24935862995

Committed 25 Apr 2026 04:54PM UTC coverage: 56.537%. First build

Build # 24935862995

Build Type

Pull #7605

github

Committed by

web-flow

Commit Message

Merge b6bd320ea into 7922186b4

Pull Request Pull Request #7605: fix: allow signing for legacy certificates missing CRL metadata (fixes #7597)

Coverage Stats

47 of 53 new or added lines in 2 files covered. (88.68%)

10599 of 18747 relevant lines covered (56.54%)

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67.91

/lib/Handler/CertificateEngine/AEngineHandler.php

<?php

declare(strict_types=1);
/**
 * SPDX-FileCopyrightText: 2020-2024 LibreCode coop and contributors
 * SPDX-License-Identifier: AGPL-3.0-or-later
 */

namespace OCA\Libresign\Handler\CertificateEngine;

use OCA\Libresign\AppInfo\Application;
use OCA\Libresign\Enum\CrlValidationStatus;
use OCA\Libresign\Exception\EmptyCertificateException;
use OCA\Libresign\Exception\InvalidPasswordException;
use OCA\Libresign\Exception\LibresignException;
use OCA\Libresign\Helper\ConfigureCheckHelper;
use OCA\Libresign\Helper\MagicGetterSetterTrait;
use OCA\Libresign\Service\CaIdentifierService;
use OCA\Libresign\Service\CertificatePolicyService;
use OCA\Libresign\Service\Crl\CrlDistributionPointsExtractor;
use OCA\Libresign\Service\Crl\CrlRevocationChecker;
use OCP\Files\AppData\IAppDataFactory;
use OCP\Files\IAppData;
use OCP\Files\SimpleFS\ISimpleFolder;
use OCP\IAppConfig;
use OCP\IConfig;
use OCP\IDateTimeFormatter;
use OCP\ITempManager;
use OCP\IURLGenerator;
use OpenSSLAsymmetricKey;
use OpenSSLCertificate;
use Psr\Log\LoggerInterface;
use ReflectionClass;

/**
 * @method IEngineHandler setPassword(string $password)
 * @method string getPassword()
 * @method IEngineHandler setCommonName(string $commonName)
 * @method string getCommonName()
 * @method IEngineHandler setHosts(array $hosts)
 * @method array getHosts()
 * @method IEngineHandler setFriendlyName(string $friendlyName)
 * @method string getFriendlyName()
 * @method IEngineHandler setCountry(string $country)
 * @method string getCountry()
 * @method IEngineHandler setState(string $state)
 * @method string getState()
 * @method IEngineHandler setLocality(string $locality)
 * @method string getLocality()
 * @method IEngineHandler setOrganization(string $organization)
 * @method string getOrganization()
 * @method IEngineHandler setOrganizationalUnit(array $organizationalUnit)
 * @method array getOrganizationalUnit()
 * @method IEngineHandler setUID(string $UID)
 * @method string getName()
 */
abstract class AEngineHandler implements IEngineHandler {
        use MagicGetterSetterTrait;
        use OrderCertificatesTrait;

        protected string $commonName = '';
        protected array $hosts = [];
        protected string $friendlyName = '';
        protected string $country = '';
        protected string $state = '';
        protected string $locality = '';
        protected string $organization = '';
        protected array $organizationalUnit = [];
        protected string $UID = '';
        private ?int $leafExpiryOverrideInDays = null;
        protected string $password = '';
        protected string $configPath = '';
        protected string $engine = '';
        protected string $certificate = '';
        protected string $currentCaId = '';
        protected IAppData $appData;
        private CrlDistributionPointsExtractor $crlDistributionPointsExtractor;

        public function __construct(
                protected IConfig $config,
                protected IAppConfig $appConfig,
                protected IAppDataFactory $appDataFactory,
                protected IDateTimeFormatter $dateTimeFormatter,
                protected ITempManager $tempManager,
                protected CertificatePolicyService $certificatePolicyService,
                protected IURLGenerator $urlGenerator,
                protected CaIdentifierService $caIdentifierService,
                protected LoggerInterface $logger,
                private CrlRevocationChecker $crlRevocationChecker,
                ?CrlDistributionPointsExtractor $crlDistributionPointsExtractor = null,
        ) {
                $this->appData = $appDataFactory->get('libresign');
                $this->crlDistributionPointsExtractor = $crlDistributionPointsExtractor ?? new CrlDistributionPointsExtractor();
        }

        protected function exportToPkcs12(
                OpenSSLCertificate|string $certificate,
                OpenSSLAsymmetricKey|OpenSSLCertificate|string $privateKey,
                array $options = [],
        ): string {
                if (empty($certificate) || empty($privateKey)) {
                        throw new EmptyCertificateException();
                }
                $certContent = null;
                try {
                        openssl_pkcs12_export(
                                $certificate,
                                $certContent,
                                $privateKey,
                                $this->getPassword(),
                                $options,
                        );
                        if (!$certContent) {
                                throw new \Exception();
                        }
                } catch (\Throwable) {
                        throw new LibresignException('Error while creating certificate file', 500);
                }

                return $certContent;
        }

        #[\Override]
        public function updatePassword(string $certificate, string $currentPrivateKey, string $newPrivateKey): string {
                if (empty($certificate) || empty($currentPrivateKey) || empty($newPrivateKey)) {
                        throw new EmptyCertificateException();
                }
                $certContent = $this->opensslPkcs12Read($certificate, $currentPrivateKey);
                $this->setPassword($newPrivateKey);
                $certContent = self::exportToPkcs12($certContent['cert'], $certContent['pkey']);
                return $certContent;
        }

        #[\Override]
        public function readCertificate(string $certificate, string $privateKey): array {
                if (empty($certificate) || empty($privateKey)) {
                        throw new EmptyCertificateException();
                }
                $certContent = $this->opensslPkcs12Read($certificate, $privateKey);

                $return = $this->parseX509($certContent['cert']);
                if (isset($certContent['extracerts'])) {
                        foreach ($certContent['extracerts'] as $extraCert) {
                                $return['extracerts'][] = $this->parseX509($extraCert);
                        }
                        $return['extracerts'] = $this->orderCertificates($return['extracerts']);
                }
                return $return;
        }

        public function getCaId(): string {
                $caId = $this->caIdentifierService->getCaId();
                if (empty($caId)) {
                        $this->appConfig->clearCache(true);
                        $caId = $this->caIdentifierService->getCaId() ?: $this->caIdentifierService->generateCaId($this->getName());
                }
                return $caId;
        }

        #[\Override]
        public function parseCertificate(string $certificate): array {
                return $this->parseX509($certificate);
        }

        private function parseX509(string $x509): array {
                $parsed = openssl_x509_parse(openssl_x509_read($x509));

                $return = self::convertArrayToUtf8($parsed);

                foreach (['subject', 'issuer'] as $actor) {
                        foreach ($return[$actor] as $part => $value) {
                                if (is_string($value) && str_contains($value, ', ')) {
                                        $return[$actor][$part] = explode(', ', $value);
                                } else {
                                        $return[$actor][$part] = $value;
                                }
                        }
                }

                $return['valid_from'] = $this->dateTimeFormatter->formatDateTime($parsed['validFrom_time_t']);
                $return['valid_to'] = $this->dateTimeFormatter->formatDateTime($parsed['validTo_time_t']);

                $this->addCrlValidationInfo($return, $x509);

                return $return;
        }

        private function addCrlValidationInfo(array &$certData, string $certPem): void {
                $extensions = $certData['extensions'] ?? [];
                if (is_array($extensions)) {
                        ['hasExtension' => $hasCrlExtension, 'urls' => $extractedUrls] = $this->crlDistributionPointsExtractor->extractFromExtensions($extensions);
                        if ($hasCrlExtension) {
                                $certData['crl_urls'] = $extractedUrls;
                                if (empty($extractedUrls)) {
                                        $certData['crl_validation'] = CrlValidationStatus::NO_URLS;
                                        return;
                                }

                                $crlDetails = $this->crlRevocationChecker->validate($extractedUrls, $certPem);
                                $certData['crl_validation'] = $crlDetails['status'];
                                if (!empty($crlDetails['revoked_at'])) {
                                        $certData['crl_revoked_at'] = $crlDetails['revoked_at'];
                                }
                                return;
                        }
                }

                $externalValidationEnabled = $this->appConfig->getValueBool(Application::APP_ID, 'crl_external_validation_enabled', true);
                $certData['crl_validation'] = $externalValidationEnabled
                        ? CrlValidationStatus::MISSING
                        : CrlValidationStatus::DISABLED;
                $certData['crl_urls'] = [];
        }

        private static function convertArrayToUtf8($array) {
                foreach ($array as $key => $value) {
                        if (is_array($value)) {
                                $array[$key] = self::convertArrayToUtf8($value);
                        } elseif (is_string($value)) {
                                $array[$key] = mb_convert_encoding($value, 'UTF-8', 'UTF-8');
                        }
                }
                return $array;
        }

        public function opensslPkcs12Read(string &$certificate, string $privateKey): array {
                openssl_pkcs12_read($certificate, $certContent, $privateKey);
                if (!empty($certContent)) {
                        return $certContent;
                }
                /**
                 * Reference:
                 *
                 * https://github.com/php/php-src/issues/12128
                 * https://www.php.net/manual/en/function.openssl-pkcs12-read.php#128992
                 */
                $msg = openssl_error_string();
                if ($msg === 'error:0308010C:digital envelope routines::unsupported') {
                        $tempPassword = $this->tempManager->getTemporaryFile();
                        $tempEncriptedOriginal = $this->tempManager->getTemporaryFile();
                        $tempEncriptedRepacked = $this->tempManager->getTemporaryFile();
                        $tempDecrypted = $this->tempManager->getTemporaryFile();
                        file_put_contents($tempPassword, $privateKey);
                        file_put_contents($tempEncriptedOriginal, $certificate);
                        shell_exec(<<<REPACK_COMMAND
                                cat $tempPassword | openssl pkcs12 -legacy -in $tempEncriptedOriginal -nodes -out $tempDecrypted -passin stdin &&
                                cat $tempPassword | openssl pkcs12 -in $tempDecrypted -export -out $tempEncriptedRepacked -passout stdin
                                REPACK_COMMAND
                        );
                        $certificateRepacked = file_get_contents($tempEncriptedRepacked);
                        openssl_pkcs12_read($certificateRepacked, $certContent, $privateKey);
                        if (!empty($certContent)) {
                                $certificate = $certificateRepacked;
                                return $certContent;
                        }
                }
                throw new InvalidPasswordException();
        }

        /**
         * @param (int|string) $name
         *
         * @psalm-param array-key $name
         */
        public function translateToLong($name): string {
                return match ($name) {
                        'CN' => 'CommonName',
                        'C' => 'Country',
                        'ST' => 'State',
                        'L' => 'Locality',
                        'O' => 'Organization',
                        'OU' => 'OrganizationalUnit',
                        'UID' => 'UserIdentifier',
                        default => '',
                };
        }

        #[\Override]
        public function setEngine(string $engine): void {
                $this->appConfig->setValueString(Application::APP_ID, 'certificate_engine', $engine);
                $this->engine = $engine;
                $this->configureIdentifyMethodsForEngine($engine);
        }

        /**
         * Configure identification methods based on the certificate engine.
         *
         * When the engine is set to 'none', only the 'account' identification method
         * is allowed. This is because:
         * - The 'none' engine doesn't generate digital certificates
         * - Without certificates, only basic password authentication is viable
         * - The 'account' method ensures users authenticate with their Nextcloud credentials
         *
         * For other engines (openssl, cfssl, java), the identification methods remain
         * unchanged to preserve existing configurations.
         *
         * @param string $engine The certificate engine name (i.e. 'none', 'openssl', 'cfssl')
         */
        private function configureIdentifyMethodsForEngine(string $engine): void {
                if ($engine !== 'none') {
                        return;
                }

                $config = [[
                        'name' => 'account',
                        'enabled' => true,
                        'mandatory' => true,
                ]];
                $this->appConfig->setValueArray(Application::APP_ID, 'identify_methods', $config);
        }

        #[\Override]
        public function getEngine(): string {
                if ($this->engine) {
                        return $this->engine;
                }
                $this->engine = $this->appConfig->getValueString(Application::APP_ID, 'certificate_engine', 'openssl');
                return $this->engine;
        }

        #[\Override]
        public function populateInstance(array $rootCert): IEngineHandler {
                if (empty($rootCert)) {
                        $rootCert = $this->appConfig->getValueArray(Application::APP_ID, 'rootCert');
                }
                if (!$rootCert) {
                        return $this;
                }
                if (!empty($rootCert['names'])) {
                        foreach ($rootCert['names'] as $id => $customName) {
                                $longCustomName = $this->translateToLong($id);
                                // Prevent to save a property that don't exists
                                if (!property_exists($this, lcfirst($longCustomName))) {
                                        continue;
                                }
                                $this->{'set' . ucfirst($longCustomName)}($customName['value']);
                        }
                }
                if (!$this->getCommonName()) {
                        $this->setCommonName($rootCert['commonName']);
                }
                return $this;
        }

        #[\Override]
        public function getCurrentConfigPath(): string {
                if ($this->configPath) {
                        return $this->configPath;
                }

                $customConfigPath = $this->appConfig->getValueString(Application::APP_ID, 'config_path');
                if ($customConfigPath && is_dir($customConfigPath)) {
                        $this->configPath = $customConfigPath;
                        return $this->configPath;
                }

                $this->configPath = $this->initializePkiConfigPath();
                if (!empty($this->configPath)) {
                        $this->appConfig->setValueString(Application::APP_ID, 'config_path', $this->configPath);
                }
                return $this->configPath;
        }

        #[\Override]
        public function getConfigPathByParams(string $instanceId, int $generation): string {
                $engineName = $this->getName();

                $pkiDirName = $this->caIdentifierService->generatePkiDirectoryNameFromParams($instanceId, $generation, $engineName);
                $dataDir = $this->config->getSystemValue('datadirectory', \OC::$SERVERROOT . '/data/');
                $systemInstanceId = $this->config->getSystemValue('instanceid');
                $pkiPath = $dataDir . '/appdata_' . $systemInstanceId . '/libresign/' . $pkiDirName;

                if (!is_dir($pkiPath)) {
                        throw new \RuntimeException("Config path does not exist for instanceId: {$instanceId}, generation: {$generation}");
                }

                return $pkiPath;
        }

        private function initializePkiConfigPath(): string {
                $caId = $this->getCaId();
                if (empty($caId)) {
                        return '';
                }
                $pkiDirName = $this->caIdentifierService->generatePkiDirectoryName($caId);
                $dataDir = $this->config->getSystemValue('datadirectory', \OC::$SERVERROOT . '/data/');
                $systemInstanceId = $this->config->getSystemValue('instanceid');
                $pkiPath = $dataDir . '/appdata_' . $systemInstanceId . '/libresign/' . $pkiDirName;

                if (!is_dir($pkiPath)) {
                        $this->createDirectoryWithCorrectOwnership($pkiPath);
                }

                return $pkiPath;
        }

        private function createDirectoryWithCorrectOwnership(string $path): void {
                $ownerInfo = $this->getFilesOwnerInfo();
                $fullCommand = 'mkdir -p ' . escapeshellarg($path);

                if (posix_getuid() !== $ownerInfo['uid']) {
                        $fullCommand = 'runuser -u ' . $ownerInfo['name'] . ' -- ' . $fullCommand;
                }

                exec($fullCommand);
        }

        private function getFilesOwnerInfo(): array {
                $currentFile = realpath(__DIR__);
                $owner = fileowner($currentFile);
                if ($owner === false) {
                        throw new \RuntimeException('Unable to get file information');
                }
                $ownerInfo = posix_getpwuid($owner);
                if ($ownerInfo === false) {
                        throw new \RuntimeException('Unable to get file owner information');
                }

                return $ownerInfo;
        }

        /**
         * @todo check a best solution to don't use reflection
         */
        private function getInternalPathOfFolder(ISimpleFolder $node): string {
                $reflection = new \ReflectionClass($node);
                $reflectionProperty = $reflection->getProperty('folder');
                $folder = $reflectionProperty->getValue($node);
                $path = $folder->getInternalPath();
                return $path;
        }

        #[\Override]
        public function setConfigPath(string $configPath): IEngineHandler {
                if (!$configPath) {
                        $this->appConfig->deleteKey(Application::APP_ID, 'config_path');
                } else {
                        if (!is_dir($configPath)) {
                                mkdir(
                                        directory: $configPath,
                                        recursive: true,
                                );
                        }
                        $this->appConfig->setValueString(Application::APP_ID, 'config_path', $configPath);
                }
                $this->configPath = $configPath;
                return $this;
        }

        public function getName(): string {
                $reflect = new ReflectionClass($this);
                $className = $reflect->getShortName();
                $name = strtolower(substr($className, 0, -7));
                return $name;
        }

        protected function getNames(): array {
                $names = [
                        'C' => $this->getCountry(),
                        'ST' => $this->getState(),
                        'L' => $this->getLocality(),
                        'O' => $this->getOrganization(),
                        'OU' => $this->getOrganizationalUnit(),
                ];
                if ($uid = $this->getUID()) {
                        $names['UID'] = $uid;
                }
                $names = array_filter($names, fn ($v) => !empty($v));
                return $names;
        }

        public function getUID(): string {
                return str_replace(' ', '+', $this->UID);
        }

        #[\Override]
        public function getLeafExpiryInDays(): int {
                if ($this->leafExpiryOverrideInDays !== null) {
                        return $this->leafExpiryOverrideInDays;
                }
                $exp = $this->appConfig->getValueInt(Application::APP_ID, 'expiry_in_days', 365);
                return $exp > 0 ? $exp : 365;
        }

        #[\Override]
        public function setLeafExpiryOverrideInDays(?int $days): self {
                $this->leafExpiryOverrideInDays = ($days !== null && $days > 0) ? $days : null;
                return $this;
        }

        #[\Override]
        public function getCaExpiryInDays(): int {
                $exp = $this->appConfig->getValueInt(Application::APP_ID, 'ca_expiry_in_days', 3650); // 10 years
                return $exp > 0 ? $exp : 3650;
        }

        private function getCertificatePolicy(): array {
                $return = ['policySection' => []];
                $oid = $this->certificatePolicyService->getOid();
                $cps = $this->certificatePolicyService->getCps();
                if ($oid && $cps) {
                        $return['policySection'][] = [
                                'OID' => $oid,
                                'CPS' => $cps,
                        ];
                }
                return $return;
        }

        abstract protected function getConfigureCheckResourceName(): string;

        abstract protected function getCertificateRegenerationTip(): string;

        abstract protected function getEngineSpecificChecks(): array;

        abstract protected function getSetupSuccessMessage(): string;

        abstract protected function getSetupErrorMessage(): string;

        abstract protected function getSetupErrorTip(): string;

        #[\Override]
        public function configureCheck(): array {
                $checks = $this->getEngineSpecificChecks();

                if (!$this->isSetupOk()) {
                        return array_merge($checks, [
                                (new ConfigureCheckHelper())
                                        ->setErrorMessage($this->getSetupErrorMessage())
                                        ->setResource($this->getConfigureCheckResourceName())
                                        ->setTip($this->getSetupErrorTip())
                        ]);
                }

                $checks[] = (new ConfigureCheckHelper())
                        ->setSuccessMessage($this->getSetupSuccessMessage())
                        ->setResource($this->getConfigureCheckResourceName());

                $modernFeaturesCheck = $this->checkRootCertificateModernFeatures();
                if ($modernFeaturesCheck) {
                        $checks[] = $modernFeaturesCheck;
                }

                $expiryCheck = $this->checkRootCertificateExpiry();
                if ($expiryCheck) {
                        $checks[] = $expiryCheck;
                }

                return $checks;
        }

        protected function checkRootCertificateModernFeatures(): ?ConfigureCheckHelper {
                $configPath = $this->getCurrentConfigPath();
                $caCertPath = $configPath . DIRECTORY_SEPARATOR . 'ca.pem';

                try {
                        $certContent = file_get_contents($caCertPath);
                        if (!$certContent) {
                                return (new ConfigureCheckHelper())
                                        ->setErrorMessage('Failed to read root certificate file')
                                        ->setResource($this->getConfigureCheckResourceName())
                                        ->setTip('Check file permissions and disk space');
                        }

                        $x509Resource = openssl_x509_read($certContent);
                        if (!$x509Resource) {
                                return (new ConfigureCheckHelper())
                                        ->setErrorMessage('Failed to parse root certificate')
                                        ->setResource($this->getConfigureCheckResourceName())
                                        ->setTip('Root certificate file may be corrupted or invalid');
                        }

                        $parsed = openssl_x509_parse($x509Resource);
                        if (!$parsed) {
                                return (new ConfigureCheckHelper())
                                        ->setErrorMessage('Failed to extract root certificate information')
                                        ->setResource($this->getConfigureCheckResourceName())
                                        ->setTip('Root certificate may be in an unsupported format');
                        }

                        $criticalIssues = [];
                        $minorIssues = [];

                        if (isset($parsed['serialNumber'])) {
                                $serialNumber = $parsed['serialNumber'];
                                $serialDecimal = hexdec($serialNumber);
                                if ($serialDecimal <= 1) {
                                        $minorIssues[] = 'Serial number is simple (zero or one)';
                                }
                        } else {
                                $criticalIssues[] = 'Serial number is missing';
                        }

                        $missingExtensions = [];
                        if (!isset($parsed['extensions']['subjectKeyIdentifier'])) {
                                $missingExtensions[] = 'Subject Key Identifier (SKI)';
                        }

                        $isSelfSigned = (isset($parsed['issuer']) && isset($parsed['subject'])
                                                        && $parsed['issuer'] === $parsed['subject']);

                        /**
                         * @todo workarround for missing AKI at certificates generated by CFSSL.
                         *
                         * CFSSL does not add Authority Key Identifier (AKI) to self-signed root certificates.
                         */
                        if (!$isSelfSigned && !isset($parsed['extensions']['authorityKeyIdentifier'])) {
                                $missingExtensions[] = 'Authority Key Identifier (AKI)';
                        }

                        if (!isset($parsed['extensions']['crlDistributionPoints'])) {
                                $missingExtensions[] = 'CRL Distribution Points';
                        }

                        if (!empty($missingExtensions)) {
                                $extensionsList = implode(', ', $missingExtensions);
                                $minorIssues[] = "Missing modern extensions: {$extensionsList}";
                        }

                        $hasLibresignCaUuid = $this->validateLibresignCaUuidInCertificate($parsed);
                        if (!$hasLibresignCaUuid) {
                                $minorIssues[] = 'LibreSign CA UUID not found in Organizational Unit';
                        }

                        if (!empty($criticalIssues)) {
                                $issuesList = implode(', ', $criticalIssues);
                                return (new ConfigureCheckHelper())
                                        ->setErrorMessage("Root certificate has critical issues: {$issuesList}")
                                        ->setResource($this->getConfigureCheckResourceName())
                                        ->setTip($this->getCertificateRegenerationTip());
                        }

                        if (!empty($minorIssues)) {
                                $issuesList = implode(', ', $minorIssues);
                                return (new ConfigureCheckHelper())
                                        ->setInfoMessage("Root certificate could benefit from modern features: {$issuesList}")
                                        ->setResource($this->getConfigureCheckResourceName())
                                        ->setTip($this->getCertificateRegenerationTip() . ' (recommended but not required)');
                        }

                        return null;

                } catch (\Exception $e) {
                        return (new ConfigureCheckHelper())
                                ->setErrorMessage('Failed to analyze root certificate: ' . $e->getMessage())
                                ->setResource($this->getConfigureCheckResourceName())
                                ->setTip('Check if the root certificate file is valid');
                }
        }

        private function validateLibresignCaUuidInCertificate(array $parsed): bool {
                if (!isset($parsed['subject']['OU'])) {
                        return false;
                }

                $instanceId = $this->getLibreSignInstanceId();
                if (empty($instanceId)) {
                        return false;
                }

                $organizationalUnits = $parsed['subject']['OU'];

                if (is_string($organizationalUnits)) {
                        if (str_contains($organizationalUnits, ', ')) {
                                $organizationalUnits = explode(', ', $organizationalUnits);
                        } else {
                                $organizationalUnits = [$organizationalUnits];
                        }
                }

                foreach ($organizationalUnits as $ou) {
                        $ou = trim($ou);
                        if ($this->caIdentifierService->isValidCaId($ou, $instanceId)) {
                                return true;
                        }
                }

                return false;
        }

        private function getLibreSignInstanceId(): string {
                $instanceId = $this->appConfig->getValueString(Application::APP_ID, 'instance_id', '');
                if (strlen($instanceId) === 10) {
                        return $instanceId;
                }
                return '';
        }

        private function calculateRemainingDays(int $validToTimestamp): int {
                $secondsPerDay = 60 * 60 * 24;
                $remainingSeconds = $validToTimestamp - time();
                return (int)ceil($remainingSeconds / $secondsPerDay);
        }

        protected function checkRootCertificateExpiry(): ?ConfigureCheckHelper {
                $configPath = $this->getCurrentConfigPath();
                $caCertPath = $configPath . DIRECTORY_SEPARATOR . 'ca.pem';

                if (!file_exists($caCertPath)) {
                        return null;
                }

                $certContent = file_get_contents($caCertPath);
                if (!$certContent) {
                        return null;
                }

                $x509Resource = openssl_x509_read($certContent);
                if (!$x509Resource) {
                        return null;
                }

                $parsed = openssl_x509_parse($x509Resource);
                if (!$parsed) {
                        return null;
                }

                $remainingDays = $this->calculateRemainingDays($parsed['validTo_time_t']);
                $leafExpiryDays = $this->getLeafExpiryInDays();

                if ($remainingDays < 0) {
                        return (new ConfigureCheckHelper())
                                ->setErrorMessage('Root certificate has expired')
                                ->setResource($this->getConfigureCheckResourceName())
                                ->setTip($this->getCertificateRegenerationTip() . ' URGENT: Certificate is expired!');
                }

                if ($remainingDays <= 7) {
                        return (new ConfigureCheckHelper())
                                ->setErrorMessage("Root certificate expires in {$remainingDays} days")
                                ->setResource($this->getConfigureCheckResourceName())
                                ->setTip($this->getCertificateRegenerationTip() . ' URGENT: Renew immediately!');
                }

                if ($remainingDays <= 30) {
                        return (new ConfigureCheckHelper())
                                ->setErrorMessage("Root certificate expires in {$remainingDays} days")
                                ->setResource($this->getConfigureCheckResourceName())
                                ->setTip($this->getCertificateRegenerationTip() . ' Renewal recommended soon.');
                }

                if ($remainingDays <= $leafExpiryDays) {
                        return (new ConfigureCheckHelper())
                                ->setInfoMessage("Root certificate expires in {$remainingDays} days (leaf validity: {$leafExpiryDays} days)")
                                ->setResource($this->getConfigureCheckResourceName())
                                ->setTip('Root certificate should be renewed to ensure it can sign CRLs for all issued leaf certificates.');
                }

                return null;
        }

        #[\Override]
        public function toArray(): array {
                $generated = $this->isSetupOk();
                $return = [
                        'configPath' => $this->getConfigPathForApi($generated),
                        'generated' => $generated,
                        'rootCert' => [
                                'commonName' => $this->getCommonName(),
                                'names' => [],
                        ],
                ];
                $return = array_merge(
                        $return,
                        $this->getCertificatePolicy(),
                );
                $names = $this->getNames();
                foreach ($names as $name => $value) {
                        $return['rootCert']['names'][] = [
                                'id' => $name,
                                'value' => $this->filterNameValue($name, $value, $generated),
                        ];
                }
                return $return;
        }

        private function getConfigPathForApi(bool $generated): string {
                return $generated ? $this->getCurrentConfigPath() : '';
        }

        private function filterNameValue(string $name, mixed $value, bool $generated): mixed {
                if ($name === 'OU' && is_array($value) && !$generated) {
                        $filtered = $this->removeCaIdFromOrganizationalUnit($value);
                        return empty($filtered) ? null : $filtered;
                }
                return $value;
        }

        private function removeCaIdFromOrganizationalUnit(array $organizationalUnits): array {
                $filtered = array_filter(
                        $organizationalUnits,
                        fn ($item) => !str_starts_with($item, 'libresign-ca-id:')
                );
                return array_values($filtered);
        }

        protected function getCrlDistributionUrl(): string {
                $caIdParsed = $this->caIdentifierService->getCaIdParsed();
                return $this->urlGenerator->linkToRouteAbsolute('libresign.crl.getRevocationList', [
                        'instanceId' => $caIdParsed['instanceId'],
                        'generation' => $caIdParsed['generation'],
                        'engineType' => $caIdParsed['engineType'],
                ]);
        }

        #[\Override]
        public function generateCrlDer(array $revokedCertificates, string $instanceId, int $generation, int $crlNumber): string {
                $configPath = $this->getConfigPathByParams($instanceId, $generation);
                $issuer = $this->loadCaIssuer($configPath);
                $signedCrl = $this->createAndSignCrl($issuer, $revokedCertificates, $crlNumber);
                $crlDerData = $this->saveCrlToDer($signedCrl, $configPath);

                return $crlDerData;
        }

        private function loadCaIssuer(string $configPath): \phpseclib3\File\X509 {
                $caCertPath = $configPath . DIRECTORY_SEPARATOR . 'ca.pem';
                $caKeyPath = $configPath . DIRECTORY_SEPARATOR . 'ca-key.pem';

                if (!file_exists($caCertPath) || !file_exists($caKeyPath)) {
                        $this->logger->error('CA certificate or private key not found', ['caCertPath' => $caCertPath, 'caKeyPath' => $caKeyPath]);
                        throw new \RuntimeException('CA certificate or private key not found. Run: occ libresign:configure:openssl');
                }

                $caCert = file_get_contents($caCertPath);
                $caKey = file_get_contents($caKeyPath);

                if (!$caCert || !$caKey) {
                        $this->logger->error('Failed to read CA certificate or private key', ['caCertPath' => $caCertPath, 'caKeyPath' => $caKeyPath]);
                        throw new \RuntimeException('Failed to read CA certificate or private key');
                }

                $issuer = new \phpseclib3\File\X509();
                $issuer->loadX509($caCert);
                $caPrivateKey = \phpseclib3\Crypt\PublicKeyLoader::load($caKey);

                if (!$caPrivateKey instanceof \phpseclib3\Crypt\Common\PrivateKey) {
                        $this->logger->error('Loaded key is not a private key', ['keyType' => get_class($caPrivateKey)]);
                        throw new \RuntimeException('Loaded key is not a private key');
                }

                $issuer->setPrivateKey($caPrivateKey);
                return $issuer;
        }

        private function createAndSignCrl(\phpseclib3\File\X509 $issuer, array $revokedCertificates, int $crlNumber): array {
                $utcZone = new \DateTimeZone('UTC');
                $crlToSign = new \phpseclib3\File\X509();
                $crlToSign->setSerialNumber((string)$crlNumber, 10);
                $crlToSign->setStartDate(new \DateTime('now', $utcZone));
                $crlToSign->setEndDate(new \DateTime('+7 days', $utcZone));

                $initialCrl = $crlToSign->signCRL($issuer, $crlToSign);
                if ($initialCrl === false) {
                        $this->logger->error('Failed to create initial CRL structure');
                        throw new \RuntimeException('Failed to create initial CRL structure');
                }

                if (!empty($revokedCertificates)) {
                        $savedCrl = $crlToSign->saveCRL($initialCrl);
                        if ($savedCrl === false) {
                                $this->logger->error('Failed to save initial CRL structure');
                                throw new \RuntimeException('Failed to save initial CRL structure');
                        }

                        $crlToSign->loadCRL($savedCrl);

                        $dateFormat = 'D, d M Y H:i:s O';
                        foreach ($revokedCertificates as $cert) {
                                $serialNumber = $cert->getSerialNumber();
                                $normalizedSerial = ltrim($serialNumber, '0') ?: '0';
                                $crlToSign->revoke(
                                        new \phpseclib3\Math\BigInteger($normalizedSerial, 16),
                                        $cert->getRevokedAt()->format($dateFormat)
                                );
                        }

                        $signedCrl = $crlToSign->signCRL($issuer, $crlToSign);
                } else {
                        $signedCrl = $initialCrl;
                }

                if ($signedCrl === false) {
                        $this->logger->error('Failed to sign CRL', ['crlNumber' => $crlNumber]);
                        throw new \RuntimeException('Failed to sign CRL');
                }

                if (!isset($signedCrl['signatureAlgorithm'])) {
                        $signedCrl['signatureAlgorithm'] = ['algorithm' => 'sha256WithRSAEncryption'];
                }

                return $signedCrl;
        }

        private function saveCrlToDer(array $signedCrl, string $configPath): string {
                $crlDerPath = $configPath . DIRECTORY_SEPARATOR . 'crl.der';
                $crlToSign = new \phpseclib3\File\X509();

                $crlDerData = $crlToSign->saveCRL($signedCrl, \phpseclib3\File\X509::FORMAT_DER);

                if ($crlDerData === false) {
                        $this->logger->error('Failed to save CRL in DER format');
                        throw new \RuntimeException('Failed to save CRL in DER format');
                }

                if (file_put_contents($crlDerPath, $crlDerData) === false) {
                        $this->logger->error('Failed to write CRL DER file', ['path' => $crlDerPath]);
                        throw new \RuntimeException('Failed to write CRL DER file');
                }

                return $crlDerData;
        }

        #[\Override]
        public function validateRootCertificate(): void {
                $configPath = $this->getCurrentConfigPath();
                if (empty($configPath)) {
                        return;
                }

                if (!is_dir($configPath)) {
                        return;
                }

                $rootCertPath = $configPath . DIRECTORY_SEPARATOR . 'ca.pem';

                if (!file_exists($rootCertPath)) {
                        return;
                }

                $rootCert = file_get_contents($rootCertPath);
                if (empty($rootCert)) {
                        return;
                }

                $certificate = openssl_x509_read($rootCert);
                if ($certificate === false) {
                        throw new LibresignException('Invalid root certificate content');
                }
                $certInfo = openssl_x509_parse($certificate);
                if ($certInfo === false) {
                        throw new LibresignException('Failed to parse root certificate');
                }

                if ($this->checkCertificateRevoked($certInfo['serialNumber'])) {
                        $this->logger->error('Root certificate has been revoked', [
                                'ca_id' => $this->getCaId(),
                                'impact' => 'all_leaf_certificates_invalid',
                        ]);
                        throw new LibresignException(
                                'Root certificate has been revoked. Please contact the administrator to regenerate the signing certificate.',
                                \OC\AppFramework\Http::STATUS_PRECONDITION_FAILED
                        );
                }

                if ($certInfo['validTo_time_t'] < time()) {
                        $this->logger->error('Root certificate has expired', [
                                'ca_id' => $this->getCaId(),
                        ]);
                        throw new LibresignException(
                                'Root certificate has expired. Please contact the administrator to regenerate the signing certificate.',
                                \OC\AppFramework\Http::STATUS_PRECONDITION_FAILED
                        );
                }

                $remainingDays = $this->calculateRemainingDays($certInfo['validTo_time_t']);
                $leafExpiryDays = $this->getLeafExpiryInDays();

                if ($remainingDays <= $leafExpiryDays) {
                        $this->logger->warning('Root certificate renewal needed', [
                                'remaining_days' => $remainingDays,
                                'leaf_expiry_days' => $leafExpiryDays,
                        ]);
                }
        }

        private function checkCertificateRevoked(string $serialNumber): bool {
                try {
                        /** @var \OCA\Libresign\Service\Crl\CrlService */
                        $crlService = \OC::$server->get(\OCA\Libresign\Service\Crl\CrlService::class);
                        $status = $crlService->getCertificateStatus($serialNumber);
                        return $status['status'] === 'revoked';
                } catch (\Exception $e) {
                        $this->logger->warning('Failed to check root certificate revocation status', [
                                'error' => $e->getMessage()
                        ]);
                        return false;
                }
        }
}

LibreSign / libresign / 24935862995

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