diff --git a/src/Core/Platform/X509ChainCustomization/PostConfigureX509ChainOptions.cs b/src/Core/Platform/X509ChainCustomization/PostConfigureX509ChainOptions.cs
new file mode 100644
index 0000000000..3361201093
--- /dev/null
+++ b/src/Core/Platform/X509ChainCustomization/PostConfigureX509ChainOptions.cs
@@ -0,0 +1,94 @@
+#nullable enable
+
+using System.Security.Cryptography.X509Certificates;
+using Microsoft.Extensions.Options;
+using Microsoft.Extensions.Logging;
+using Microsoft.Extensions.Hosting;
+using Bit.Core.Settings;
+
+namespace Bit.Core.Platform.X509ChainCustomization;
+
+internal sealed class PostConfigureX509ChainOptions : IPostConfigureOptions<X509ChainOptions>
+{
+    const string CertificateSearchPattern = "*.crt";
+
+    private readonly ILogger<PostConfigureX509ChainOptions> _logger;
+    private readonly IHostEnvironment _hostEnvironment;
+    private readonly GlobalSettings _globalSettings;
+
+    public PostConfigureX509ChainOptions(
+        ILogger<PostConfigureX509ChainOptions> logger,
+        IHostEnvironment hostEnvironment,
+        GlobalSettings globalSettings)
+    {
+        _logger = logger;
+        _hostEnvironment = hostEnvironment;
+        _globalSettings = globalSettings;
+    }
+
+    public void PostConfigure(string? name, X509ChainOptions options)
+    {
+        if (name != Options.DefaultName)
+        {
+            return;
+        }
+
+        // We only allow this setting to be configured on self host.
+        if (!_globalSettings.SelfHosted)
+        {
+            options.AdditionalCustomTrustCertificatesDirectory = null;
+            return;
+        }
+
+        if (options.AdditionalCustomTrustCertificates != null)
+        {
+            // Additional certificates were added directly, this overwrites the need to
+            // read them from the directory.
+            _logger.LogInformation(
+                "Additional custom trust certificates were added directly, skipping loading them from '{Directory}'",
+                options.AdditionalCustomTrustCertificatesDirectory
+            );
+            return;
+        }
+
+        if (string.IsNullOrEmpty(options.AdditionalCustomTrustCertificatesDirectory))
+        {
+            return;
+        }
+
+        if (!Directory.Exists(options.AdditionalCustomTrustCertificatesDirectory))
+        {
+            // The default directory is volume mounted via the default Bitwarden setup process.
+            // If the directory doesn't exist it could indicate a error in configuration but this
+            // directory is never expected in a normal development environment so lower the log
+            // level in that case.
+            var logLevel = _hostEnvironment.IsDevelopment()
+                ? LogLevel.Debug
+                : LogLevel.Warning;
+            _logger.Log(
+                logLevel,
+                "An additional custom trust certificate directory was given '{Directory}' but that directory does not exist.",
+                options.AdditionalCustomTrustCertificatesDirectory
+            );
+            return;
+        }
+
+        var certificates = new List<X509Certificate2>();
+
+        foreach (var certFile in Directory.EnumerateFiles(options.AdditionalCustomTrustCertificatesDirectory, CertificateSearchPattern))
+        {
+            certificates.Add(new X509Certificate2(certFile));
+        }
+
+        if (options.AdditionalCustomTrustCertificatesDirectory != X509ChainOptions.DefaultAdditionalCustomTrustCertificatesDirectory && certificates.Count == 0)
+        {
+            // They have intentionally given us a non-default directory but there weren't certificates, that is odd.
+            _logger.LogWarning(
+                "No additional custom trust certificates were found in '{Directory}'",
+                options.AdditionalCustomTrustCertificatesDirectory
+            );
+        }
+
+        options.AdditionalCustomTrustCertificates = certificates;
+    }
+}
diff --git a/src/Core/Platform/X509ChainCustomization/X509ChainCustomizationServiceCollectionExtensions.cs b/src/Core/Platform/X509ChainCustomization/X509ChainCustomizationServiceCollectionExtensions.cs
new file mode 100644
index 0000000000..45de2c5460
--- /dev/null
+++ b/src/Core/Platform/X509ChainCustomization/X509ChainCustomizationServiceCollectionExtensions.cs
@@ -0,0 +1,53 @@
+using Bit.Core.Platform.X509ChainCustomization;
+using Microsoft.Extensions.Options;
+using Microsoft.Extensions.DependencyInjection.Extensions;
+
+namespace Microsoft.Extensions.DependencyInjection;
+
+/// <summary>
+/// Extension methods for setting up the ability to provide customization to how TLS works in an <see cref="IServiceCollection"/>.
+/// </summary>
+public static class X509ChainCustomizationServiceCollectionExtensions
+{
+    /// <summary>
+    /// Configures X509ChainPolicy customization through the root level <c>TlsOptions</c> configuration section
+    /// and configures the primary <see cref="HttpMessageHandler"/> to use custom certificate validation
+    /// when customized to do so.
+    /// </summary>
+    /// <param name="services">The <see cref="IServiceCollection"/>.</param>
+    /// <returns>The <see cref="IServiceCollection"/> for additional chaining.</returns>
+    public static IServiceCollection AddX509ChainCustomization(this IServiceCollection services)
+    {
+        ArgumentNullException.ThrowIfNull(services);
+
+        services.AddOptions<X509ChainOptions>()
+            .BindConfiguration(nameof(X509ChainOptions));
+
+        // Use TryAddEnumerable to make sure `PostConfigureTlsOptions` isn't added multiple
+        // times even if this method is called multiple times.
+        services.TryAddEnumerable(ServiceDescriptor.Singleton<IPostConfigureOptions<X509ChainOptions>, PostConfigureX509ChainOptions>());
+
+        services.AddHttpClient()
+            .ConfigureHttpClientDefaults(builder =>
+            {
+                builder.ConfigurePrimaryHttpMessageHandler(sp =>
+                {
+                    var tlsOptions = sp.GetRequiredService<IOptions<X509ChainOptions>>().Value;
+
+                    var handler = new HttpClientHandler();
+
+                    if (tlsOptions.TryGetCustomRemoteCertificateValidationCallback(out var callback))
+                    {
+                        handler.ServerCertificateCustomValidationCallback = (sender, certificate, chain, errors) =>
+                        {
+                            return callback(certificate, chain, errors);
+                        };
+                    }
+
+                    return handler;
+                });
+            });
+
+        return services;
+    }
+}
diff --git a/src/Core/Platform/X509ChainCustomization/X509ChainOptions.cs b/src/Core/Platform/X509ChainCustomization/X509ChainOptions.cs
new file mode 100644
index 0000000000..19cbd73ae3
--- /dev/null
+++ b/src/Core/Platform/X509ChainCustomization/X509ChainOptions.cs
@@ -0,0 +1,72 @@
+#nullable enable
+
+using System.Diagnostics.CodeAnalysis;
+using System.Net.Security;
+using System.Security.Cryptography.X509Certificates;
+
+namespace Bit.Core.Platform.X509ChainCustomization;
+
+/// <summary>
+/// Allows for customization of 
+/// </summary>
+public sealed class X509ChainOptions
+{
+    // This is the directory that we historically used to allow certificates be added inside our container
+    // and then on start of the container we would move them to `/usr/local/share/ca-certificates/` and call
+    // `update-ca-certificates` but since that operation requires root we can't do it in a rootless container.
+    // Ref: https://github.com/bitwarden/server/blob/67d7d685a619a5fc413f8532dacb09681ee5c956/src/Api/entrypoint.sh#L38-L41
+    public const string DefaultAdditionalCustomTrustCertificatesDirectory = "/etc/bitwarden/ca-certificates/";
+
+    /// <summary>
+    /// A directory where additional certificates should be read from and included in <see cref="X509ChainPolicy.CustomTrustStore"/>.
+    /// </summary>
+    /// <remarks>
+    /// Only certificates suffixed with <c>*.crt</c> will be read. If <see cref="AdditionalCustomTrustCertificates"/> is
+    /// set, then this directory will not be read from.
+    /// </remarks>
+    public string? AdditionalCustomTrustCertificatesDirectory { get; set; } = DefaultAdditionalCustomTrustCertificatesDirectory;
+
+    /// <summary>
+    /// A list of additional certificates that should be included in <see cref="X509ChainPolicy.CustomTrustStore"/>.
+    /// </summary>
+    /// <remarks>
+    /// If this value is set manually, then <see cref="AdditionalCustomTrustCertificatesDirectory"/> will be ignored.
+    /// </remarks>
+    public List<X509Certificate2>? AdditionalCustomTrustCertificates { get; set; }
+
+    /// <summary>
+    /// Attempts to retrieve a custom remote certificate validation callback.
+    /// </summary>
+    /// <param name="callback"></param>
+    /// <returns>Returns <see langword="true"/> when we have custom remote certification that should be added,
+    /// <see langword="false"/> when no custom validation is needed and the default validation callback should
+    /// be used instead.
+    /// </returns>
+    [MemberNotNullWhen(true, nameof(AdditionalCustomTrustCertificates))]
+    public bool TryGetCustomRemoteCertificateValidationCallback(
+        [MaybeNullWhen(false)]out Func<X509Certificate2?, X509Chain?, SslPolicyErrors, bool> callback)
+    {
+        callback = null;
+        if (AdditionalCustomTrustCertificates == null || AdditionalCustomTrustCertificates.Count == 0)
+        {
+            return false;
+        }
+
+        // Ref: https://github.com/dotnet/runtime/issues/39835#issuecomment-663020581
+        callback = (certificate, chain, errors) =>
+        {
+            if (chain == null || certificate == null)
+            {
+                return false;
+            }
+
+            chain.ChainPolicy.TrustMode = X509ChainTrustMode.CustomRootTrust;
+            foreach (var additionalCertificate in AdditionalCustomTrustCertificates)
+            {
+                chain.ChainPolicy.CustomTrustStore.Add(additionalCertificate);
+            }
+            return chain.Build(certificate);
+        };
+        return true;
+    }
+}
diff --git a/src/Core/Services/Implementations/MailKitSmtpMailDeliveryService.cs b/src/Core/Services/Implementations/MailKitSmtpMailDeliveryService.cs
index dc4e89aa23..f9a6762772 100644
--- a/src/Core/Services/Implementations/MailKitSmtpMailDeliveryService.cs
+++ b/src/Core/Services/Implementations/MailKitSmtpMailDeliveryService.cs
@@ -1,7 +1,10 @@
-using Bit.Core.Settings;
+using System.Security.Cryptography.X509Certificates;
+using Bit.Core.Platform.X509ChainCustomization;
+using Bit.Core.Settings;
 using Bit.Core.Utilities;
 using MailKit.Net.Smtp;
 using Microsoft.Extensions.Logging;
+using Microsoft.Extensions.Options;
 using MimeKit;
 
 namespace Bit.Core.Services;
@@ -10,12 +13,14 @@ public class MailKitSmtpMailDeliveryService : IMailDeliveryService
 {
     private readonly GlobalSettings _globalSettings;
     private readonly ILogger<MailKitSmtpMailDeliveryService> _logger;
+    private readonly X509ChainOptions _x509CertificateCustomization;
     private readonly string _replyDomain;
     private readonly string _replyEmail;
 
     public MailKitSmtpMailDeliveryService(
         GlobalSettings globalSettings,
-        ILogger<MailKitSmtpMailDeliveryService> logger)
+        ILogger<MailKitSmtpMailDeliveryService> logger,
+        IOptions<X509ChainOptions> tlsOptions)
     {
         if (globalSettings.Mail?.Smtp?.Host == null)
         {
@@ -31,6 +36,7 @@ public class MailKitSmtpMailDeliveryService : IMailDeliveryService
 
         _globalSettings = globalSettings;
         _logger = logger;
+        _x509CertificateCustomization = tlsOptions.Value;
     }
 
     public async Task SendEmailAsync(Models.Mail.MailMessage message)
@@ -75,6 +81,13 @@ public class MailKitSmtpMailDeliveryService : IMailDeliveryService
             {
                 client.ServerCertificateValidationCallback = (s, c, h, e) => true;
             }
+            else if (_x509CertificateCustomization.TryGetCustomRemoteCertificateValidationCallback(out var callback))
+            {
+                client.ServerCertificateValidationCallback = (sender, cert, chain, errors) =>
+                {
+                    return callback(new X509Certificate2(cert), chain, errors);
+                };
+            }
 
             if (!_globalSettings.Mail.Smtp.StartTls && !_globalSettings.Mail.Smtp.Ssl &&
                 _globalSettings.Mail.Smtp.Port == 25)
diff --git a/test/Core.IntegrationTest/MailKitSmtpMailDeliveryServiceTests.cs b/test/Core.IntegrationTest/MailKitSmtpMailDeliveryServiceTests.cs
index db2b945fda..7914a6d147 100644
--- a/test/Core.IntegrationTest/MailKitSmtpMailDeliveryServiceTests.cs
+++ b/test/Core.IntegrationTest/MailKitSmtpMailDeliveryServiceTests.cs
@@ -3,9 +3,11 @@ using System.Security.Cryptography.X509Certificates;
 using Bit.Core.Models.Mail;
 using Bit.Core.Services;
 using Bit.Core.Settings;
+using Bit.Core.Platform.TlsCustomization;
 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;
@@ -100,7 +102,8 @@ public class MailKitSmtpMailDeliveryServiceTests
 
         var mailKitDeliveryService = new MailKitSmtpMailDeliveryService(
             globalSettings,
-            NullLogger<MailKitSmtpMailDeliveryService>.Instance
+            NullLogger<MailKitSmtpMailDeliveryService>.Instance,
+            Options.Create(new X509CertificateCustomizationOptions())
         );
 
         await Assert.ThrowsAsync<SslHandshakeException>(
@@ -113,7 +116,7 @@ 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 +133,18 @@ public class MailKitSmtpMailDeliveryServiceTests
             gs.Mail.Smtp.Ssl = true;
         });
 
-        // TODO: Setup custom location and save self signed cert there.
-        // await SaveCertAsync("./my-location", _selfSignedCert);
+        var tlsOptions = new X509CertificateCustomizationOptions
+        {
+            AdditionalCustomTrustCertificates =
+            [
+                _selfSignedCert,
+            ],
+        };
 
         var mailKitDeliveryService = new MailKitSmtpMailDeliveryService(
             globalSettings,
-            NullLogger<MailKitSmtpMailDeliveryService>.Instance
+            NullLogger<MailKitSmtpMailDeliveryService>.Instance,
+            Options.Create(tlsOptions)
         );
 
         var tcs = new TaskCompletionSource();
@@ -162,7 +171,7 @@ 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 +188,19 @@ 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 tlsOptions = new X509CertificateCustomizationOptions
+        {
+            AdditionalCustomTrustCertificates =
+            [
+                _selfSignedCert,
+                CreateSelfSignedCert("example.com"),
+            ],
+        };
 
         var mailKitDeliveryService = new MailKitSmtpMailDeliveryService(
             globalSettings,
-            NullLogger<MailKitSmtpMailDeliveryService>.Instance
+            NullLogger<MailKitSmtpMailDeliveryService>.Instance,
+            Options.Create(tlsOptions)
         );
 
         var tcs = new TaskCompletionSource();
@@ -234,7 +247,8 @@ public class MailKitSmtpMailDeliveryServiceTests
 
         var mailKitDeliveryService = new MailKitSmtpMailDeliveryService(
             globalSettings,
-            NullLogger<MailKitSmtpMailDeliveryService>.Instance
+            NullLogger<MailKitSmtpMailDeliveryService>.Instance,
+            Options.Create(new X509CertificateCustomizationOptions())
         );
 
         var tcs = new TaskCompletionSource();
@@ -280,7 +294,8 @@ public class MailKitSmtpMailDeliveryServiceTests
 
         var mailKitDeliveryService = new MailKitSmtpMailDeliveryService(
             globalSettings,
-            NullLogger<MailKitSmtpMailDeliveryService>.Instance
+            NullLogger<MailKitSmtpMailDeliveryService>.Instance,
+            Options.Create(new X509CertificateCustomizationOptions())
         );
 
         var cts = new CancellationTokenSource(TimeSpan.FromSeconds(5));
@@ -315,7 +330,8 @@ public class MailKitSmtpMailDeliveryServiceTests
 
         var mailKitDeliveryService = new MailKitSmtpMailDeliveryService(
             globalSettings,
-            NullLogger<MailKitSmtpMailDeliveryService>.Instance
+            NullLogger<MailKitSmtpMailDeliveryService>.Instance,
+            Options.Create(new X509CertificateCustomizationOptions())
         );
 
         var tcs = new TaskCompletionSource();
@@ -381,7 +397,8 @@ public class MailKitSmtpMailDeliveryServiceTests
 
         var mailKitDeliveryService = new MailKitSmtpMailDeliveryService(
             globalSettings,
-            NullLogger<MailKitSmtpMailDeliveryService>.Instance
+            NullLogger<MailKitSmtpMailDeliveryService>.Instance,
+            Options.Create(new X509CertificateCustomizationOptions())
         );
 
         var tcs = new TaskCompletionSource();
diff --git a/test/Core.Test/Platform/X509ChainCustomization/X509ChainCustomizationServiceCollectionExtensionsTests.cs b/test/Core.Test/Platform/X509ChainCustomization/X509ChainCustomizationServiceCollectionExtensionsTests.cs
new file mode 100644
index 0000000000..2af9b7cc8a
--- /dev/null
+++ b/test/Core.Test/Platform/X509ChainCustomization/X509ChainCustomizationServiceCollectionExtensionsTests.cs
@@ -0,0 +1,137 @@
+using System.Security.Cryptography;
+using System.Security.Cryptography.X509Certificates;
+using Bit.Core.Platform.X509ChainCustomization;
+using Bit.Core.Settings;
+using Microsoft.Extensions.Configuration;
+using Microsoft.Extensions.DependencyInjection;
+using Microsoft.Extensions.Hosting;
+using Microsoft.Extensions.Options;
+using NSubstitute;
+using Xunit;
+
+namespace Bit.Core.Test.Platform.TlsCustomization;
+
+public class X509ChainCustomizationServiceCollectionExtensionsTests
+{
+    private static X509Certificate2 CreateSelfSignedCert(string commonName)
+    {
+        using var rsa = RSA.Create(2048);
+        var certRequest = new CertificateRequest($"CN={commonName}", rsa, HashAlgorithmName.SHA256, RSASignaturePadding.Pkcs1);
+        return certRequest.CreateSelfSigned(DateTimeOffset.UtcNow, DateTimeOffset.UtcNow.AddYears(1));
+    }
+
+    [Fact]
+    public async Task OptionsPatternReturnsCachedValue()
+    {
+        var tempDir = Directory.CreateTempSubdirectory("certs");
+        
+        var tempCert = Path.Combine(tempDir.FullName, "test.crt");
+        await File.WriteAllBytesAsync(tempCert, CreateSelfSignedCert("localhost").Export(X509ContentType.Cert));
+
+        var services = CreateServices((gs, environment, config) =>
+        {
+            gs.SelfHosted = true;
+
+            environment.EnvironmentName = "Development";
+
+            config["X509ChainOptions:AdditionalCustomTrustCertificatesDirectory"] = tempDir.FullName;
+        });
+        
+        // Create options once
+        var firstOptions = services.GetRequiredService<IOptions<X509ChainOptions>>().Value;
+
+        Assert.NotNull(firstOptions.AdditionalCustomTrustCertificates);
+        var cert = Assert.Single(firstOptions.AdditionalCustomTrustCertificates);
+        Assert.Equal("CN=localhost", cert.Subject);
+
+        // Since the second resolution should have cached values, deleting the file during operation
+        // should have no impact.
+        File.Delete(tempCert);
+
+        // This is expected to be a cached version and doesn't actually need to go and read the file system
+        var secondOptions = services.GetRequiredService<IOptions<X509ChainOptions>>().Value;
+        Assert.Same(firstOptions, secondOptions);
+
+        // This is the same reference as the first one so it shouldn't be different but just in case.
+        Assert.NotNull(secondOptions.AdditionalCustomTrustCertificates);
+        Assert.Single(secondOptions.AdditionalCustomTrustCertificates);
+    }
+
+    [Fact]
+    public async Task DoesNotProvideCustomCallbackOnCloud()
+    {
+        var tempDir = Directory.CreateTempSubdirectory("certs");
+        
+        var tempCert = Path.Combine(tempDir.FullName, "test.crt");
+        await File.WriteAllBytesAsync(tempCert, CreateSelfSignedCert("localhost").Export(X509ContentType.Cert));
+
+        var options = CreateOptions((gs, environment, config) =>
+        {
+            gs.SelfHosted = false;
+
+            environment.EnvironmentName = "Development";
+
+            config["X509ChainOptions:AdditionalCustomTrustCertificatesDirectory"] = tempDir.FullName;
+        });
+
+        Assert.False(options.TryGetCustomRemoteCertificateValidationCallback(out _));
+    }
+
+    [Fact]
+    public async Task ManuallyAddingOptionsTakesPrecedence()
+    {
+        var tempDir = Directory.CreateTempSubdirectory("certs");
+        
+        var tempCert = Path.Combine(tempDir.FullName, "test.crt");
+        await File.WriteAllBytesAsync(tempCert, CreateSelfSignedCert("localhost").Export(X509ContentType.Cert));
+
+        var options = CreateOptions((gs, environment, config) =>
+        {
+            gs.SelfHosted = false;
+
+            environment.EnvironmentName = "Development";
+
+            config["X509ChainOptions:AdditionalCustomTrustCertificatesDirectory"] = tempDir.FullName;
+        }, services =>
+        {
+            services.Configure<X509ChainOptions>(options =>
+            {
+                options.AdditionalCustomTrustCertificates = [CreateSelfSignedCert("example.com")];
+            });
+        });
+
+        Assert.True(options.TryGetCustomRemoteCertificateValidationCallback(out var callback));
+        var cert = Assert.Single(options.AdditionalCustomTrustCertificates);
+        Assert.Equal("CN=example.com", cert.Subject);
+    }
+
+    private static X509ChainOptions CreateOptions(Action<GlobalSettings, IHostEnvironment, Dictionary<string, string>> configure, Action<IServiceCollection>? after = null)
+    {
+        var services = CreateServices(configure, after);
+        return services.GetRequiredService<IOptions<X509ChainOptions>>().Value;
+    }
+
+    private static IServiceProvider CreateServices(Action<GlobalSettings, IHostEnvironment, Dictionary<string, string>> configure, Action<IServiceCollection>? after = null)
+    {
+        var globalSettings = new GlobalSettings();
+        var hostEnvironment = Substitute.For<IHostEnvironment>();
+        var config = new Dictionary<string, string>();
+
+        configure(globalSettings, hostEnvironment, config);
+
+        var services = new ServiceCollection();
+        services.AddSingleton(globalSettings);
+        services.AddSingleton(hostEnvironment);
+        services.AddSingleton<IConfiguration>(
+            new ConfigurationBuilder()
+                .AddInMemoryCollection(config)
+                .Build()
+        );
+
+        services.AddX509ChainCustomization();
+
+        after?.Invoke(services);
+
+        return services.BuildServiceProvider();
+    }
+}
diff --git a/test/Core.Test/Services/HandlebarsMailServiceTests.cs b/test/Core.Test/Services/HandlebarsMailServiceTests.cs
index 89d9a211e0..35c2f8fe3b 100644
--- a/test/Core.Test/Services/HandlebarsMailServiceTests.cs
+++ b/test/Core.Test/Services/HandlebarsMailServiceTests.cs
@@ -4,9 +4,11 @@ using Bit.Core.AdminConsole.Entities.Provider;
 using Bit.Core.Auth.Entities;
 using Bit.Core.Auth.Models.Business;
 using Bit.Core.Entities;
+using Bit.Core.Platform.X509ChainCustomization;
 using Bit.Core.Services;
 using Bit.Core.Settings;
 using Microsoft.Extensions.Logging;
+using Microsoft.Extensions.Options;
 using NSubstitute;
 using Xunit;
 
@@ -136,7 +138,7 @@ public class HandlebarsMailServiceTests
             SiteName = "Bitwarden",
         };
 
-        var mailDeliveryService = new MailKitSmtpMailDeliveryService(globalSettings, Substitute.For<ILogger<MailKitSmtpMailDeliveryService>>());
+        var mailDeliveryService = new MailKitSmtpMailDeliveryService(globalSettings, Substitute.For<ILogger<MailKitSmtpMailDeliveryService>>(), Options.Create(new X509ChainOptions()));
 
         var handlebarsService = new HandlebarsMailService(globalSettings, mailDeliveryService, new BlockingMailEnqueuingService());
 
diff --git a/test/Core.Test/Services/MailKitSmtpMailDeliveryServiceTests.cs b/test/Core.Test/Services/MailKitSmtpMailDeliveryServiceTests.cs
index 4e7e36fe02..06ee99dbef 100644
--- a/test/Core.Test/Services/MailKitSmtpMailDeliveryServiceTests.cs
+++ b/test/Core.Test/Services/MailKitSmtpMailDeliveryServiceTests.cs
@@ -1,6 +1,8 @@
-using Bit.Core.Services;
+using Bit.Core.Platform.X509ChainCustomization;
+using Bit.Core.Services;
 using Bit.Core.Settings;
 using Microsoft.Extensions.Logging;
+using Microsoft.Extensions.Options;
 using NSubstitute;
 using Xunit;
 
@@ -23,7 +25,8 @@ public class MailKitSmtpMailDeliveryServiceTests
 
         _sut = new MailKitSmtpMailDeliveryService(
             _globalSettings,
-            _logger
+            _logger,
+            Options.Create(new X509ChainOptions())
         );
     }