})
+public class EncryptedPemWithWrongPasswordTest {
+
+    private static final String configuration = """
+            quarkus.tls.key-store.pem.foo.cert=target/certs/test-formats-encrypted-pem.crt
+            quarkus.tls.key-store.pem.foo.key=target/certs/test-formats-encrypted-pem.key
+            quarkus.tls.key-store.pem.foo.password=wrong
+            """;
+
+    @RegisterExtension
+    static final QuarkusUnitTest config = new QuarkusUnitTest().setArchiveProducer(
+            () -> ShrinkWrap.create(JavaArchive.class)
+                    .add(new StringAsset(configuration), "application.properties"))
+            .assertException(t -> assertThat(t.getMessage()).contains("key/certificate pair", "default"));
+
+    @Test
+    void test() throws KeyStoreException, CertificateParsingException {
+        fail("Should not be called as the extension should fail before.");
+    }
+}

extensions/tls-registry/deployment/src/test/java/io/quarkus/tls/NamedEncryptedPemKeyStoreTest.java

@@ -0,0 +1,60 @@
+package io.quarkus.tls;
+
+import static org.assertj.core.api.Assertions.assertThat;
+
+import java.security.KeyStoreException;
+import java.security.cert.CertificateParsingException;
+import java.security.cert.X509Certificate;
+
+import jakarta.inject.Inject;
+
+import org.jboss.shrinkwrap.api.ShrinkWrap;
+import org.jboss.shrinkwrap.api.asset.StringAsset;
+import org.jboss.shrinkwrap.api.spec.JavaArchive;
+import org.junit.jupiter.api.Test;
+import org.junit.jupiter.api.extension.RegisterExtension;
+
+import io.quarkus.test.QuarkusUnitTest;
+import io.smallrye.certs.Format;
+import io.smallrye.certs.junit5.Certificate;
+import io.smallrye.certs.junit5.Certificates;
+
+@Certificates(baseDir = "target/certs", certificates = {
+        @Certificate(name = "test-formats-encrypted-pem", password = "password", formats = { Format.JKS, Format.ENCRYPTED_PEM,
+                Format.PKCS12 })
+})
+public class NamedEncryptedPemKeyStoreTest {
+
+    private static final String configuration = """
+            quarkus.tls.http.key-store.pem.foo.cert=target/certs/test-formats-encrypted-pem.crt
+            quarkus.tls.http.key-store.pem.foo.key=target/certs/test-formats-encrypted-pem.key
+            quarkus.tls.http.key-store.pem.foo.password=password
+            """;
+
+    @RegisterExtension
+    static final QuarkusUnitTest config = new QuarkusUnitTest().setArchiveProducer(
+            () -> ShrinkWrap.create(JavaArchive.class)
+                    .add(new StringAsset(configuration), "application.properties"));
+
+    @Inject
+    TlsConfigurationRegistry certificates;
+
+    @Test
+    void test() throws KeyStoreException, CertificateParsingException {
+        TlsConfiguration def = certificates.getDefault().orElseThrow();
+        TlsConfiguration named = certificates.get("http").orElseThrow();
+
+        assertThat(def.getKeyStoreOptions()).isNull();
+        assertThat(def.getKeyStore()).isNull();
+
+        assertThat(named.getKeyStoreOptions()).isNotNull();
+        assertThat(named.getKeyStore()).isNotNull();
+
+        X509Certificate certificate = (X509Certificate) named.getKeyStore().getCertificate("dummy-entry-0");
+        assertThat(certificate).isNotNull();
+        assertThat(certificate.getSubjectAlternativeNames()).anySatisfy(l -> {
+            assertThat(l.get(0)).isEqualTo(2);
+            assertThat(l.get(1)).isEqualTo("localhost");
+        });
+    }
+}

extensions/tls-registry/runtime/pom.xml

@@ -26,6 +26,10 @@
             <groupId>io.quarkus</groupId>
             <artifactId>quarkus-credentials</artifactId>
         </dependency>
+        <dependency>
+            <groupId>io.smallrye.certs</groupId>
+            <artifactId>smallrye-private-key-pem-parser</artifactId>
+        </dependency>
 
         <!-- To register the let's encrypt routes -->
         <dependency>

extensions/tls-registry/runtime/src/main/java/io/quarkus/tls/runtime/config/PemKeyCertConfig.java

@@ -2,6 +2,7 @@
 
 import static io.quarkus.tls.runtime.config.TlsConfigUtils.read;
 
+import java.nio.charset.StandardCharsets;
 import java.nio.file.Path;
 import java.util.ArrayList;
 import java.util.List;
@@ -10,6 +11,7 @@
 import java.util.TreeMap;
 
 import io.quarkus.runtime.annotations.ConfigGroup;
+import io.smallrye.certs.pem.parsers.EncryptedPKCS8Parser;
 import io.smallrye.config.WithParentName;
 import io.vertx.core.buffer.Buffer;
 import io.vertx.core.net.PemKeyCertOptions;
@@ -62,22 +64,37 @@ default PemKeyCertOptions toOptions() {
 
         for (KeyCertConfig config : orderedListOfPair) {
             options.addCertValue(Buffer.buffer(read(config.cert())));
-            options.addKeyValue(Buffer.buffer(read(config.key())));
+            if (config.password().isPresent()) {
+                byte[] content = read(config.key());
+                String contentAsString = new String(content, StandardCharsets.UTF_8);
+                Buffer decrypted = new EncryptedPKCS8Parser().decryptKey(contentAsString, config.password().get());
+                if (decrypted == null) {
+                    throw new IllegalArgumentException("Unable to decrypt the key file: " + config.key());
+                }
+                options.addKeyValue(decrypted);
+            } else {
+                options.addKeyValue(Buffer.buffer(read(config.key())));
+            }
         }
         return options;
     }
 
     interface KeyCertConfig {
 
         /**
-         * The path to the key file (in PEM format).
+         * The path to the key file (in PEM format: PKCS#8, PKCS#1 or encrypted PKCS#8).
          */
         Path key();
 
         /**
          * The path to the certificate file (in PEM format).
          */
         Path cert();
+
+        /**
+         * When the key is encrypted (encrypted PKCS#8), the password to decrypt it.
+         */
+        Optional<String> password();
     }
 
 }

pom.xml

@@ -87,7 +87,7 @@
         <proto-google-common-protos.version>2.46.0</proto-google-common-protos.version>
 
         <!-- Used in the build parent and test BOM (for the junit 5 plugin) and in the BOM (for the API) -->
-        <smallrye-certificate-generator.version>0.8.1</smallrye-certificate-generator.version>
+        <smallrye-certificate-generator.version>0.9.2</smallrye-certificate-generator.version>
 
         <!-- TestNG version: we don't enforce it in the BOM as it is mostly used in the MP TCKs and we need to use the version from the TCKs -->
         <testng.version>7.8.0</testng.version>