/*
    * Copyright 2024 The Netty Project
    *
    * The Netty Project licenses this file to you 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 io.netty.pkitesting;
  
  import io.netty.util.internal.EmptyArrays;
  import org.bouncycastle.asn1.ASN1Integer;
  import org.bouncycastle.asn1.ASN1ObjectIdentifier;
  import org.bouncycastle.asn1.DERBitString;
  import org.bouncycastle.asn1.DERIA5String;
  import org.bouncycastle.asn1.DERUTF8String;
  import org.bouncycastle.asn1.x500.X500Name;
  import org.bouncycastle.asn1.x509.AlgorithmIdentifier;
  import org.bouncycastle.asn1.x509.BasicConstraints;
  import org.bouncycastle.asn1.x509.CRLDistPoint;
  import org.bouncycastle.asn1.x509.DistributionPoint;
  import org.bouncycastle.asn1.x509.DistributionPointName;
  import org.bouncycastle.asn1.x509.Extension;
  import org.bouncycastle.asn1.x509.ExtensionsGenerator;
  import org.bouncycastle.asn1.x509.GeneralName;
  import org.bouncycastle.asn1.x509.GeneralNames;
  import org.bouncycastle.asn1.x509.KeyPurposeId;
  import org.bouncycastle.asn1.x509.SubjectPublicKeyInfo;
  import org.bouncycastle.asn1.x509.Time;
  import org.bouncycastle.asn1.x509.V3TBSCertificateGenerator;
  import org.bouncycastle.jcajce.spec.EdDSAParameterSpec;
  
  import java.io.IOException;
  import java.io.UncheckedIOException;
  import java.math.BigInteger;
  import java.net.InetAddress;
  import java.net.URI;
  import java.net.URISyntaxException;
  import java.security.GeneralSecurityException;
  import java.security.KeyPair;
  import java.security.KeyPairGenerator;
  import java.security.PrivateKey;
  import java.security.PublicKey;
  import java.security.SecureRandom;
  import java.security.cert.CertificateFactory;
  import java.security.cert.X509Certificate;
  import java.security.interfaces.DSAPublicKey;
  import java.security.interfaces.ECPublicKey;
  import java.security.interfaces.RSAPublicKey;
  import java.security.spec.AlgorithmParameterSpec;
  import java.security.spec.ECGenParameterSpec;
  import java.security.spec.RSAKeyGenParameterSpec;
  import java.time.Instant;
  import java.time.temporal.ChronoUnit;
  import java.util.ArrayList;
  import java.util.Date;
  import java.util.List;
  import java.util.OptionalInt;
  import java.util.Set;
  import java.util.TreeSet;
  import javax.security.auth.x500.X500Principal;
  
  import static java.util.Objects.requireNonNull;
  
  /**
   * The {@link CertificateBuilder} produce {@link X509Bundle} instances, where the keys use the specified
   * algorithm, and the certificate have the specified data.
   * <p>
   * The builder can make self-signed bundles, or can make bundles that are signed by other bundles to build a verified
   * certificate path.
   * <p>
   * The builder can also make certificate that are invalid in various ways, for testing purpose.
   * The most typical application is to make a certificate that has already expired or is not yet valid.
   * <p>
   * See RFC 5280 for the details of X.509 certificate contents.
   * <p>
   * Here is an example where a leaf certificate is created and signed by a self-signed issuer certificate:
   * <pre>{@code
   * Instant now = Instant.now();
   * CertificateBuilder template = new CertificateBuilder()
   *             .notBefore(now.minus(1, DAYS))
   *             .notAfter(now.plus(1, DAYS));
   * X509Bundle issuer = template.copy()
   *             .subject("CN=testca, OU=dept, O=your-org")
   *             .setKeyUsage(true, KeyUsage.digitalSignature, KeyUsage.keyCertSign)
   *             .setIsCertificateAuthority(true)
   *             .buildSelfSigned();
   * X509Bundle leaf = template.copy()
   *             .subject("CN=leaf, OU=dept, O=your-org")
   *             .setKeyUsage(true, KeyUsage.digitalSignature)
   *             .addExtendedKeyUsage(ExtendedKeyUsage.PKIX_KP_SERVER_AUTH)
   *             .addSanDnsName("san-1.leaf.dept.your-org.com")
  *             .buildIssuedBy(issuer);
  * }</pre>
  */
 public final class CertificateBuilder {
 
     static final String OID_X509_NAME_CONSTRAINTS = "2.5.29.30";
     static final String OID_PKIX_KP = "1.3.6.1.5.5.7.3";
     static final String OID_PKIX_KP_SERVER_AUTH = OID_PKIX_KP + ".1";
     static final String OID_PKIX_KP_CLIENT_AUTH = OID_PKIX_KP + ".2";
     static final String OID_PKIX_KP_CODE_SIGNING = OID_PKIX_KP + ".3";
     static final String OID_PKIX_KP_EMAIL_PROTECTION = OID_PKIX_KP + ".4";
     static final String OID_PKIX_KP_TIME_STAMPING = OID_PKIX_KP + ".8";
     static final String OID_PKIX_KP_OCSP_SIGNING = OID_PKIX_KP + ".9";
     static final String OID_KERBEROS_KEY_PURPOSE_CLIENT_AUTH = "1.3.6.1.5.2.3.4";
     static final String OID_MICROSOFT_SMARTCARD_LOGIN = "1.3.6.1.4.1.311.20.2.2";
     private static final GeneralName[] EMPTY_GENERAL_NAMES = new GeneralName[0];
     private static final DistributionPoint[] EMPTY_DIST_POINTS = new DistributionPoint[0];
     private static final AlgorithmParameterSpec UNSUPPORTED_SPEC = new AlgorithmParameterSpec() {
     };
 
     SecureRandom random;
     Algorithm algorithm = Algorithm.ecp256;
     Instant notBefore = Instant.now().minus(1, ChronoUnit.DAYS);
     Instant notAfter = Instant.now().plus(1, ChronoUnit.DAYS);
     List<BuilderCallback> modifierCallbacks = new ArrayList<>();
     List<GeneralName> subjectAlternativeNames = new ArrayList<>();
     List<DistributionPoint> crlDistributionPoints = new ArrayList<>();
     BigInteger serial;
     X500Principal subject;
     boolean isCertificateAuthority;
     OptionalInt pathLengthConstraint = OptionalInt.empty();
     PublicKey publicKey;
     Set<String> extendedKeyUsage = new TreeSet<>();
     Extension keyUsage;
 
     /**
      * Create a new certificate builder with a default configuration.
      * Unless specified otherwise, the builder will produce bundles that use the
      * {@linkplain Algorithm#ecp256 NIST EC-P 256} key algorithm,
      * and the certificates will be valid as of yesterday and expire tomorrow.
      */
     public CertificateBuilder() {
     }
 
     /**
      * Produce a copy of the current state in this certificate builder.
      * @return A copy of this certificate builder.
      */
     public CertificateBuilder copy() {
         CertificateBuilder copy = new CertificateBuilder();
         copy.random = random;
         copy.algorithm = algorithm;
         copy.notBefore = notBefore;
         copy.notAfter = notAfter;
         copy.modifierCallbacks = new ArrayList<>(modifierCallbacks);
         copy.subjectAlternativeNames = new ArrayList<>(subjectAlternativeNames);
         copy.crlDistributionPoints = new ArrayList<>(crlDistributionPoints);
         copy.serial = serial;
         copy.subject = subject;
         copy.isCertificateAuthority = isCertificateAuthority;
         copy.pathLengthConstraint = pathLengthConstraint;
         copy.publicKey = publicKey;
         copy.keyUsage = keyUsage;
         copy.extendedKeyUsage = new TreeSet<>(extendedKeyUsage);
         return copy;
     }
 
     /**
      * Set the {@link SecureRandom} instance to use when generating keys.
      * @param secureRandom The secure random instance to use.
      * @return This certificate builder.
      */
     public CertificateBuilder secureRandom(SecureRandom secureRandom) {
         random = requireNonNull(secureRandom);
         return this;
     }
 
     /**
      * Set the not-before field of the certificate. The certificate will not be valid before this time.
      * @param instant The not-before time.
      * @return This certificate builder.
      */
     public CertificateBuilder notBefore(Instant instant) {
         notBefore = requireNonNull(instant);
         return this;
     }
 
     /**
      * Set the not-after field of the certificate. The certificate will not be valid after this time.
      * @param instant The not-after time.
      * @return This certificate builder.
      */
     public CertificateBuilder notAfter(Instant instant) {
         notAfter = requireNonNull(instant);
         return this;
     }
 
     /**
      * Set the specific serial number to use in the certificate.
      * One will be generated randomly, if none is specified.
      * @param serial The serial number to use, or {@code null}.
      * @return This certificate builder.
      */
     public CertificateBuilder serial(BigInteger serial) {
         this.serial = serial;
         return this;
     }
 
     /**
      * Set the fully-qualified domain name (an X.500 name) as the subject of the certificate.
      * @param fqdn The subject name to use.
      * @return This certificate builder.
      */
     public CertificateBuilder subject(String fqdn) {
         subject = new X500Principal(requireNonNull(fqdn));
         return this;
     }
 
     /**
      * Set the subject name of the certificate to the given {@link X500Principal}.
      * @param name The subject name to use.
      * @return This certificate builder.
      */
     public CertificateBuilder subject(X500Principal name) {
         subject = requireNonNull(name);
         return this;
     }
 
     /**
      * Add an Other Name to the Subject Alternative Names, of the given OID type, and with the given encoded value.
      * The type and value will be wrapped in a SEQUENCE.
      * @param typeOid The OID type of the Other Name value.
      * @param encodedValue The encoded Other Name value.
      * @return This certificate builder.
      */
     public CertificateBuilder addSanOtherName(String typeOid, byte[] encodedValue) {
         subjectAlternativeNames.add(GeneralNameUtils.otherName(typeOid, encodedValue));
         return this;
     }
 
     /**
      * Add an RFC 822 name to the Subject Alternative Names.
      * The RFC 822 standard is the obsolete specification for email, so these SANs are email addresses.
      * @param name The email address to add to the SANs.
      * @return This certificate builder.
      */
     public CertificateBuilder addSanRfc822Name(String name) {
         subjectAlternativeNames.add(GeneralNameUtils.rfc822Name(name));
         return this;
     }
 
     /**
      * Add a DNS name to the Subject Alternate Names.
      * @param dns The DNS name to add.
      * @return This certificate builder.
      */
     public CertificateBuilder addSanDnsName(String dns) {
         if (dns.trim().isEmpty()) {
             throw new IllegalArgumentException("Blank DNS SANs are forbidden by RFC 5280, Section 4.2.1.6.");
         }
         subjectAlternativeNames.add(GeneralNameUtils.dnsName(dns));
         return this;
     }
 
     // x400Address support intentionally omitted; not in common use.
 
     /**
      * Add a Directory Name to the Subject Alternative Names.
      * These are LDAP directory paths.
      * @param dirName The directory name to add to the SANs.
      * @return This certificate builder.
      */
     public CertificateBuilder addSanDirectoryName(String dirName) {
         subjectAlternativeNames.add(GeneralNameUtils.directoryName(dirName));
         return this;
     }
 
     // ediPartyName support intentionally omitted; not in common use.
 
     /**
      * Add a URI name to the Subject Alternative Names.
      * @param uri The URI to add to the SANs.
      * @return This certificate builder.
      */
     public CertificateBuilder addSanUriName(String uri) throws URISyntaxException {
         subjectAlternativeNames.add(GeneralNameUtils.uriName(uri));
         return this;
     }
 
     /**
      * Add a URI name to the Subject Alternative Names.
      * @param uri The URI to add to the SANs.
      * @return This certificate builder.
      */
     public CertificateBuilder addSanUriName(URI uri) {
         subjectAlternativeNames.add(GeneralNameUtils.uriName(uri));
         return this;
     }
 
     /**
      * Add an IP address to the Subject Alternative Names.
      * IPv4 and IPv6 addresses are both supported and converted to their correct encoding.
      * @param ipAddress The IP address to add to the SANs.
      * @return This certificate builder.
      */
     public CertificateBuilder addSanIpAddress(String ipAddress) {
         subjectAlternativeNames.add(GeneralNameUtils.ipAddress(ipAddress));
         return this;
     }
 
     /**
      * Add an IP address to the Subject Alternative Names.
      * IPv4 and IPv6 addresses are both supported and converted to their correct encoding.
      * @param ipAddress The IP address to add to the SANs.
      * @return This certificate builder.
      */
     public CertificateBuilder addSanIpAddress(InetAddress ipAddress) {
         subjectAlternativeNames.add(GeneralNameUtils.ipAddress(ipAddress.getHostAddress()));
         return this;
     }
 
     /**
      * Add a registeredID to the Subject Alternative Names.
      * A registeredID is an OBJECT IDENTIFIER, or OID, in ASN.1 speak.
      * @param oid The OID to add to the SANs.
      * @return This certificate builder.
      */
     public CertificateBuilder addSanRegisteredId(String oid) {
         subjectAlternativeNames.add(GeneralNameUtils.registeredId(oid));
         return this;
     }
 
     /**
      * Add a URI distribution point for a certificate revocation list.
      * <p>
      * If you are testing certificate revocation using the {@link RevocationServer},
      * you would obtain this URI from {@link RevocationServer#getCrlUri(X509Bundle)} with your intended issuer
      * certificate bundle.
      *
      * @param uri The URI for the CRL file.
      * @return This certificate builder.
      */
     public CertificateBuilder addCrlDistributionPoint(URI uri) {
         GeneralName fullName = GeneralNameUtils.uriName(uri);
         crlDistributionPoints.add(new DistributionPoint(
                 new DistributionPointName(new GeneralNames(fullName)),
                 null,
                 null));
         return this;
     }
 
     /**
      * Add a URI distribution point for a certificate revocation list.
      * <p>
      * If you are testing certificate revocation using the {@link RevocationServer},
      * you would obtain this URI from {@link RevocationServer#getCrlUri(X509Bundle)} with your intended issuer
      * certificate bundle.
      *
      * @param uri The URI for the CRL file.
      * @param issuer The issuer that signs the CRL file.
      * This MUST be {@code null} if the CRL issuer is also the issuer of the certificate being built.
      * Otherwise, if this certificate and the CRL will be signed by different issuers, then this MUST be the subject
      * name of the CRL signing certificate.
      * @return This certificate builder.
      */
     public CertificateBuilder addCrlDistributionPoint(URI uri, X500Principal issuer) {
         GeneralName fullName = GeneralNameUtils.uriName(uri);
         GeneralName issuerName = GeneralNameUtils.directoryName(issuer);
         crlDistributionPoints.add(new DistributionPoint(
                 new DistributionPointName(new GeneralNames(fullName)),
                 null,
                 new GeneralNames(issuerName)));
         return this;
     }
 
     /**
      * Set the certificate authority field.
      * If this is set to {@code true}, then this builder can build self-signed certificates, and those certifiactes
      * can be used to sign other certificates.
      * @param isCA {@code true} if this builder should make CA certificates.
      * @return This certificate builder.
      */
     public CertificateBuilder setIsCertificateAuthority(boolean isCA) {
         isCertificateAuthority = isCA;
         return this;
     }
 
     /**
      * Certificate Authority certificates may impose a limit to the length of the verified certificate path they permit.
      * @param pathLengthConstraint The maximum verified path length, if any.
      * @return This certificate builder.
      */
     public CertificateBuilder setPathLengthConstraint(OptionalInt pathLengthConstraint) {
         this.pathLengthConstraint = requireNonNull(pathLengthConstraint, "pathLengthConstraint");
         return this;
     }
 
     /**
      * Set the key algorithm to use. This also determines how certificates are signed.
      * @param algorithm The algorithm to use when generating the private key.
      * @return This certificate builder.
      */
     public CertificateBuilder algorithm(Algorithm algorithm) {
         requireNonNull(algorithm, "algorithm");
         if (algorithm.parameterSpec == UNSUPPORTED_SPEC) {
             throw new UnsupportedOperationException("This algorithm is not supported: " + algorithm);
         }
         this.algorithm = algorithm;
         return this;
     }
 
     /**
      * Make this certificate builder use the {@linkplain Algorithm#ecp256 NIST EC-P 256} elliptic curve key algorithm.
      * This algorithm provides a good balance between security, compatibility, performance, and key & signature sizes.
      * @return This certificate builder.
      * @see Algorithm#ecp256
      */
     public CertificateBuilder ecp256() {
         return algorithm(Algorithm.ecp256);
     }
 
     /**
      * Make this certificate builder use the {@linkplain Algorithm#rsa2048 2048-bit RSA} encryption and signing
      * algorithm. This algorithm provides maximum compatibility, but keys are large and slow to generate.
      * @return This certificate builder.
      * @see Algorithm#rsa2048
      */
     public CertificateBuilder rsa2048() {
         return algorithm(Algorithm.rsa2048);
     }
 
     /**
      * Instruct the certificate builder to not generate its own key pair, but to instead create a certificate that
      * uses the given public key.
      * <p>
      * This method is useful if you want to use an existing key-pair, e.g. to emulate a certificate authority
      * responding to a Certificate Signing Request (CSR).
      * <p>
      * If the given public key is {@code null} (the default) then a new key-pair will be generated instead.
      *
      * @param key The public key to wrap in a certificate.
      * @return This certificate builder.
      */
     public CertificateBuilder publicKey(PublicKey key) {
         publicKey = key;
         return this;
     }
 
     private CertificateBuilder addExtension(String identifierOid, boolean critical, byte[] value) {
         requireNonNull(identifierOid, "identifierOid");
         requireNonNull(value, "value");
         modifierCallbacks.add(builder -> {
             builder.addExtension(new Extension(
                     new ASN1ObjectIdentifier(identifierOid),
                     critical,
                     value));
         });
         return this;
     }
 
     /**
      * Add a custom extension to the certificate, with the given OID, criticality flag, and DER-encoded contents.
      * @param identifierOID The OID identifying the extension.
      * @param critical {@code true} if the extension is critical, otherwise {@code false}.
      * Certificate systems MUST reject certificates with critical extensions they don't recognize.
      * @param contents The DER-encoded extension contents.
      * @return This certificate builder.
      */
     public CertificateBuilder addExtensionOctetString(String identifierOID, boolean critical, byte[] contents) {
         requireNonNull(identifierOID, "identifierOID");
         requireNonNull(contents, "contents");
         modifierCallbacks.add(builder -> {
             builder.addExtension(new Extension(
                     new ASN1ObjectIdentifier(identifierOID),
                     critical,
                     contents));
         });
         return this;
     }
 
     /**
      * Add a custom DER-encoded ASN.1 UTF-8 string extension to the certificate, with the given OID, criticality,
      * and string value.
      * The string will be converted to its proper binary encoding by this method.
      * @param identifierOID The OID identifying the extension.
      * @param critical {@code true} if the extension is critical, otherwise {@code false}.
      * Certificate systems MUST reject certificates with critical extensions they don't recognize.
      * @param value The string value.
      * @return This certificate builder.
      */
     public CertificateBuilder addExtensionUtf8String(String identifierOID, boolean critical, String value) {
         try {
             return addExtension(identifierOID, critical, new DERUTF8String(value).getEncoded("DER"));
         } catch (IOException e) {
             throw new UncheckedIOException(e);
         }
     }
 
     /**
      * Add a custom DER-encoded ASN.1 IA5String (an ASCII string) extension to the certificate, with the given OID,
      * criticality, and string value.
      * The string will be converted to its proper binary encoding by this method.
      * @param identifierOID The OID identifying the extension.
      * @param critical {@code true} if the extension is critical, otherwise {@code false}.
      * Certificate systems MUST reject certificates with critical extensions they don't recognize.
      * @param value The string value.
      * @return This certificate builder.
      */
     public CertificateBuilder addExtensionAsciiString(String identifierOID, boolean critical, String value) {
         try {
             return addExtension(identifierOID, critical, new DERIA5String(value).getEncoded("DER"));
         } catch (IOException e) {
             throw new UncheckedIOException(e);
         }
     }
 
     /**
      * The key usage specify the intended usages for which the certificate has been issued.
      * Some are overlapping, some are deprecated, and some are implied by usage.
      * <p>
      * For Certificate Authority usage, the important ones are {@link KeyUsage#keyCertSign}
      * and {@link KeyUsage#cRLSign}.
      * <p>
      * Any certificate that has {@link KeyUsage#keyCertSign} must also have {@link #setIsCertificateAuthority(boolean)}
      * set to {@code true}.
      *
      * @param critical {@code true} if certificate recipients are required to understand all the set bits,
      * otherwise {@code false}.
      * @param keyUsages The key usages to set.
      * @return This certificate builder.
      */
     public CertificateBuilder setKeyUsage(boolean critical, KeyUsage... keyUsages) {
         int maxBit = 0;
         for (KeyUsage usage : keyUsages) {
             maxBit = Math.max(usage.bitId, maxBit);
         }
         boolean[] bits = new boolean[maxBit + 1];
         for (KeyUsage usage : keyUsages) {
             bits[usage.bitId] = true;
         }
         int padding = 8 - bits.length % 8;
         int lenBytes = bits.length / 8 + 1;
         if (padding == 8) {
             padding = 0;
             lenBytes--;
         }
         byte[] bytes = new byte[lenBytes];
         for (int i = 0; i < bits.length; i++) {
             if (bits[i]) {
                 int byteIndex = i / 8;
                 int bitIndex = i % 8;
                 bytes[byteIndex] |= (byte) (0x80 >>> bitIndex);
             }
         }
 
         try {
             keyUsage = new Extension(
                     Extension.keyUsage,
                     critical,
                     new DERBitString(bytes, padding).getEncoded("DER"));
         } catch (IOException e) {
             throw new UncheckedIOException(e);
         }
         return this;
     }
 
     /**
      * Add the given OID to the list of extended key usages.
      * @param oid The OID to add.
      * @return This certificate builder.
      * @see ExtendedKeyUsage
      * @see #addExtendedKeyUsage(ExtendedKeyUsage)
      */
     public CertificateBuilder addExtendedKeyUsage(String oid) {
         extendedKeyUsage.add(oid);
         return this;
     }
 
     /**
      * Add the given {@link ExtendedKeyUsage} to the list of extended key usages.
      * @param keyUsage The extended key usage to add.
      * @return This certificate builder.
      */
     public CertificateBuilder addExtendedKeyUsage(ExtendedKeyUsage keyUsage) {
         extendedKeyUsage.add(keyUsage.getOid());
         return this;
     }
 
     /**
      * Add server-authentication to the list of extended key usages.
      * @return This certificate builder.
      */
     public CertificateBuilder addExtendedKeyUsageServerAuth() {
         return addExtendedKeyUsage(ExtendedKeyUsage.PKIX_KP_SERVER_AUTH);
     }
 
     /**
      * Add client-authentication to the list of extended key usages.
      * @return This certificate builder.
      */
     public CertificateBuilder addExtendedKeyUsageClientAuth() {
         return addExtendedKeyUsage(ExtendedKeyUsage.PKIX_KP_CLIENT_AUTH);
     }
 
     /**
      * Add code signing to the list of extended key usages.
      * @return This certificate builder.
      */
     public CertificateBuilder addExtendedKeyUsageCodeSigning() {
         return addExtendedKeyUsage(ExtendedKeyUsage.PKIX_KP_CODE_SIGNING);
     }
 
     /**
      * Add email protection to the list of extended key usages.
      * @return This certificate builder.
      */
     public CertificateBuilder addExtendedKeyUsageEmailProtection() {
         return addExtendedKeyUsage(ExtendedKeyUsage.PKIX_KP_EMAIL_PROTECTION);
     }
 
     /**
      * Add time-stamping to the list of extended key usages.
      * @return This certificate builder.
      */
     public CertificateBuilder addExtendedKeyUsageTimeStamping() {
         return addExtendedKeyUsage(ExtendedKeyUsage.PKIX_KP_TIME_STAMPING);
     }
 
     /**
      * Add OCSP signing to the list of extended key usages.
      * @return This certificate builder.
      */
     public CertificateBuilder addExtendedKeyUsageOcspSigning() {
         return addExtendedKeyUsage(ExtendedKeyUsage.PKIX_KP_OCSP_SIGNING);
     }
 
     /**
      * Add Kerberos client authentication to the list of extended key usages.
      * @return This certificate builder.
      */
     public CertificateBuilder addExtendedKeyUsageKerberosClientAuth() {
         return addExtendedKeyUsage(ExtendedKeyUsage.KERBEROS_KEY_PURPOSE_CLIENT_AUTH);
     }
 
     /**
      * Add Microsoft smartcard login to the list of extended key usages.
      * @return This certificate builder.
      */
     public CertificateBuilder addExtendedKeyUsageMicrosoftSmartcardLogin() {
         return addExtendedKeyUsage(ExtendedKeyUsage.MICROSOFT_SMARTCARD_LOGIN);
     }
 
     /**
      * Build a {@link X509Bundle} with a self-signed certificate.
      * @return The newly created bundle.
      * @throws Exception If something went wrong in the process.
      */
     public X509Bundle buildSelfSigned() throws Exception {
         if (publicKey != null) {
             throw new IllegalStateException("Cannot create a self-signed certificate with a public key from a CSR.");
         }
         KeyPair keyPair = generateKeyPair();
 
         V3TBSCertificateGenerator generator = createCertBuilder(subject, subject, keyPair, algorithm.signatureType);
 
         addExtensions(generator);
 
         Signed signed = new Signed(tbsCertToBytes(generator), algorithm.signatureType, keyPair.getPrivate());
         CertificateFactory factory = CertificateFactory.getInstance("X.509");
         X509Certificate cert = (X509Certificate) factory.generateCertificate(signed.toInputStream());
         return X509Bundle.fromRootCertificateAuthority(cert, keyPair);
     }
 
     /**
      * Build a {@link X509Bundle} with a certificate signed by the given issuer bundle.
      * The signing algorithm used will be derived from the issuers public key.
      * @return The newly created bundle.
      * @throws Exception If something went wrong in the process.
      */
     public X509Bundle buildIssuedBy(X509Bundle issuerBundle) throws Exception {
         String issuerSignAlgorithm = preferredSignatureAlgorithm(issuerBundle.getCertificate().getPublicKey());
         return buildIssuedBy(issuerBundle, issuerSignAlgorithm);
     }
 
     /**
      * Build a {@link X509Bundle} with a certificate signed by the given issuer bundle, using the specified
      * signing algorithm.
      * @return The newly created bundle.
      * @throws Exception If something went wrong in the process.
      */
     public X509Bundle buildIssuedBy(X509Bundle issuerBundle, String signAlg) throws Exception {
         final KeyPair keyPair;
         if (publicKey == null) {
             keyPair = generateKeyPair();
         } else {
             keyPair = new KeyPair(publicKey, null);
         }
 
         X500Principal issuerPrincipal = issuerBundle.getCertificate().getSubjectX500Principal();
         V3TBSCertificateGenerator generator = createCertBuilder(issuerPrincipal, subject, keyPair, signAlg);
 
         addExtensions(generator);
 
         PrivateKey issuerPrivateKey = issuerBundle.getKeyPair().getPrivate();
         if (issuerPrivateKey == null) {
             throw new IllegalArgumentException(
                     "Cannot sign certificate with issuer bundle that does not have a private key.");
         }
         Signed signed = new Signed(tbsCertToBytes(generator), signAlg, issuerPrivateKey);
         CertificateFactory factory = CertificateFactory.getInstance("X.509");
         X509Certificate cert = (X509Certificate) factory.generateCertificate(signed.toInputStream());
         X509Certificate[] issuerPath = issuerBundle.getCertificatePath();
         X509Certificate[] path = new X509Certificate[issuerPath.length + 1];
         path[0] = cert;
         System.arraycopy(issuerPath, 0, path, 1, issuerPath.length);
         return X509Bundle.fromCertificatePath(path, issuerBundle.getRootCertificate(), keyPair);
     }
 
     private static String preferredSignatureAlgorithm(PublicKey key) {
         if (key instanceof RSAPublicKey) {
             RSAPublicKey rsa = (RSAPublicKey) key;
             if (rsa.getModulus().bitLength() < 4096) {
                 return "SHA256withRSA";
             }
             return "SHA384withRSA";
         }
         if (key instanceof ECPublicKey) {
             ECPublicKey ec = (ECPublicKey) key;
             int size = ec.getW().getAffineX().bitLength();
             // Note: the coords are not guaranteed to use up all available bits, hence less-than-or-equal checks.
             if (size <= 256) {
                 return "SHA256withECDSA";
             }
             if (size <= 384) {
                 return "SHA384withECDSA";
             }
             return "SHA512withECDSA";
         }
         if (key instanceof DSAPublicKey) {
             throw new IllegalArgumentException("DSA keys are not supported because they are obsolete.");
         }
         String keyAlgorithm = key.getAlgorithm();
         if ("Ed25519".equals(keyAlgorithm) || "1.3.101.112".equals(keyAlgorithm)) {
             return "Ed25519";
         }
         if ("Ed448".equals(keyAlgorithm) || "1.3.101.113".equals(keyAlgorithm)) {
             return "Ed448";
         }
         if ("EdDSA".equals(keyAlgorithm)) {
             byte[] encoded = key.getEncoded();
             if (encoded.length <= 44) {
                 return "Ed25519";
             }
             if (encoded.length <= 69) {
                 return "Ed448";
             }
         }
         throw new IllegalArgumentException("Don't know what signature algorithm is best for " + key);
     }
 
     private KeyPair generateKeyPair() throws GeneralSecurityException {
         return algorithm.generateKeyPair(getSecureRandom());
     }
 
     private V3TBSCertificateGenerator createCertBuilder(
             X500Principal issuer, X500Principal subject, KeyPair keyPair, String signAlg) {
         BigInteger serial = this.serial != null ? this.serial : new BigInteger(159, getSecureRandom());
         PublicKey pubKey = keyPair.getPublic();
 
         V3TBSCertificateGenerator generator = new V3TBSCertificateGenerator();
         generator.setIssuer(X500Name.getInstance(issuer.getEncoded()));
         if (subject != null) {
             generator.setSubject(X500Name.getInstance(subject.getEncoded()));
         }
         generator.setSerialNumber(new ASN1Integer(serial));
         generator.setSignature(new AlgorithmIdentifier(new ASN1ObjectIdentifier(
                 Algorithms.oidForAlgorithmName(signAlg))));
         generator.setStartDate(new Time(Date.from(notBefore)));
         generator.setEndDate(new Time(Date.from(notAfter)));
         generator.setSubjectPublicKeyInfo(SubjectPublicKeyInfo.getInstance(pubKey.getEncoded()));
         return generator;
     }
 
     private static byte[] tbsCertToBytes(V3TBSCertificateGenerator generator) {
         try {
             return generator.generateTBSCertificate().getEncoded("DER");
         } catch (IOException e) {
             throw new UncheckedIOException(e);
         }
     }
 
     private SecureRandom getSecureRandom() {
         SecureRandom rng = random;
         if (rng == null) {
             rng = SecureRandomHolder.RANDOM;
         }
         return rng;
     }
 
     private void addExtensions(V3TBSCertificateGenerator tbsCert) throws Exception {
         ExtensionsGenerator generator = new ExtensionsGenerator();
         if (isCertificateAuthority) {
             final BasicConstraints basicConstraints;
             if (pathLengthConstraint.isPresent()) {
                 basicConstraints = new BasicConstraints(pathLengthConstraint.getAsInt());
             } else {
                 basicConstraints = new BasicConstraints(true);
             }
             final byte[] basicConstraintsBytes = basicConstraints.getEncoded("DER");
             generator.addExtension(new Extension(Extension.basicConstraints, true, basicConstraintsBytes));
         }
         if (keyUsage != null) {
             generator.addExtension(keyUsage);
         }
 
         if (!extendedKeyUsage.isEmpty()) {
             KeyPurposeId[] usages = new KeyPurposeId[extendedKeyUsage.size()];
             String[] usagesStrings = extendedKeyUsage.toArray(EmptyArrays.EMPTY_STRINGS);
             for (int i = 0; i < usagesStrings.length; i++) {
                 usages[i] = KeyPurposeId.getInstance(new ASN1ObjectIdentifier(usagesStrings[i]));
             }
             byte[] der = new org.bouncycastle.asn1.x509.ExtendedKeyUsage(usages).getEncoded("DER");
             generator.addExtension(new Extension(Extension.extendedKeyUsage, false, der));
         }
 
         if (!subjectAlternativeNames.isEmpty()) {
             // SAN is critical extension if subject is empty sequence:
             boolean critical = subject.getName().isEmpty();
             byte[] result;
             GeneralNames generalNames = new GeneralNames(subjectAlternativeNames.toArray(EMPTY_GENERAL_NAMES));
             try {
                 result = generalNames.getEncoded("DER");
             } catch (IOException e) {
                 throw new UncheckedIOException(e);
             }
             generator.addExtension(new Extension(Extension.subjectAlternativeName, critical, result));
         }
 
         if (!crlDistributionPoints.isEmpty()) {
             generator.addExtension(Extension.create(
                     Extension.cRLDistributionPoints,
                     false,
                     new CRLDistPoint(crlDistributionPoints.toArray(EMPTY_DIST_POINTS))));
         }
 
         for (BuilderCallback callback : modifierCallbacks) {
             callback.modify(generator);
         }
 
         if (!generator.isEmpty()) {
             tbsCert.setExtensions(generator.generate());
         }
     }
 
     /**
      * The {@link Algorithm} enum encapsulates both the key type, key generation parameters, and the signature
      * algorithm to use.
      */
     public enum Algorithm {
         /**
          * The NIST P-256 elliptic curve algorithm, offer fast key generation, signing, and verification,
          * with small keys and signatures, at 128-bits of security strength.
          * <p>
          * This algorithm is older than the Edwards curves, and are more widely supported.
          */
         ecp256("EC", new ECGenParameterSpec("secp256r1"), "SHA256withECDSA"),
         /**
          * The NIST P-384 elliptic curve algorithm, offer fast key generation, signing, and verification,
          * with small keys and signatures, at 192-bits of security strength.
          * <p>
          * This algorithm is older than the Edwards curves, and are more widely supported.
          */
         ecp384("EC", new ECGenParameterSpec("secp384r1"), "SHA384withECDSA"),
         /**
          * The 2048-bit RSA algorithm offer roughly 112-bits of security strength, at the cost of large keys
          * and slightly expensive key generation.
          * <p>
          * This algorithm enjoy the widest support and compatibility, though.
          */
         rsa2048("RSA", new RSAKeyGenParameterSpec(2048, RSAKeyGenParameterSpec.F4), "SHA256withRSA"),
         /**
          * The 3072-bit RSA algorithm offer roughly 128-bits of security strength, at the cost of large keys
          * and fairly expensive key generation.
          * <p>
          * RSA enjoy pretty wide compatibility, though not all systems support keys this large.
          */
         rsa3072("RSA", new RSAKeyGenParameterSpec(3072, RSAKeyGenParameterSpec.F4), "SHA256withRSA"),
         /**
          * The 4096-bit RSA algorithm offer roughly greater than 128-bits of security strength,
          * at the cost of large keys and very expensive key generation.
          * <p>
          * RSA enjoy pretty wide compatibility, though not all systems support keys this large.
          */
         rsa4096("RSA", new RSAKeyGenParameterSpec(4096, RSAKeyGenParameterSpec.F4), "SHA384withRSA"),
         /**
          * The 8192-bit RSA algorithm offer roughly greater than 192-bits of security strength,
          * at the cost of very large keys and extremely expensive key generation.
          * <p>
          * RSA enjoy pretty wide compatibility, though not all systems support keys this large.
          */
         rsa8192("RSA", new RSAKeyGenParameterSpec(8192, RSAKeyGenParameterSpec.F4), "SHA384withRSA"),
         /**
          * The Ed25519 algorithm offer fast key generation, signing, and verification,
          * with very small keys and signatures, at 128-bits of security strength.
          * <p>
          * This algorithm was added in Java 15, and may not be supported everywhere.
          */
         ed25519("Ed25519", namedParameterSpec("Ed25519"), "Ed25519"),
         /**
          * The Ed448 algorithm offer fast key generation, signing, and verification,
          * with small keys and signatures, at 224-bits of security strength.
          * <p>
          * This algorithm was added in Java 15, and may not be supported everywhere.
          */
         ed448("Ed448", namedParameterSpec("Ed448"), "Ed448"),
         /**
          * The ML-DSA-44 algorithm is the NIST FIPS 204 version of the post-quantum Dilithium algorithm.
          * It has 128-bits of classical security strength, and is claimed to meet NIST Level 2
          * quantum security strength (equivalent to finding a SHA-256 collision).
          * <p>
          * This algorithm was added in Java 24, and may not be supported everywhere.
          */
         mlDsa44("ML-DSA", namedParameterSpec("ML-DSA-44"), "ML-DSA-44"),
         /**
          * The ML-DSA-65 algorithm is the NIST FIPS 204 version of the post-quantum Dilithium algorithm.
          * It has 192-bits of classical security strength, and is claimed to meet NIST Level 3
          * quantum security strength (equivalent to finding the key for an AES-192 block).
          * <p>
          * This algorithm was added in Java 24, and may not be supported everywhere.
          */
         mlDsa65("ML-DSA", namedParameterSpec("ML-DSA-65"), "ML-DSA-65"),
         /**
          * The ML-DSA-87 algorithm is the NIST FIPS 204 version of the post-quantum Dilithium algorithm.
          * It has 256-bits of classical security strength, and is claimed to meet NIST Level 5
          * quantum security strength (equivalent to finding the key for an AES-256 block).
          * <p>
          * This algorithm was added in Java 24, and may not be supported everywhere.
          */
         mlDsa87("ML-DSA", namedParameterSpec("ML-DSA-87"), "ML-DSA-87");
 
         final String keyType;
         final AlgorithmParameterSpec parameterSpec;
         final String signatureType;
 
         Algorithm(String keyType, AlgorithmParameterSpec parameterSpec, String signatureType) {
             this.keyType = keyType;
             this.parameterSpec = parameterSpec;
             this.signatureType = signatureType;
         }
 
         private static AlgorithmParameterSpec namedParameterSpec(String name) {
             try {
                 Class<?> cls = Class.forName("java.security.spec.NamedParameterSpec");
                 return (AlgorithmParameterSpec) cls.getConstructor(String.class).newInstance(name);
             } catch (Exception e) {
                 if ("Ed25519".equals(name)) {
                     return new EdDSAParameterSpec(EdDSAParameterSpec.Ed25519);
                 }
                 if ("Ed448".equals(name)) {
                     return new EdDSAParameterSpec(EdDSAParameterSpec.Ed448);
                 }
                 return UNSUPPORTED_SPEC;
             }
         }
 
         /**
          * Generate a new {@link KeyPair} using this algorithm, and the given {@link SecureRandom} generator.
          * @param secureRandom The {@link SecureRandom} generator to use, not {@code null}.
          * @return The generated {@link KeyPair}.
          * @throws GeneralSecurityException if the key pair cannot be generated using this algorithm for some reason.
          * @throws UnsupportedOperationException if this algorithm is not support in the current JVM.
          */
         public KeyPair generateKeyPair(SecureRandom secureRandom)
                 throws GeneralSecurityException {
             requireNonNull(secureRandom, "secureRandom");
 
             if (parameterSpec == UNSUPPORTED_SPEC) {
                 throw new UnsupportedOperationException("This algorithm is not supported: " + this);
             }
             if (this == mlDsa44 || this == mlDsa65 || this == mlDsa87) {
                 return genMlDsaKeyPair(secureRandom);
             }
             return genKeyPair(secureRandom);
         }
 
         private KeyPair genMlDsaKeyPair(SecureRandom secureRandom) throws GeneralSecurityException {
             final byte[] seed = new byte[32];
             KeyPair keyPair = genKeyPair(new SecureRandom() {
                 @Override
                 public void nextBytes(byte[] bytes) {
                     assert bytes.length == 32;
                     secureRandom.nextBytes(bytes);
                     System.arraycopy(bytes, 0, seed, 0, seed.length);
                 }
             });
             return new KeyPair(keyPair.getPublic(), new MLDSASeedPrivateKey(keyPair.getPrivate(), this, seed));
         }
 
         private KeyPair genKeyPair(SecureRandom secureRandom) throws GeneralSecurityException {
             KeyPairGenerator keyGen = Algorithms.keyPairGenerator(keyType, parameterSpec, secureRandom);
             return keyGen.generateKeyPair();
         }
 
         /**
          * Tell whether this algorithm is supported in the current JVM.
          * @return {@code true} if this algorithm is supported.
          */
         public boolean isSupported() {
             return parameterSpec != UNSUPPORTED_SPEC;
         }
     }
 
     /**
      * The key usage field specify what the certificate and key is allowed to be used for.
      * <p>
      * These key usages are specified by the X.509 standard, and some of them are deprecated.
      * <p>
      * See the {@link ExtendedKeyUsage} for other commonly used key usage extensions.
      * <p>
      * See ITU-T X.509 (10/2019) section 9.2.2.3 for the precise meaning of these usages.
      */
     public enum KeyUsage {
         /**
          * For verifying digital signatures, for entity authentication,
          * for entity authentication, or for integrity verification.
          */
         digitalSignature(0),
         /**
          * This key usage is deprecated by X.509, and commitment may instead be derived from the actual use of the keys.
          * <p>
          * For verifying digital signatures that imply the signer has "committed" to the
          * content being signed. This does not imply any specific policy or review on part of the signer, however.
          */
         contentCommitment(1),
         /**
          * For enciphering keys or other security information.
          */
         keyEncipherment(2),
         /**
          * For enciphering user data, but not keys or security information.
          */
         dataEncipherment(3),
         /**
          * For use in public key agreement.
          */
         keyAgreement(4),
         /**
          * For verifying the Certificate Authority's signature on a public-key certificate.
          * <p>
          * This implies {@link #digitalSignature} and {@link #contentCommitment}, so they do not need to be specified
          * separately.
          */
         keyCertSign(5),
         /**
          * For verifying the Certificate Authority's signature on a Certificate Revocation List.
          * <p>
          * This implies {@link #digitalSignature} and {@link #contentCommitment}, so they do not need to be specified
          * separately.
          */
         cRLSign(6),
         /**
          * For use with {@link #keyAgreement} to limit the key to enciphering only.
          * <p>
          * The meaning of this without the {@link #keyAgreement} bit set is unspecified.
          */
         encipherOnly(7),
         /**
          * For use with {@link #keyAgreement} to limit the key to deciphering only.
          * <p>
          * The meaning of this without the {@link #keyAgreement} bit set is unspecified.
          */
         decipherOnly(8);
 
         private final int bitId;
 
         KeyUsage(int bitId) {
             this.bitId = bitId;
         }
     }
 
     /**
      * The extended key usage field specify what the certificate and key is allowed to be used for.
      * <p>
      * A certificate can have many key usages. For instance, some certificates support both client and server usage
      * for TLS connections.
      * <p>
      * The key usage must be checked by the opposing peer receiving the certificate, and reject certificates that do
      * not permit the given usage.
      * <p>
      * For instance, if a TLS client connects to a server that presents a certificate without the
      * {@linkplain #PKIX_KP_SERVER_AUTH server-authentication} usage, then the client must reject the server
      * certificate as invalid.
      */
     public enum ExtendedKeyUsage {
         /**
          * The certificate can be used on the server-side of a TLS connection.
          */
         PKIX_KP_SERVER_AUTH(OID_PKIX_KP_SERVER_AUTH),
         /**
          * The certificate can be used on the client-side of a TLS connection.
          */
         PKIX_KP_CLIENT_AUTH(OID_PKIX_KP_CLIENT_AUTH),
         /**
          * The certificate can be used for code signing.
          */
         PKIX_KP_CODE_SIGNING(OID_PKIX_KP_CODE_SIGNING),
         /**
          * The certificate can be used for protecting email.
          */
         PKIX_KP_EMAIL_PROTECTION(OID_PKIX_KP_EMAIL_PROTECTION),
         /**
          * The certificate can be used for time-stamping.
          */
         PKIX_KP_TIME_STAMPING(OID_PKIX_KP_TIME_STAMPING),
         /**
          * The certificate can be used to sign OCSP replies.
          */
         PKIX_KP_OCSP_SIGNING(OID_PKIX_KP_OCSP_SIGNING),
         /**
          * The certificate can be used for Kerberos client authentication.
          */
         KERBEROS_KEY_PURPOSE_CLIENT_AUTH(OID_KERBEROS_KEY_PURPOSE_CLIENT_AUTH),
         /**
          * The certificate can be used for Microsoft smartcard logins.
          */
         MICROSOFT_SMARTCARD_LOGIN(OID_MICROSOFT_SMARTCARD_LOGIN);
 
         private final String oid;
 
         ExtendedKeyUsage(String oid) {
             this.oid = oid;
         }
 
         public String getOid() {
             return oid;
         }
     }
 
     @FunctionalInterface
     private interface BuilderCallback {
         void modify(ExtensionsGenerator builder) throws Exception;
     }
 
     private static final class SecureRandomHolder {
         private static final SecureRandom RANDOM = new SecureRandom();
     }
 }