public async Task GetTimestamp_WhenSignatureHashAlgorithmIsSha1_Throws()
{
var testServer = await _testFixture.GetSigningTestServerAsync();
var certificateAuthority = await _testFixture.GetDefaultTrustedCertificateAuthorityAsync();
var options = new TimestampServiceOptions()
{
SignatureHashAlgorithm = new Oid(Oids.Sha1)
};
var timestampService = TimestampService.Create(certificateAuthority, options);
VerifyTimestampData(
testServer,
timestampService,
(timestampProvider, request) =>
{
var exception = Assert.Throws <TimestampException>(
() => timestampProvider.GetTimestamp(request, NullLogger.Instance, CancellationToken.None));
Assert.Equal(
"The timestamp certificate has an unsupported signature algorithm.",
exception.Message);
});
}
public async Task GetTimestamp_WithFailureReponse_Throws()
{
var testServer = await _testFixture.GetSigningTestServerAsync();
var certificateAuthority = await _testFixture.GetDefaultTrustedCertificateAuthorityAsync();
var options = new TimestampServiceOptions()
{
ReturnFailure = true
};
var timestampService = TimestampService.Create(certificateAuthority, options);
VerifyTimestampData(
testServer,
timestampService,
(timestampProvider, request) =>
{
var exception = Assert.Throws <CryptographicException>(
() => timestampProvider.GetTimestamp(request, NullLogger.Instance, CancellationToken.None));
Assert.StartsWith(
"The timestamp signature and/or certificate could not be verified or is malformed.",
exception.Message);
});
}
public async Task GetTimestampAsync_WhenCertificateSignatureAlgorithmIsSha1_ThrowsAsync()
{
var testServer = await _testFixture.GetSigningTestServerAsync();
var certificateAuthority = await _testFixture.GetDefaultTrustedCertificateAuthorityAsync();
var timestampServiceOptions = new TimestampServiceOptions()
{
SignatureHashAlgorithm = new Oid(Oids.Sha1)
};
var issueCertificateOptions = IssueCertificateOptions.CreateDefaultForTimestampService();
issueCertificateOptions.SignatureAlgorithmName = "SHA1WITHRSA";
var timestampService = TimestampService.Create(certificateAuthority, timestampServiceOptions, issueCertificateOptions);
VerifyTimestampData(
testServer,
timestampService,
async(timestampProvider, request) =>
{
var exception = await Assert.ThrowsAsync <TimestampException>(
() => timestampProvider.GetTimestampAsync(request, NullLogger.Instance, CancellationToken.None));
Assert.Equal(
"The timestamp certificate has an unsupported signature algorithm (SHA1RSA). The following algorithms are supported: SHA256RSA, SHA384RSA, SHA512RSA.",
exception.Message);
});
}
public async Task GetTimestampAsync_TimestampGeneralizedTimeOutsideCertificateValidityPeriod_FailAsync()
{
// Arrange
var testServer = await _testFixture.GetSigningTestServerAsync();
var certificateAuthority = await _testFixture.GetDefaultTrustedCertificateAuthorityAsync();
var options = new TimestampServiceOptions()
{
IssuedCertificateNotBefore = DateTimeOffset.UtcNow.AddHours(-1),
IssuedCertificateNotAfter = DateTimeOffset.UtcNow.AddHours(1),
GeneralizedTime = DateTimeOffset.UtcNow.AddHours(3)
};
var timestampService = TimestampService.Create(certificateAuthority, options);
VerifyTimestampData(
testServer,
timestampService,
async(timestampProvider, request) =>
{
var exception = await Assert.ThrowsAsync <TimestampException>(
() => timestampProvider.GetTimestampAsync(request, NullLogger.Instance, CancellationToken.None));
Assert.Equal(NuGetLogCode.NU3036, exception.Code);
Assert.Contains(
"The timestamp's generalized time is outside the timestamping certificate's validity period.",
exception.Message);
});
}
public async Task GetTimestampCertificateChain_WithNoSigningCertificateUsage_Throws()
{
ISigningTestServer testServer = await _testFixture.GetSigningTestServerAsync();
CertificateAuthority rootCa = await _testFixture.GetDefaultTrustedCertificateAuthorityAsync();
var options = new TimestampServiceOptions()
{
SigningCertificateUsage = SigningCertificateUsage.None
};
TimestampService timestampService = TimestampService.Create(rootCa, options);
using (testServer.RegisterResponder(timestampService))
{
var nupkg = new SimpleTestPackageContext();
using (var certificate = new X509Certificate2(_testFixture.TrustedTestCertificate.Source.Cert))
using (TestDirectory directory = TestDirectory.Create())
{
string signedPackagePath = await SignedArchiveTestUtility.AuthorSignPackageAsync(
certificate,
nupkg,
directory,
timestampService.Url);
// Act
CommandRunnerResult result = RunVerifyCommand(signedPackagePath);
// Assert
result.Success.Should().BeFalse(because: result.AllOutput);
result.AllOutput.Should().Contain("Either the signing-certificate or signing-certificate-v2 attribute must be present.");
result.AllOutput.Should().NotContain(_successfullyVerified);
}
}
}
public async Task SignCommand_SignPackageWithUnsuportedTimestampHashAlgorithm_ShouldNotModifyPackageAsync()
{
var testServer = await _testFixture.GetSigningTestServerAsync();
var certificateAuthority = await _testFixture.GetDefaultTrustedCertificateAuthorityAsync();
var options = new TimestampServiceOptions()
{
SignatureHashAlgorithm = new Oid(Oids.Sha1)
};
var timestampService = TimestampService.Create(certificateAuthority, options);
using (testServer.RegisterResponder(timestampService))
using (var directory = TestDirectory.Create())
{
var packageContext = new SimpleTestPackageContext();
var packageFile = packageContext.CreateAsFile(directory, fileName: Guid.NewGuid().ToString());
var originalFile = File.ReadAllBytes(packageFile.FullName);
using (var certificate = _testFixture.UntrustedSelfIssuedCertificateInCertificateStore)
{
var result = CommandRunner.Run(
_nugetExePath,
directory,
$"sign {packageFile.FullName} -CertificateFingerprint {certificate.Thumbprint} -Timestamper {timestampService.Url}",
waitForExit: true);
Assert.False(result.Success);
Assert.Contains("The timestamp certificate has an unsupported signature algorithm.", result.AllOutput);
var resultingFile = File.ReadAllBytes(packageFile.FullName);
Assert.Equal(resultingFile, originalFile);
}
}
}
public async Task VerifySignaturesAsync_ExpiredCertificateAndTimestampWithTooLargeRange_FailsAsync()
{
ISigningTestServer testServer = await _testFixture.GetSigningTestServerAsync();
CertificateAuthority ca = await _testFixture.GetDefaultTrustedCertificateAuthorityAsync();
var accuracy = new BcAccuracy(seconds: new DerInteger(30), millis: null, micros: null);
var serviceOptions = new TimestampServiceOptions()
{
Accuracy = accuracy
};
TimestampService timestampService = TimestampService.Create(ca, serviceOptions);
AsymmetricCipherKeyPair keyPair = SigningTestUtility.GenerateKeyPair(publicKeyLength: 2048);
DateTimeOffset now = DateTimeOffset.UtcNow;
var issueOptions = new IssueCertificateOptions()
{
KeyPair = keyPair,
NotAfter = now.AddSeconds(10),
NotBefore = now.AddSeconds(-2),
SubjectName = new X509Name("CN=NuGet Test Expired Certificate")
};
BcX509Certificate bcCertificate = ca.IssueCertificate(issueOptions);
using (testServer.RegisterResponder(timestampService))
using (TestDirectory directory = TestDirectory.Create())
using (X509Certificate2 certificate = CertificateUtilities.GetCertificateWithPrivateKey(bcCertificate, keyPair))
{
var packageContext = new SimpleTestPackageContext();
string signedPackagePath = await SignedArchiveTestUtility.AuthorSignPackageAsync(
certificate,
packageContext,
directory,
timestampService.Url);
await SignatureTestUtility.WaitForCertificateExpirationAsync(certificate);
var verifier = new PackageSignatureVerifier(_trustProviders);
using (var packageReader = new PackageArchiveReader(signedPackagePath))
{
VerifySignaturesResult results = await verifier.VerifySignaturesAsync(packageReader, _verifyCommandSettings, CancellationToken.None);
PackageVerificationResult result = results.Results.Single();
Assert.False(results.IsValid);
Assert.Equal(SignatureVerificationStatus.Disallowed, result.Trust);
Assert.Equal(1, result.Issues.Count(issue => issue.Level == LogLevel.Error));
Assert.Equal(0, result.Issues.Count(issue => issue.Level == LogLevel.Warning));
Assert.Contains(result.Issues, issue =>
issue.Code == NuGetLogCode.NU3037 &&
issue.Level == LogLevel.Error &&
issue.Message.Contains("validity period has expired."));
}
}
}
public async Task <CustomTimestampService> CreateCustomTimestampServiceAsync(TimestampServiceOptions options)
{
var testServer = await _testServer.Value;
var rootCa = await _rootCertificateAuthority.Value;
var timestampService = TimestampService.Create(rootCa, options);
var responders = testServer.RegisterDefaultResponders(timestampService);
return(new CustomTimestampService(
timestampService.Url,
responders));
}
public async Task GetTimestampCertificateChain_WithMismatchedEssCertIdCertificateHash_ReturnsChain(
SigningCertificateUsage signingCertificateUsage)
{
ISigningTestServer testServer = await _fixture.GetSigningTestServerAsync();
CertificateAuthority rootCa = await _fixture.GetDefaultTrustedCertificateAuthorityAsync();
var options = new TimestampServiceOptions()
{
SigningCertificateUsage = signingCertificateUsage,
SigningCertificateV1Hash = new byte[SHA1HashLength]
};
TimestampService timestampService = TimestampService.Create(rootCa, options);
using (testServer.RegisterResponder(timestampService))
{
var nupkg = new SimpleTestPackageContext();
using (var certificate = new X509Certificate2(_fixture.TrustedTestCertificate.Source.Cert))
using (var directory = TestDirectory.Create())
{
var signedPackagePath = await SignedArchiveTestUtility.AuthorSignPackageAsync(
certificate,
nupkg,
directory,
timestampService.Url);
using (FileStream stream = File.OpenRead(signedPackagePath))
using (var reader = new PackageArchiveReader(stream))
{
PrimarySignature signature = await reader.GetPrimarySignatureAsync(CancellationToken.None);
using (IX509CertificateChain actualChain = SignatureUtility.GetTimestampCertificateChain(signature))
{
Assert.NotEmpty(actualChain);
IReadOnlyList <Org.BouncyCastle.X509.X509Certificate> expectedChain = GetExpectedCertificateChain(timestampService);
Assert.Equal(expectedChain.Count, actualChain.Count);
for (var i = 0; i < expectedChain.Count; ++i)
{
Org.BouncyCastle.X509.X509Certificate expectedCertificate = expectedChain[i];
X509Certificate2 actualCertificate = actualChain[i];
Assert.True(
expectedCertificate.GetEncoded().SequenceEqual(actualCertificate.RawData),
$"The certificate at index {i} in the chain is unexpected.");
}
}
}
}
}
}
public async Task DotnetSign_SignPackageWithUnsuportedTimestampHashAlgorithm_FailsAsync()
{
// Arrange
using (SimpleTestPathContext pathContext = _msbuildFixture.CreateSimpleTestPathContext())
{
await SimpleTestPackageUtility.CreatePackagesAsync(
pathContext.PackageSource,
new SimpleTestPackageContext("PackageA", "1.0.0"));
string packageFilePath = Path.Combine(pathContext.PackageSource, "PackageA.1.0.0.nupkg");
byte[] originalFile = File.ReadAllBytes(packageFilePath);
ISigningTestServer testServer = await _signFixture.GetSigningTestServerAsync();
CertificateAuthority certificateAuthority = await _signFixture.GetDefaultTrustedCertificateAuthorityAsync();
var options = new TimestampServiceOptions()
{
SignatureHashAlgorithm = new Oid(Oids.Sha1)
};
TimestampService timestampService = TimestampService.Create(certificateAuthority, options);
IX509StoreCertificate storeCertificate = _signFixture.UntrustedSelfIssuedCertificateInCertificateStore;
using (testServer.RegisterResponder(timestampService))
{
// Act
CommandRunnerResult result = _msbuildFixture.RunDotnet(
pathContext.PackageSource,
$"nuget sign {packageFilePath} " +
$"--certificate-fingerprint {storeCertificate.Certificate.Thumbprint} " +
$"--timestamper {timestampService.Url}",
ignoreExitCode: true);
// Assert
result.Success.Should().BeFalse(because: result.AllOutput);
result.AllOutput.Should().Contain(_timestampUnsupportedDigestAlgorithmCode);
Assert.Contains("The timestamp signature has an unsupported digest algorithm (SHA1). The following algorithms are supported: SHA256, SHA384, SHA512.", result.AllOutput);
byte[] resultingFile = File.ReadAllBytes(packageFilePath);
Assert.Equal(resultingFile, originalFile);
}
}
}
public async Task GetTimestampCertificateChain_WithShortEssCertIdCertificateHash_Throws(
SigningCertificateUsage signingCertificateUsage)
{
ISigningTestServer testServer = await _fixture.GetSigningTestServerAsync();
CertificateAuthority rootCa = await _fixture.GetDefaultTrustedCertificateAuthorityAsync();
var options = new TimestampServiceOptions()
{
SigningCertificateUsage = signingCertificateUsage,
SigningCertificateV1Hash = new byte[SHA1HashLength - 1]
};
TimestampService timestampService = TimestampService.Create(rootCa, options);
using (testServer.RegisterResponder(timestampService))
{
var nupkg = new SimpleTestPackageContext();
using (var certificate = new X509Certificate2(_fixture.TrustedTestCertificate.Source.Cert))
using (var directory = TestDirectory.Create())
{
var signedPackagePath = await SignedArchiveTestUtility.AuthorSignPackageAsync(
certificate,
nupkg,
directory,
timestampService.Url);
using (FileStream stream = File.OpenRead(signedPackagePath))
using (var reader = new PackageArchiveReader(stream))
{
PrimarySignature signature = await reader.GetPrimarySignatureAsync(CancellationToken.None);
var exception = Assert.Throws <SignatureException>(
() => SignatureUtility.GetTimestampCertificateChain(signature));
Assert.Equal(
"A certificate referenced by the signing-certificate attribute could not be found.",
exception.Message);
}
}
}
}
public async Task GetTimestamp_WhenSigningCertificateNotReturned_Throws()
{
var testServer = await _testFixture.GetSigningTestServerAsync();
var certificateAuthority = await _testFixture.GetDefaultTrustedCertificateAuthorityAsync();
var options = new TimestampServiceOptions()
{
ReturnSigningCertificate = false
};
var timestampService = TimestampService.Create(certificateAuthority, options);
VerifyTimestampData(
testServer,
timestampService,
(timestampProvider, request) =>
{
var exception = Assert.Throws <CryptographicException>(
() => timestampProvider.GetTimestamp(request, NullLogger.Instance, CancellationToken.None));
Assert.StartsWith("Cannot find object or property.", exception.Message);
});
}
public async Task GetTimestampCertificateChain_WithMismatchedEssCertIdCertificateHash_ReturnsChain(
SigningCertificateUsage signingCertificateUsage)
{
ISigningTestServer testServer = await _testFixture.GetSigningTestServerAsync();
CertificateAuthority rootCa = await _testFixture.GetDefaultTrustedCertificateAuthorityAsync();
var options = new TimestampServiceOptions()
{
SigningCertificateUsage = signingCertificateUsage,
SigningCertificateV1Hash = new byte[SHA1HashLength]
};
TimestampService timestampService = TimestampService.Create(rootCa, options);
using (testServer.RegisterResponder(timestampService))
{
var nupkg = new SimpleTestPackageContext();
using (var certificate = new X509Certificate2(_testFixture.TrustedTestCertificate.Source.Cert))
using (TestDirectory directory = TestDirectory.Create())
{
string signedPackagePath = await SignedArchiveTestUtility.AuthorSignPackageAsync(
certificate,
nupkg,
directory,
timestampService.Url);
// Act
CommandRunnerResult result = RunVerifyCommand(signedPackagePath);
// Assert
result.Success.Should().BeTrue(because: result.AllOutput);
result.AllOutput.Should().Contain(_successfullyVerified);
Regex.Matches(result.AllOutput, _noTimestamperWarning).Count.Should().Be(0);
}
}
}
public async Task VerifySignaturesAsync_ExpiredCertificateAndTimestampWithTooLargeRange_Fails()
{
var testServer = await _testFixture.GetSigningTestServerAsync();
var ca = await _testFixture.GetDefaultTrustedCertificateAuthorityAsync();
var accuracy = new BcAccuracy(seconds: new DerInteger(30), millis: null, micros: null);
var serviceOptions = new TimestampServiceOptions()
{
Accuracy = accuracy
};
var timestampService = TimestampService.Create(ca, serviceOptions);
var keyPair = SigningTestUtility.GenerateKeyPair(publicKeyLength: 2048);
var now = DateTimeOffset.UtcNow;
var issueOptions = new IssueCertificateOptions()
{
KeyPair = keyPair,
NotAfter = now.AddSeconds(10),
NotBefore = now.AddSeconds(-2),
SubjectName = new X509Name("CN=NuGet Test Expired Certificate")
};
var bcCertificate = ca.IssueCertificate(issueOptions);
using (testServer.RegisterResponder(timestampService))
using (var certificate = new X509Certificate2(bcCertificate.GetEncoded()))
using (var directory = TestDirectory.Create())
{
certificate.PrivateKey = DotNetUtilities.ToRSA(keyPair.Private as RsaPrivateCrtKeyParameters);
var packageContext = new SimpleTestPackageContext();
var signedPackagePath = await SignedArchiveTestUtility.AuthorSignPackageAsync(
certificate,
packageContext,
directory,
timestampService.Url);
var waitDuration = (issueOptions.NotAfter - DateTimeOffset.UtcNow).Add(TimeSpan.FromSeconds(1));
// Wait for the certificate to expire. Trust of the signature will require a valid timestamp.
if (waitDuration > TimeSpan.Zero)
{
await Task.Delay(waitDuration);
}
Assert.True(DateTime.UtcNow > issueOptions.NotAfter);
var verifier = new PackageSignatureVerifier(_trustProviders);
using (var packageReader = new PackageArchiveReader(signedPackagePath))
{
var results = await verifier.VerifySignaturesAsync(packageReader, _verifyCommandSettings, CancellationToken.None);
var result = results.Results.Single();
Assert.False(results.Valid);
Assert.Equal(SignatureVerificationStatus.Illegal, result.Trust);
Assert.Equal(1, result.Issues.Count(issue => issue.Level == LogLevel.Error));
Assert.Equal(0, result.Issues.Count(issue => issue.Level == LogLevel.Warning));
Assert.Contains(result.Issues, issue =>
issue.Code == NuGetLogCode.NU3011 &&
issue.Level == LogLevel.Error &&
issue.Message.Contains("validity period has expired."));
}
}
}
