feat: Unified keystore handling, pem bundle import & inline OpenSSL operations #19

Merged
MarkL4YG merged 4 commits from feat/unifiedKeystore into main 2024-11-24 12:50:46 +00:00
14 changed files with 499 additions and 190 deletions

View file

@ -17,10 +17,4 @@ public class AutoBootKeyStoreManagement {
) {
return new KeyStoreManager(certificateCreator, passwordProvider);
}
@Bean
@ConditionalOnMissingBean(TruststoreManager.class)
public TruststoreManager truststoreProvider() {
return new TruststoreManager();
}
}

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@ -13,8 +13,13 @@ import java.security.*;
import java.security.cert.Certificate;
import java.security.cert.CertificateException;
import java.security.cert.CertificateFactory;
import java.security.cert.X509Certificate;
import java.security.spec.PKCS8EncodedKeySpec;
import java.util.Arrays;
import java.util.Base64;
import java.util.Collection;
import java.util.Objects;
import java.util.concurrent.atomic.AtomicReference;
import lombok.RequiredArgsConstructor;
import lombok.SneakyThrows;
import lombok.extern.slf4j.Slf4j;
@ -27,25 +32,21 @@ public class KeyStoreManager {
StandardOpenOption.CREATE,
StandardOpenOption.TRUNCATE_EXISTING,
};
private final OpenSSLService certificateCreator;
private final OpenSSLService openSSLService;
private final CertificatePasswordProvider passwordProvider;
private final AtomicReference<CertificateFactory> certFactory = new AtomicReference<>();
public KeystoreUsage createKeyStore(String keyStorePassphrase, CertificateUsage... serverCerts)
throws JavaSecurityException {
try {
Path keystorePath = Files.createTempFile("keystore", ".jks");
// Load the keystore
keystorePath.toFile().deleteOnExit();
log.debug("Creating keyStore at {}", keystorePath);
KeyStore keystore = KeyStore.getInstance(KeyStore.getDefaultType());
keystore.load(null, null);
keystore.load(null, keyStorePassphrase.toCharArray());
for (CertificateUsage serverCert : serverCerts) {
PrivateKey privateKey = loadPrivateKey(
serverCert.certificateKeyPath(),
passwordProvider.getPasswordFor(serverCert.fingerprint())
);
Certificate[] certChain = loadCertificateChain(serverCert.fullchainPath());
keystore.setKeyEntry(serverCert.fingerprint(), privateKey, null, certChain);
loadPrivateKeyIntoStore(keystore, serverCert);
}
// Save the keystore
@ -58,23 +59,80 @@ public class KeyStoreManager {
}
}
@SneakyThrows
public KeystoreUsage createTruststore(String truststorePassphrase, CertificateUsage... trustedCertificates) {
return createTruststore(truststorePassphrase, Arrays.asList(trustedCertificates));
}
public KeystoreUsage createTruststore(
String truststorePassphrase,
Collection<CertificateUsage> trustedCertificates
) {
try {
Path truststorePath = Files.createTempFile("truststore", ".jks");
truststorePath.toFile().deleteOnExit();
log.debug("Creating truststore at {}", truststorePath);
KeyStore truststore = KeyStore.getInstance(KeyStore.getDefaultType());
truststore.load(null, truststorePassphrase.toCharArray());
for (CertificateUsage serverCert : trustedCertificates) {
loadPublicKeyIntoTrust(truststore, serverCert);
}
try (var outputStream = Files.newOutputStream(truststorePath, CREATE_TRUNCATE)) {
truststore.store(outputStream, truststorePassphrase.toCharArray());
}
return new KeystoreResult(truststorePath);
} catch (IOException | KeyStoreException | CertificateException | NoSuchAlgorithmException e) {
throw new IllegalStateException("Failed to create truststore!", e);
}
}
public void loadPrivateKeyIntoStore(KeyStore keyStore, CertificateUsage cert) throws KeyStoreException {
String passphrase = passwordProvider.getPasswordFor(cert.fingerprint());
var pKey = loadPrivateKey(
Objects.requireNonNull(cert.certificateKeyPath(), "Certificate does not have a key to import."),
passphrase
);
var certChain = loadCertificateChain(cert.fullchainPath());
keyStore.setKeyEntry("KEY;%s".formatted(cert.fingerprint()), pKey, null, certChain);
}
public void loadPublicKeyIntoTrust(KeyStore keyStore, CertificateUsage cert) throws KeyStoreException {
try (var inputStream = Files.newInputStream(cert.certificatePath())) {
Collection<? extends Certificate> parsedCerts = getX509Factory().generateCertificates(inputStream);
if (parsedCerts.size() != 1) {
throw new IllegalStateException(
"CertificateUsage parsed to not exactly one result! " + parsedCerts.size()
);
}
Certificate parsedCert = parsedCerts.stream().toList().getFirst();
if (!(parsedCert instanceof X509Certificate x509cert)) {
throw new IllegalStateException("CertificateUsage did not parse to X509 format??");
}
keyStore.setCertificateEntry("TRUST;%s".formatted(cert.fingerprint()), x509cert);
} catch (IOException e) {
throw new IllegalStateException("CertificateUsage could not be read??", e);
} catch (CertificateException e) {
throw new IllegalStateException("CertificateUsage is not a parsable certificate??");
}
}
@SneakyThrows
private PrivateKey loadPrivateKey(Path privateKey, String passphrase) {
String pemContent;
if (certificateCreator.isKeyEncrypted(privateKey)) {
pemContent = certificateCreator.readDecryptedKey(privateKey, passphrase);
if (openSSLService.isKeyEncrypted(privateKey)) {
pemContent = openSSLService.readDecryptedKey(privateKey, passphrase);
} else {
pemContent = Files.readString(privateKey);
}
try (var fis = Files.newInputStream(privateKey)) {
String privateKeyPEM = pemContent
.replaceAll(".*?-----BEGIN PRIVATE KEY-----", "")
.replace("-----END PRIVATE KEY-----", "")
.replaceAll("\\s", "");
byte[] decodedKey = Base64.getDecoder().decode(privateKeyPEM);
return KeyFactory.getInstance("RSA").generatePrivate(new PKCS8EncodedKeySpec(decodedKey));
}
String privateKeyPEM = pemContent
.replaceAll(".*?-----BEGIN PRIVATE KEY-----", "")
.replace("-----END PRIVATE KEY-----", "")
.replaceAll("\\s", "");
byte[] decodedKey = Base64.getDecoder().decode(privateKeyPEM);
return KeyFactory.getInstance("RSA").generatePrivate(new PKCS8EncodedKeySpec(decodedKey));
}
@SneakyThrows
@ -85,4 +143,17 @@ public class KeyStoreManager {
return certFactory.generateCertificates(fis).toArray(Certificate[]::new);
}
}
protected final synchronized CertificateFactory getX509Factory() {
CertificateFactory instance = certFactory.get();
if (instance == null) {
try {
instance = CertificateFactory.getInstance("X.509");
certFactory.set(instance);
} catch (CertificateException e) {
throw new IllegalStateException("X.509 factory missing??", e);
}
}
return instance;
}
}

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@ -1,62 +0,0 @@
package de.mlessmann.certassist.keystore;
import de.mlessmann.certassist.openssl.CertificateUsage;
import java.io.IOException;
import java.nio.file.Files;
import java.nio.file.OpenOption;
import java.nio.file.Path;
import java.nio.file.StandardOpenOption;
import java.security.KeyStore;
import java.security.KeyStoreException;
import java.security.NoSuchAlgorithmException;
import java.security.cert.CertificateException;
import java.security.cert.CertificateFactory;
import java.security.cert.X509Certificate;
import lombok.RequiredArgsConstructor;
import lombok.SneakyThrows;
import lombok.extern.slf4j.Slf4j;
@Slf4j
@RequiredArgsConstructor
public class TruststoreManager {
private static final OpenOption[] CREATE_TRUNCATE = {
StandardOpenOption.CREATE,
StandardOpenOption.TRUNCATE_EXISTING,
};
public KeystoreUsage createTruststore(String truststorePassphrase, CertificateUsage... trustedCertificates) {
try {
Path truststorePath = Files.createTempFile("truststore", ".jks");
truststorePath.toFile().deleteOnExit();
log.debug("Creating truststore at {}", truststorePath);
KeyStore truststore = buildTruststore(trustedCertificates);
try (var outputStream = Files.newOutputStream(truststorePath, CREATE_TRUNCATE)) {
truststore.store(outputStream, truststorePassphrase.toCharArray());
}
return new KeystoreResult(truststorePath);
} catch (IOException | KeyStoreException | CertificateException | NoSuchAlgorithmException e) {
throw new IllegalStateException("Failed to create truststore!", e);
}
}
@SneakyThrows
private static KeyStore buildTruststore(CertificateUsage[] trustedCertificates) {
KeyStore truststore = KeyStore.getInstance(KeyStore.getDefaultType());
truststore.load(null, null);
CertificateFactory certificateFactory = CertificateFactory.getInstance("X.509");
if (trustedCertificates == null || trustedCertificates.length == 0) {
log.warn("No trusted certificates provided, truststore will be empty!");
} else {
for (CertificateUsage trustedCertificate : trustedCertificates) {
try (var inputStream = Files.newInputStream(trustedCertificate.certificatePath())) {
X509Certificate jdkCert = (X509Certificate) certificateFactory.generateCertificate(inputStream);
truststore.setCertificateEntry(trustedCertificate.fingerprint(), jdkCert);
}
}
}
return truststore;
}
}

View file

@ -11,6 +11,7 @@ import lombok.RequiredArgsConstructor;
import lombok.Setter;
@Entity
@Table(uniqueConstraints = { @UniqueConstraint(columnNames = { "fingerprint" }) })
@Data
@RequiredArgsConstructor
public class Certificate {
@ -50,12 +51,13 @@ public class Certificate {
private byte[] cert = new byte[0];
//@Lob - Cannot annotate column: https://github.com/xerial/sqlite-jdbc/issues/135
@Column(nullable = false)
@Column
private byte[] privateKey = new byte[0];
//@Lob - Cannot annotate column: https://github.com/xerial/sqlite-jdbc/issues/135
@Column
private byte[] fullchain;
@Column(nullable = false)
private String fingerprint;
}

View file

@ -16,9 +16,11 @@ public interface CertificateUsage extends AutoCloseable {
/**
* Returns the path to the private key file (on disk, potentially temporary depending on the storage implementation).
* This file should also be encrypted.
* This file should also be encrypted as the file system is considered in-flight.
* @see CertificatePasswordProvider
* @apiNote Return value can be null, when there is no private key (e.g. imported certificates for trust only)
*/
@Nullable
Path certificateKeyPath();
/**

View file

@ -1,7 +1,9 @@
package de.mlessmann.certassist.openssl;
import static de.mlessmann.certassist.Constants.CERTASSIST_TMP_PREFIX;
import static java.util.Objects.requireNonNull;
import static java.util.concurrent.TimeUnit.*;
import static lombok.AccessLevel.PRIVATE;
import static org.slf4j.LoggerFactory.getLogger;
import de.mlessmann.certassist.DeleteRecursiveFileVisitor;
@ -13,14 +15,14 @@ import de.mlessmann.certassist.models.CertificateInfoExtension;
import de.mlessmann.certassist.models.CertificateInfoSubject;
import de.mlessmann.certassist.models.CertificateInfoSubject.CertificateInfoSubjectBuilder;
import de.mlessmann.certassist.service.ExecutableResolver;
import java.io.ByteArrayInputStream;
import java.io.IOException;
import java.nio.charset.StandardCharsets;
import java.nio.file.Files;
import java.nio.file.Path;
import java.nio.file.StandardOpenOption;
import java.util.List;
import java.util.Optional;
import java.util.UUID;
import java.security.cert.X509Certificate;
import java.util.*;
import java.util.concurrent.ExecutionException;
import java.util.concurrent.TimeoutException;
import java.util.concurrent.atomic.AtomicBoolean;
@ -28,11 +30,14 @@ import java.util.concurrent.atomic.AtomicInteger;
import java.util.regex.Matcher;
import java.util.regex.Pattern;
import java.util.stream.Collectors;
import lombok.NoArgsConstructor;
import lombok.RequiredArgsConstructor;
import lombok.SneakyThrows;
import lombok.extern.slf4j.Slf4j;
import org.apache.commons.lang3.StringUtils;
import org.slf4j.Logger;
import org.springframework.lang.NonNull;
import org.springframework.lang.Nullable;
import org.springframework.stereotype.Service;
import org.springframework.util.CollectionUtils;
import org.zeroturnaround.exec.ProcessExecutor;
@ -45,9 +50,9 @@ import org.zeroturnaround.exec.stream.slf4j.Slf4jStream;
@Slf4j
public class OpenSSLService {
private static final Logger openSSLLogger = getLogger("OpenSSL-Logger");
public static final String OPENSSL_CERT_SUBJECT_TEMPLATE =
"/C=ISO-COUNTRY/ST=STATE/L=LOCALITY/O=ORGANIZATION/CN=COMMON-NAME";
private static final Logger openSSLLogger = getLogger("OpenSSL-Logger");
private static final String CSR_EXT_TEMPLATE =
"""
authorityKeyIdentifier=keyid,issuer
@ -105,6 +110,12 @@ public class OpenSSLService {
}
}
private static void requireNotBlank(@Nullable String str, @NonNull String failMessage) {
if (StringUtils.isBlank(str)) {
throw new IllegalArgumentException(failMessage);
}
}
@NonNull
public OpenSSLCertificateResult createCertificate(CertificateInfo request) throws CommandLineOperationException {
Path tmpDir;
@ -126,11 +137,16 @@ public class OpenSSLService {
}
try (var certAuthority = certificateProvider.requestCertificateUsage(request.getTrustingAuthority())) {
Path pKeyPath = requireNonNull(
certAuthority.certificateKeyPath(),
"Cannot sign a certificate with a CA for which the key is not available!"
);
Path signingRequest = createSigningRequest(request, keyFile, tmpDir.resolve("child.csr"), keyPassphrase);
Path signedCert = signCertificate(
request,
certAuthority.certificatePath(),
certAuthority.certificateKeyPath(),
pKeyPath,
passwordProvider.getPasswordFor(certAuthority.fingerprint()),
signingRequest
);
@ -153,11 +169,14 @@ public class OpenSSLService {
}
}
private Path createKeyfile(CertificateInfo request, Path outFile, String filePassword)
@NonNull
private Path createKeyfile(@NonNull CertificateInfo request, @NonNull Path outFile, @NonNull String keyPassphrase)
throws CommandLineOperationException {
requireNotBlank(keyPassphrase, "A passphrase must be provided to generate private keys!");
requireNonNull(outFile, "Output file must be provided to generate keys!");
Path keyFile = outFile.toAbsolutePath();
log.debug("Writing new certificate key to {}", keyFile);
log.debug("Writing new certificate key to {}", keyFile);
StartedProcess keygenProc = null;
try {
keygenProc =
@ -172,7 +191,7 @@ public class OpenSSLService {
OSSL_ARG_KEY_PW,
Integer.toString(request.getRequestedKeyLength())
)
.environment(OSSL_ENV_KEY_PW, filePassword)
.environment(OSSL_ENV_KEY_PW, keyPassphrase)
.redirectOutput(Slf4jStream.of(openSSLLogger).asDebug())
.redirectError(Slf4jStream.of(openSSLLogger).asError())
.start();
@ -185,10 +204,18 @@ public class OpenSSLService {
return keyFile;
}
private Path createCertificate(CertificateInfo request, Path keyFile, Path outFile, String keyPassphrase)
throws CommandLineOperationException {
log.debug("Writing new certificate file {}", outFile);
@NonNull
private Path createCertificate(
@NonNull CertificateInfo request,
@NonNull Path keyFile,
Path outFile,
@NonNull String keyPassphrase
) throws CommandLineOperationException {
requireNonNull(outFile, "Output file must be provided to generate certificates!");
requireNonNull(keyFile, "Private key file must be provided to generate certificates!");
requireNotBlank(keyPassphrase, "Private key passphrase must be provided to generate certificates.");
log.debug("Writing new certificate file {}", outFile);
String certSubject = buildSubjectArg(request);
StartedProcess certGenProc = null;
try {
@ -225,9 +252,17 @@ public class OpenSSLService {
return outFile;
}
private Path createSigningRequest(CertificateInfo request, Path keyFile, Path outFile, String certPassword)
throws CommandLineOperationException {
log.atDebug().log("Writing new certificate signing request file {}", outFile);
@NonNull
private Path createSigningRequest(
@NonNull CertificateInfo request,
@NonNull Path keyFile,
@NonNull Path outFile,
@NonNull String pkeyPassphrase
) throws CommandLineOperationException {
requireNonNull(keyFile, "Private key must be provided to generate CSR!");
requireNonNull(outFile, "Output file must be provided to generate CSR!");
requireNotBlank(pkeyPassphrase, "Passphrase for private key must be provided to create CSR.");
log.debug("Writing new certificate signing request file {}", outFile);
String certSubject = buildSubjectArg(request);
StartedProcess certGenProc = null;
@ -249,7 +284,7 @@ public class OpenSSLService {
"-subj",
certSubject
)
.environment(OSSL_ENV_KEY_PW, certPassword)
.environment(OSSL_ENV_KEY_PW, pkeyPassphrase)
.redirectOutput(Slf4jStream.of(openSSLLogger).asDebug())
.redirectError(Slf4jStream.of(openSSLLogger).asError())
.start();
@ -270,10 +305,10 @@ public class OpenSSLService {
public boolean verifyCertificate(@NonNull Path fullChainFile, @NonNull List<Path> trustedCAs)
throws CommandLineOperationException {
if (CollectionUtils.isEmpty(trustedCAs)) {
throw new IllegalArgumentException(
"At least one trusted CA certificate must be provided to run the verification command."
);
log.warn("No trusted CA provided for verification. Certificate is untrusted.");
return false;
}
requireNonNull(fullChainFile, "Cannot verify certificate without fullChainFile");
Path tmpDir = null;
StartedProcess verifyCommand = null;
@ -335,10 +370,13 @@ public class OpenSSLService {
/**
* Verifies a passphrase against a provided key.
*
* @implNote Due to the implementation of the OpenSSL cli, <em>any password</em> will be valid for unencrypted keys. (Check with {@link #isKeyEncrypted(Path).)
*/
public boolean verifyKeyPassphrase(@NonNull Path keyFile, @NonNull String passphrase)
throws CommandLineOperationException {
requireNonNull(keyFile, "Key file must be provided to check encryption.");
requireNonNull(passphrase, "Must provide a passphrase to check encryption.");
StartedProcess verifyCommand = null;
try {
verifyCommand =
@ -365,16 +403,22 @@ public class OpenSSLService {
}
}
@NonNull
private Path signCertificate(
CertificateInfo request,
Path caCert,
Path caKey,
String caKeyPassphrase,
Path csrFile
@NonNull Path caCert,
@NonNull Path caKey,
@NonNull String caKeyPassphrase,
@NonNull Path csrFile
) throws CommandLineOperationException {
requireNonNull(caCert, "CA certificate must be provided to sign certs!");
requireNonNull(caKey, "CA private key must be provided to sign certs!");
requireNotBlank(caKeyPassphrase, "CA private key passphrase must be provided to sign certs!");
requireNonNull(csrFile, "CSR to be signed must be provided.");
Path outFile = csrFile.resolveSibling(csrFile.getFileName().toString().replace(".csr", ".crt"));
log.debug("Writing new signed certificate file {}", outFile);
Path extFile = csrFile.resolveSibling(csrFile.getFileName().toString().replace(".csr", ".ext"));
log.debug("Writing new signed certificate file {}", outFile);
try {
String extContent = CSR_EXT_TEMPLATE;
@ -394,7 +438,7 @@ public class OpenSSLService {
extContent = extContent.replaceAll("\\[alt_names]\n?", "");
}
log.debug("Writing extension file content: \n {}", extContent);
log.debug("Writing extension file {} with content: \n {}", extFile, extContent);
Files.writeString(
extFile,
extContent,
@ -449,42 +493,64 @@ public class OpenSSLService {
return outFile;
}
public String getCertificateFingerprint(Path certificate) throws CommandLineOperationException {
StartedProcess fingerprintProc = null;
@NonNull
public String getCertificateFingerprint(@NonNull Path certificate) throws CommandLineOperationException {
requireNonNull(certificate, "Certificate must be provided to generate fingerprint.");
try {
fingerprintProc =
new ProcessExecutor()
.command(resolveOpenSSL(), "x509", "-in", certificate.toString(), "-noout", "-fingerprint")
.readOutput(true)
.redirectError(Slf4jStream.of(openSSLLogger).asError())
.start();
return getCertificateFingerprint(Files.readString(certificate));
} catch (IOException e) {
throw new CommandLineOperationException("Certificate content could not be read.", e);
}
}
private String extractFingerprintFromOutput(ProcessResult fingerprintResult) throws CommandLineOperationException {
String output = fingerprintResult.getOutput().getUTF8();
if (fingerprintResult.getExitValue() != 0) {
log.debug("Fingerprint command output:\n{}", output);
throw new CommandLineOperationException(
"Failed to get fingerprint of certificate. Exit code: %d".formatted(fingerprintResult.getExitValue())
);
}
Matcher matcher = FINGERPRINT_EXTRACTOR.matcher(output);
if (!matcher.find()) {
log.debug(output);
throw new CommandLineOperationException(
"Unexpected output of fingerprint command. (See log for more details)"
);
}
String algorithm = matcher.group("algo");
String fingerprint = matcher.group("finger");
if (StringUtils.isBlank(algorithm) || StringUtils.isBlank(fingerprint)) {
throw new CommandLineOperationException(
"Unexpected output of fingerprint command: %s %s".formatted(algorithm, fingerprint)
);
}
return "%s;%s".formatted(algorithm, fingerprint);
}
@NonNull
@SneakyThrows
public String getCertificateFingerPrint(X509Certificate jdkCert) {
String pemContent =
"-----BEGIN CERTIFICATE-----\n%s\n-----END CERTIFICATE-----".formatted(
new String(jdkCert.getEncoded(), StandardCharsets.UTF_8)
);
return getCertificateFingerprint(pemContent);
}
@NonNull
@SneakyThrows
public String getCertificateFingerprint(@NonNull String pemContent) throws CommandLineOperationException {
requireNonNull(pemContent, "Certificate PEM content must be provided to generate fingerprint from string.");
StartedProcess fingerprintProc = null;
try (var input = new ByteArrayInputStream(pemContent.getBytes())) {
fingerprintProc = Commands.fingerprintCommand(resolveOpenSSL()).redirectInput(input).start();
var fingerprintResult = fingerprintProc.getFuture().get(30, SECONDS);
String output = fingerprintResult.getOutput().getUTF8();
if (fingerprintResult.getExitValue() != 0) {
log.debug("Fingerprint command output:\n{}", output);
throw new CommandLineOperationException(
"Failed to get fingerprint of certificate. Exit code: %d".formatted(
fingerprintResult.getExitValue()
)
);
}
Matcher matcher = FINGERPRINT_EXTRACTOR.matcher(output);
if (!matcher.find()) {
log.debug(output);
throw new CommandLineOperationException(
"Unexpected output of fingerprint command. (See log for more details)"
);
}
String algorithm = matcher.group("algo");
String fingerprint = matcher.group("finger");
if (StringUtils.isBlank(algorithm) || StringUtils.isBlank(fingerprint)) {
throw new CommandLineOperationException(
"Unexpected output of fingerprint command: %s %s".formatted(algorithm, fingerprint)
);
}
return "%s;%s".formatted(algorithm, fingerprint);
return extractFingerprintFromOutput(fingerprintResult);
} catch (IOException | ExecutionException | TimeoutException | InterruptedException e) {
throw new RuntimeException(e);
} finally {
@ -492,37 +558,12 @@ public class OpenSSLService {
}
}
public CertificateInfo getCertificateInfo(Path path) throws CommandLineOperationException {
@NonNull
@SneakyThrows
public CertificateInfo getCertificateInfo(String pemContent) {
StartedProcess infoProc = null;
try {
infoProc =
new ProcessExecutor()
.command(
resolveOpenSSL(),
"x509",
"-in",
path.toString(),
"-noout",
"-dateopt",
"iso_8601",
"-fingerprint",
"-subject",
"-issuer",
"-serial",
"-dates",
"-alias",
"-email",
"-purpose",
"-ext",
"subjectAltName",
"-nameopt",
"sep_multiline",
"-nameopt",
"lname"
)
.readOutput(true)
.redirectError(Slf4jStream.of(openSSLLogger).asError())
.start();
try (var input = new ByteArrayInputStream(pemContent.getBytes())) {
infoProc = Commands.infoCommand(resolveOpenSSL()).redirectInput(input).start();
var infoResult = infoProc.getFuture().get(30, SECONDS);
String output = infoResult.getOutput().getUTF8();
if (infoResult.getExitValue() != 0) {
@ -534,9 +575,22 @@ public class OpenSSLService {
return getCertificateInfo(output.lines().toArray(String[]::new));
} catch (IOException | ExecutionException | InterruptedException | TimeoutException e) {
throw new RuntimeException(e);
} finally {
killIfActive(infoProc);
}
}
@NonNull
public CertificateInfo getCertificateInfo(Path path) throws CommandLineOperationException {
requireNonNull(path, "Certificate file must be provided to read the info.");
try {
return getCertificateInfo(Files.readString(path));
} catch (IOException e) {
throw new CommandLineOperationException("Failed to read certificate file.", e);
}
}
@NonNull
private String resolveOpenSSL() throws CommandLineOperationException {
try {
String path = executableResolver.getOpenSSLPath();
@ -621,7 +675,12 @@ public class OpenSSLService {
};
}
public String readDecryptedKey(Path keyFile, String passphrase) throws CommandLineOperationException {
@NonNull
public String readDecryptedKey(@NonNull Path keyFile, @NonNull String passphrase)
throws CommandLineOperationException {
requireNonNull(keyFile, "Key to be decrypted must be provided!");
requireNotBlank(passphrase, "Passphrase for private key must be provided to run decryption.");
StartedProcess keyReadProc = null;
try {
keyReadProc =
@ -646,4 +705,48 @@ public class OpenSSLService {
killIfActive(keyReadProc);
}
}
@NoArgsConstructor(access = PRIVATE)
private static class Commands {
private static ProcessExecutor infoCommand(String openSSL, String... additArgs) {
List<String> command = new ArrayList<>(
List.of(
openSSL,
"x509",
"-noout",
"-dateopt",
"iso_8601",
"-fingerprint",
"-subject",
"-issuer",
"-serial",
"-dates",
"-alias",
"-email",
"-purpose",
"-ext",
"subjectAltName",
"-nameopt",
"sep_multiline",
"-nameopt",
"lname"
)
);
command.addAll(Arrays.asList(additArgs));
return new ProcessExecutor()
.command(command)
.readOutput(true)
.redirectError(Slf4jStream.of(openSSLLogger).asError());
}
private static ProcessExecutor fingerprintCommand(String openSSL, String... additArgs) {
List<String> command = new ArrayList<>(List.of(openSSL, "x509", "-noout", "-fingerprint"));
command.addAll(Arrays.asList(additArgs));
return new ProcessExecutor()
.command(command)
.readOutput(true)
.redirectError(Slf4jStream.of(openSSLLogger).asError());
}
}
}

View file

@ -7,11 +7,20 @@ import de.mlessmann.certassist.repositories.CertificateRepository;
import java.io.IOException;
import java.nio.file.Files;
import java.nio.file.Path;
import java.util.HashMap;
import java.util.List;
import java.util.Map;
import java.util.regex.Matcher;
import java.util.regex.Pattern;
import java.util.stream.StreamSupport;
import lombok.RequiredArgsConstructor;
import lombok.extern.slf4j.Slf4j;
import org.apache.commons.lang3.StringUtils;
import org.springframework.lang.NonNull;
import org.springframework.lang.Nullable;
import org.springframework.stereotype.Service;
@Slf4j
@Service
@RequiredArgsConstructor
public class CertificateCreationService {
@ -19,12 +28,18 @@ public class CertificateCreationService {
private final CertificateRepository certificateRepository;
private final OpenSSLService openSSLService;
private final PassphraseService passphraseService;
private final Pattern CERT_START_PATTERN = Pattern.compile("-+BEGIN CERTIFICATE-+");
private final Pattern CERT_END_PATTERN = Pattern.compile("-+END CERTIFICATE-+");
public Certificate createCertificate(final CertificateInfo certificateInfo) {
final Certificate certificate = createEntityFromRequest(certificateInfo);
try (OpenSSLCertificateResult certificateCreatorResult = openSSLService.createCertificate(certificateInfo);) {
certificate.setPrivateKey(Files.readAllBytes(certificateCreatorResult.certificateKeyPath()));
Path keyPath = certificateCreatorResult.certificateKeyPath();
certificate.setFingerprint(certificateCreatorResult.fingerprint());
if (keyPath != null) {
certificate.setPrivateKey(Files.readAllBytes(keyPath));
}
certificate.setCert(Files.readAllBytes(certificateCreatorResult.certificatePath()));
} catch (CommandLineOperationException | IOException e) {
throw new IllegalStateException("Failed to create certificate!", e);
@ -59,15 +74,23 @@ public class CertificateCreationService {
return certificate;
}
public Certificate importCertificate(Path certificate, Path keyFile, String passphrase) {
@NonNull
public Certificate importCertificate(
@NonNull Path certificate,
@Nullable Path keyFile,
@Nullable String keyPassphrase
) {
try {
String fingerprint = openSSLService.getCertificateFingerprint(certificate);
var generatedRequest = openSSLService.getCertificateInfo(certificate);
Certificate entity = createEntityFromRequest(generatedRequest);
entity.setFingerprint(fingerprint);
entity.setCert(Files.readAllBytes(certificate));
entity.setPrivateKey(Files.readAllBytes(keyFile));
if (StringUtils.isNotBlank(passphrase)) {
passphraseService.storePassphrase("cert:" + fingerprint, passphrase);
if (keyFile != null) {
entity.setPrivateKey(Files.readAllBytes(keyFile));
}
if (StringUtils.isNotBlank(keyPassphrase)) {
passphraseService.storePassphrase("cert:" + fingerprint, keyPassphrase);
}
return certificateRepository.save(entity);
} catch (CommandLineOperationException | IOException e) {
@ -75,6 +98,36 @@ public class CertificateCreationService {
}
}
public List<Certificate> importCertificateTrustBundle(@NonNull Path bundleFile) {
try {
Map<String, Certificate> certsInBundle = new HashMap<>();
String pemContent = Files.readString(bundleFile);
Matcher beginMatcher = CERT_START_PATTERN.matcher(pemContent);
while (beginMatcher.find()) {
int startIdx = beginMatcher.start();
Matcher endMatcher = CERT_END_PATTERN.matcher(pemContent);
if (!endMatcher.find(startIdx)) {
throw new IllegalStateException("Certificate has a startIdx but not an end??");
}
int endIdx = endMatcher.end();
String singleCert = pemContent.substring(startIdx, endIdx);
String fingerprint = openSSLService.getCertificateFingerprint(singleCert);
var generatedRequest = openSSLService.getCertificateInfo(singleCert);
Certificate entity = createEntityFromRequest(generatedRequest);
entity.setFingerprint(fingerprint);
entity.setCert(singleCert.getBytes());
certsInBundle.put(fingerprint, entity);
log.debug("Found certificate in bundle at {} to {}: {}", startIdx, endIdx, fingerprint);
}
var saveResult = certificateRepository.saveAll(certsInBundle.values());
return StreamSupport.stream(saveResult.spliterator(), false).toList();
} catch (CommandLineOperationException | IOException e) {
throw new RuntimeException("Unable to import certificate", e);
}
}
private CertificateType mapCertificateRequestType(CertificateInfo.RequestType requestType) {
return switch (requestType) {
case ROOT_AUTHORITY -> CertificateType.ROOT_CA;

View file

@ -1,5 +1,7 @@
package de.mlessmann.certassist.service;
import static java.util.Objects.requireNonNull;
import de.mlessmann.certassist.Constants;
import de.mlessmann.certassist.DeleteRecursiveFileVisitor;
import de.mlessmann.certassist.models.Certificate;
@ -29,7 +31,14 @@ public class CertificateProviderImpl implements CertificateProvider {
@Override
public CertificateUsage requestCertificateUsage(String fingerprint) {
Certificate certFromDB = certificateRepository.findByFingerprintIs(fingerprint);
requireNonNull(fingerprint, "Fingerprint must be provided.");
Certificate certFromDB;
try {
certFromDB = certificateRepository.findByFingerprintIs(fingerprint);
} catch (RuntimeException e) {
log.error("Failed to retrieve certificate from database by fingerprint: {}", fingerprint);
throw e;
}
if (certFromDB == null) {
throw new IllegalArgumentException("Unknown fingerprint");
}

View file

@ -2,11 +2,18 @@ package de.mlessmann.certassist;
import static org.assertj.core.api.Assertions.assertThat;
import de.mlessmann.certassist.keystore.KeyStoreManager;
import de.mlessmann.certassist.models.Certificate;
import de.mlessmann.certassist.models.CertificateInfo;
import de.mlessmann.certassist.models.CertificateInfoExtension;
import de.mlessmann.certassist.models.CertificateInfoSubject;
import de.mlessmann.certassist.openssl.CertificateProvider;
import de.mlessmann.certassist.openssl.CertificateUsage;
import de.mlessmann.certassist.repositories.CertificateRepository;
import de.mlessmann.certassist.service.CertificateCreationService;
import java.nio.file.Path;
import java.util.List;
import org.junit.jupiter.api.BeforeEach;
import org.junit.jupiter.api.Test;
import org.springframework.beans.factory.annotation.Autowired;
import org.springframework.boot.test.context.SpringBootTest;
@ -14,8 +21,24 @@ import org.springframework.boot.test.context.SpringBootTest;
@SpringBootTest
public class CertificateServiceTest {
public static final Path LETSENCRYPT_CERT_PATH = Path.of("src/test/resources/letsencrypt");
@Autowired
private CertificateCreationService certificateService;
CertificateRepository certificateRepository;
@Autowired
CertificateCreationService certificateService;
@Autowired
KeyStoreManager keyStoreManager;
@Autowired
CertificateProvider certificateProvider;
@BeforeEach
void setUp() {
certificateRepository.deleteAll();
}
@Test
void testCanCreateCertificate() {
@ -49,4 +72,30 @@ public class CertificateServiceTest {
assertThat(importedCert).isNotNull();
assertThat(importedCert.getId()).isGreaterThan("0");
}
@Test
void testCanImportTrustCertificate() {
Path cert = LETSENCRYPT_CERT_PATH.resolve("2024-11-isrgrootx1.pem");
var importedCert = certificateService.importCertificate(cert, null, null);
assertThat(importedCert).isNotNull();
assertThat(importedCert.getId()).isGreaterThan("0");
}
@Test
void testCanImportTrustBundles() throws Exception {
Path cert = LETSENCRYPT_CERT_PATH.resolve("2024-11-letsencrypt.bundle.pem");
List<Certificate> importedCerts = certificateService.importCertificateTrustBundle(cert);
List<CertificateUsage> tmpUsableCerts = importedCerts
.stream()
.map(Certificate::getFingerprint)
.map(certificateProvider::requestCertificateUsage)
.toList();
try (var store = keyStoreManager.createTruststore("changeit", tmpUsableCerts)) {
assertThat(store).isNotNull();
assertThat(store.truststorePath()).isRegularFile();
} finally {
tmpUsableCerts.forEach(CertificateUsage::close);
}
}
}

View file

@ -3,7 +3,6 @@ package de.mlessmann.certassist;
import static org.assertj.core.api.Assertions.assertThat;
import de.mlessmann.certassist.keystore.KeyStoreManager;
import de.mlessmann.certassist.keystore.TruststoreManager;
import de.mlessmann.certassist.openssl.CertificateProvider;
import de.mlessmann.certassist.openssl.CertificateUsage;
import de.mlessmann.certassist.openssl.InMemoryCertificatePasswordProvider;
@ -53,13 +52,12 @@ public class TestKeystoreCreation {
var certificateProvider = Mockito.mock(CertificateProvider.class);
var opensslCertCreator = new OpenSSLService(new ExecutableResolver(), passwordProvider, certificateProvider);
var truststoreManager = new TruststoreManager();
var keyStoreManager = new KeyStoreManager(opensslCertCreator, passwordProvider);
AtomicBoolean serverAccepted = new AtomicBoolean(false);
AtomicBoolean clientAccepted = new AtomicBoolean(false);
try (
var tmpTruststore = truststoreManager.createTruststore(STORE_PASSPHRASE, dummyCert);
var tmpTruststore = keyStoreManager.createTruststore(STORE_PASSPHRASE, dummyCert);
var tmpKeyStore = keyStoreManager.createKeyStore(STORE_PASSPHRASE, dummyCert)
) {
KeyManagerFactory keyManagerFactory = KeyManagerFactory.getInstance(
@ -69,7 +67,6 @@ public class TestKeystoreCreation {
SSLContext tlsSrvContext = SSLContext.getInstance("TLS");
tlsSrvContext.init(keyManagerFactory.getKeyManagers(), null, TEST_RANDOM);
int serverPort = 1024 + TEST_RANDOM.nextInt(22_000);
ServerSocket serverSocket = tlsSrvContext.getServerSocketFactory().createServerSocket(0);
var serverThread = Thread.startVirtualThread(() -> {

View file

@ -53,6 +53,7 @@ class CertificateRepositoryTest {
@Transactional
void findCertificateWithExtension() {
final Certificate certificate = getCertificate();
certificate.setFingerprint("test-fingerprint");
CertificateExtension extension = new CertificateExtension();
extension.setValue("test-ext-value");
certificate.setCertificateExtension(List.of(extension));

View file

@ -0,0 +1,14 @@
-----BEGIN CERTIFICATE-----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-----END CERTIFICATE-----

View file

@ -0,0 +1,31 @@
-----BEGIN CERTIFICATE-----
MIIFazCCA1OgAwIBAgIRAIIQz7DSQONZRGPgu2OCiwAwDQYJKoZIhvcNAQELBQAw
TzELMAkGA1UEBhMCVVMxKTAnBgNVBAoTIEludGVybmV0IFNlY3VyaXR5IFJlc2Vh
cmNoIEdyb3VwMRUwEwYDVQQDEwxJU1JHIFJvb3QgWDEwHhcNMTUwNjA0MTEwNDM4
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emyPxgcYxn/eR44/KJ4EBs+lVDR3veyJm+kXQ99b21/+jh5Xos1AnX5iItreGCc=
-----END CERTIFICATE-----

View file

@ -0,0 +1,45 @@
-----BEGIN CERTIFICATE-----
MIICGzCCAaGgAwIBAgIQQdKd0XLq7qeAwSxs6S+HUjAKBggqhkjOPQQDAzBPMQsw
CQYDVQQGEwJVUzEpMCcGA1UEChMgSW50ZXJuZXQgU2VjdXJpdHkgUmVzZWFyY2gg
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/q4AaOeMSQ+2b1tbFfLn
-----END CERTIFICATE-----
-----BEGIN CERTIFICATE-----
MIIFazCCA1OgAwIBAgIRAIIQz7DSQONZRGPgu2OCiwAwDQYJKoZIhvcNAQELBQAw
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-----END CERTIFICATE-----