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[PM-19601] Introduce options for adding certificates to trust without root (#5609)

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* Introduce options for adding certificates to the X509ChainPolicy.CustomTrustStore

Co-authored-by: tangowithfoxtrot <tangowithfoxtrot@users.noreply.github.com>

* Add comments

* Fix places I am still calling it TLS options

* Format

* Format from root

* Add more tests

* Add HTTP Tests

* Format

* Switch to empty builder

* Remove unneeded helper

* Configure logging only once

---------

Co-authored-by: tangowithfoxtrot <tangowithfoxtrot@users.noreply.github.com>
This commit is contained in:
Justin Baur
2025-04-07 14:10:36 -04:00
committed by GitHub
parent 1cf9ff34c1
commit a8403f3dc2
9 changed files with 610 additions and 26 deletions
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61
test/Core.IntegrationTest/MailKitSmtpMailDeliveryServiceTests.cs
View File

@ -1,11 +1,13 @@
using System.Security.Cryptography;
using System.Security.Cryptography.X509Certificates;
using Bit.Core.Models.Mail;
using Bit.Core.Platform.X509ChainCustomization;
using Bit.Core.Services;
using Bit.Core.Settings;
using MailKit.Security;
using Microsoft.Extensions.Logging;
using Microsoft.Extensions.Logging.Abstractions;
using Microsoft.Extensions.Options;
using Rnwood.SmtpServer;
using Rnwood.SmtpServer.Extensions.Auth;
using Xunit.Abstractions;
@ -14,6 +16,7 @@ namespace Bit.Core.IntegrationTest;
public class MailKitSmtpMailDeliveryServiceTests
{
private static int _loggingConfigured;
private readonly X509Certificate2 _selfSignedCert;
public MailKitSmtpMailDeliveryServiceTests(ITestOutputHelper testOutputHelper)
@ -30,13 +33,14 @@ public class MailKitSmtpMailDeliveryServiceTests
return certRequest.CreateSelfSigned(DateTimeOffset.UtcNow, DateTimeOffset.UtcNow.AddYears(1));
}
private static async Task SaveCertAsync(string filePath, X509Certificate2 certificate)
{
await File.WriteAllBytesAsync(filePath, certificate.Export(X509ContentType.Cert));
}
private static void ConfigureSmtpServerLogging(ITestOutputHelper testOutputHelper)
{
// The logging in SmtpServer is configured statically so if we add it for each test it duplicates
// but we cant add the logger statically either because we need ITestOutputHelper
if (Interlocked.CompareExchange(ref _loggingConfigured, 1, 0) == 0)
{
return;
}
// Unfortunately this package doesn't public expose its logging infrastructure
// so we use private reflection to try and access it.
try
@ -100,7 +104,8 @@ public class MailKitSmtpMailDeliveryServiceTests
var mailKitDeliveryService = new MailKitSmtpMailDeliveryService(
globalSettings,
NullLogger<MailKitSmtpMailDeliveryService>.Instance
NullLogger<MailKitSmtpMailDeliveryService>.Instance,
Options.Create(new X509ChainOptions())
);
await Assert.ThrowsAsync<SslHandshakeException>(
@ -113,7 +118,7 @@ public class MailKitSmtpMailDeliveryServiceTests
);
}
[Fact(Skip = "Upcoming feature")]
[Fact]
public async Task SendEmailAsync_SmtpServerUsingSelfSignedCert_CertInCustomLocation_Works()
{
// If an SMTP server is using a self signed cert we will in the future
@ -130,12 +135,18 @@ public class MailKitSmtpMailDeliveryServiceTests
gs.Mail.Smtp.Ssl = true;
});
// TODO: Setup custom location and save self signed cert there.
// await SaveCertAsync("./my-location", _selfSignedCert);
var x509ChainOptions = new X509ChainOptions
{
AdditionalCustomTrustCertificates =
[
_selfSignedCert,
],
};
var mailKitDeliveryService = new MailKitSmtpMailDeliveryService(
globalSettings,
NullLogger<MailKitSmtpMailDeliveryService>.Instance
NullLogger<MailKitSmtpMailDeliveryService>.Instance,
Options.Create(x509ChainOptions)
);
var tcs = new TaskCompletionSource();
@ -162,7 +173,7 @@ public class MailKitSmtpMailDeliveryServiceTests
await tcs.Task;
}
[Fact(Skip = "Upcoming feature")]
[Fact]
public async Task SendEmailAsync_SmtpServerUsingSelfSignedCert_CertInCustomLocation_WithUnrelatedCerts_Works()
{
// If an SMTP server is using a self signed cert we will in the future
@ -179,15 +190,19 @@ public class MailKitSmtpMailDeliveryServiceTests
gs.Mail.Smtp.Ssl = true;
});
// TODO: Setup custom location and save self signed cert there
// along with another self signed cert that is not related to
// the SMTP server.
// await SaveCertAsync("./my-location", _selfSignedCert);
// await SaveCertAsync("./my-location", CreateSelfSignedCert("example.com"));
var x509ChainOptions = new X509ChainOptions
{
AdditionalCustomTrustCertificates =
[
_selfSignedCert,
CreateSelfSignedCert("example.com"),
],
};
var mailKitDeliveryService = new MailKitSmtpMailDeliveryService(
globalSettings,
NullLogger<MailKitSmtpMailDeliveryService>.Instance
NullLogger<MailKitSmtpMailDeliveryService>.Instance,
Options.Create(x509ChainOptions)
);
var tcs = new TaskCompletionSource();
@ -234,7 +249,8 @@ public class MailKitSmtpMailDeliveryServiceTests
var mailKitDeliveryService = new MailKitSmtpMailDeliveryService(
globalSettings,
NullLogger<MailKitSmtpMailDeliveryService>.Instance
NullLogger<MailKitSmtpMailDeliveryService>.Instance,
Options.Create(new X509ChainOptions())
);
var tcs = new TaskCompletionSource();
@ -280,7 +296,8 @@ public class MailKitSmtpMailDeliveryServiceTests
var mailKitDeliveryService = new MailKitSmtpMailDeliveryService(
globalSettings,
NullLogger<MailKitSmtpMailDeliveryService>.Instance
NullLogger<MailKitSmtpMailDeliveryService>.Instance,
Options.Create(new X509ChainOptions())
);
var cts = new CancellationTokenSource(TimeSpan.FromSeconds(5));
@ -315,7 +332,8 @@ public class MailKitSmtpMailDeliveryServiceTests
var mailKitDeliveryService = new MailKitSmtpMailDeliveryService(
globalSettings,
NullLogger<MailKitSmtpMailDeliveryService>.Instance
NullLogger<MailKitSmtpMailDeliveryService>.Instance,
Options.Create(new X509ChainOptions())
);
var tcs = new TaskCompletionSource();
@ -381,7 +399,8 @@ public class MailKitSmtpMailDeliveryServiceTests
var mailKitDeliveryService = new MailKitSmtpMailDeliveryService(
globalSettings,
NullLogger<MailKitSmtpMailDeliveryService>.Instance
NullLogger<MailKitSmtpMailDeliveryService>.Instance,
Options.Create(new X509ChainOptions())
);
var tcs = new TaskCompletionSource();