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feat: Verify key is unencrypted using two random passphrases

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Magnus Leßmann (@MarkL4YG) 2024-11-23 12:36:38 +01:00
parent 334d97c883
commit 5da1e5894d
Signed by: Mark.TwoFive
GPG key ID: 5B5EBCBE331F1E6F
1 changed files with 18 additions and 11 deletions
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29
src/main/java/de/mlessmann/certassist/openssl/OpenSSLCertificateCreator.java
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@ -15,6 +15,7 @@ import java.nio.file.Path;
import java.nio.file.StandardOpenOption;
import java.util.List;
import java.util.Optional;
import java.util.UUID;
import java.util.concurrent.ExecutionException;
import java.util.concurrent.atomic.AtomicBoolean;
import java.util.concurrent.atomic.AtomicInteger;
@ -25,7 +26,6 @@ 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;
import org.springframework.util.CollectionUtils;
import org.zeroturnaround.exec.ProcessExecutor;
@ -135,6 +135,7 @@ public class OpenSSLCertificateCreator {
"genrsa",
"-out",
keyFile.toString(),
"-aes256",
"-passout",
"env:KEY_PASS",
Integer.toString(request.getRequestedKeyLength())
@ -282,20 +283,28 @@ public class OpenSSLCertificateCreator {
}
}
/**
* Checks whether the provided key file is encrypted using a passphrase
*/
public boolean isKeyEncrypted(@NonNull Path keyFile) throws InterruptedException, CommandLineOperationException {
// If any random passphrase works, the key is not encrypted.
return !verifyKeyPassphrase(keyFile, null);
// If the key is not encrypted, any passphrase will work -> so generate a random one to check.
String passphrase = UUID.randomUUID().toString();
boolean firstPass = verifyKeyPassphrase(keyFile, passphrase);
if (firstPass) {
// Try with another random passphrase in case we randomly got lucky guessing the passphrase the first time.
passphrase = UUID.randomUUID().toString();
return !verifyKeyPassphrase(keyFile, passphrase);
}
return true;
}
/**
* Verifies a passphrase against a provided key.
* @implNote Due to the implementation of the OpenSSL cli, any password will be valid for unencrypted keys. (Check with {@link #isKeyEncrypted(Path) or by passing {@code null} as the passphrase.)
* @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, @Nullable String passphrase)
public boolean verifyKeyPassphrase(@NonNull Path keyFile, @NonNull String passphrase)
throws CommandLineOperationException, InterruptedException {
// Run OpenSSL command: openssl rsa -check -in <keyFile> -passin pass:<randomKey> -noout and check exit code
try {
String keyPass = passphrase != null ? passphrase : passwordProvider.generateNewPassword();
StartedProcess verifyCommand = new ProcessExecutor()
.command(
resolveOpenSSL(),
@ -304,16 +313,14 @@ public class OpenSSLCertificateCreator {
"-in",
keyFile.toString(),
"-passin",
"pass:" + keyPass,
"pass:" + passphrase,
"-noout"
)
.redirectOutput(Slf4jStream.ofCaller().asError())
.redirectError(Slf4jStream.ofCaller().asError())
.start();
var verifyResult = verifyCommand.getFuture().get();
boolean commandSuccess = verifyResult.getExitValue() == 0;
log.trace("Key check {} with passphrase provided={}", commandSuccess, passphrase != null);
return commandSuccess;
return verifyResult.getExitValue() == 0;
} catch (IOException | InterruptedException | ExecutionException e) {
throw new CommandLineOperationException("Failed to verify key encryption", e);
}