diff --git a/Crypter.Core/Exceptions/HangfireJobException.cs b/Crypter.Core/Exceptions/HangfireJobException.cs
new file mode 100644
index 000000000..11611d089
--- /dev/null
+++ b/Crypter.Core/Exceptions/HangfireJobException.cs
@@ -0,0 +1,35 @@
+/*
+ * Copyright (C) 2023 Crypter File Transfer
+ *
+ * This file is part of the Crypter file transfer project.
+ *
+ * Crypter is free software: you can redistribute it and/or modify
+ * it under the terms of the GNU Affero General Public License as published by
+ * the Free Software Foundation, either version 3 of the License, or
+ * (at your option) any later version.
+ *
+ * The Crypter source code is distributed in the hope that it will be useful,
+ * but WITHOUT ANY WARRANTY; without even the implied warranty of
+ * MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+ * GNU Affero General Public License for more details.
+ *
+ * You should have received a copy of the GNU Affero General Public License
+ * along with this program.  If not, see <http://www.gnu.org/licenses/>.
+ *
+ * You can be released from the requirements of the aforementioned license
+ * by purchasing a commercial license. Buying such a license is mandatory
+ * as soon as you develop commercial activities involving the Crypter source
+ * code without disclosing the source code of your own applications.
+ *
+ * Contact the current copyright holder to discuss commercial license options.
+ */
+
+using System;
+
+namespace Crypter.Core.Exceptions;
+
+public class HangfireJobException : Exception
+{
+    public HangfireJobException(string message) : base(message)
+    { }
+}
diff --git a/Crypter.Core/Features/UserEmailVerification/Commands/SendVerificationEmailCommand.cs b/Crypter.Core/Features/UserEmailVerification/Commands/SendVerificationEmailCommand.cs
new file mode 100644
index 000000000..e20f9c4c7
--- /dev/null
+++ b/Crypter.Core/Features/UserEmailVerification/Commands/SendVerificationEmailCommand.cs
@@ -0,0 +1,87 @@
+/*
+ * Copyright (C) 2023 Crypter File Transfer
+ *
+ * This file is part of the Crypter file transfer project.
+ *
+ * Crypter is free software: you can redistribute it and/or modify
+ * it under the terms of the GNU Affero General Public License as published by
+ * the Free Software Foundation, either version 3 of the License, or
+ * (at your option) any later version.
+ *
+ * The Crypter source code is distributed in the hope that it will be useful,
+ * but WITHOUT ANY WARRANTY; without even the implied warranty of
+ * MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+ * GNU Affero General Public License for more details.
+ *
+ * You should have received a copy of the GNU Affero General Public License
+ * along with this program.  If not, see <http://www.gnu.org/licenses/>.
+ *
+ * You can be released from the requirements of the aforementioned license
+ * by purchasing a commercial license. Buying such a license is mandatory
+ * as soon as you develop commercial activities involving the Crypter source
+ * code without disclosing the source code of your own applications.
+ *
+ * Contact the current copyright holder to discuss commercial license options.
+ */
+
+using System;
+using System.Threading;
+using System.Threading.Tasks;
+using Crypter.Core.Models;
+using Crypter.Core.Services;
+using Crypter.Crypto.Common;
+using Crypter.DataAccess;
+using Crypter.DataAccess.Entities;
+using EasyMonads;
+using MediatR;
+
+namespace Crypter.Core.Features.UserEmailVerification.Commands;
+
+/// <summary>
+/// A command that will attempt to send a verification email to the provided
+/// user.
+///
+/// Returns 'true' if the email was successfully sent or if the user's current
+/// state is such that they should not receive a verification email.
+/// 
+/// Returns 'false' if the email should be sent, but failed to send.
+/// </summary>
+/// <param name="UserId"></param>
+public sealed record SendVerificationEmailCommand(Guid UserId) : IRequest<bool>;
+
+internal sealed class SendVerificationEmailCommandHandler
+    : IRequestHandler<SendVerificationEmailCommand, bool>
+{
+    private readonly ICryptoProvider _cryptoProvider;
+    private readonly DataContext _dataContext;
+    private readonly IEmailService _emailService;
+
+    public SendVerificationEmailCommandHandler(
+        ICryptoProvider cryptoProvider,
+        DataContext dataContext,
+        IEmailService emailService)
+    {
+        _cryptoProvider = cryptoProvider;
+        _dataContext = dataContext;
+        _emailService = emailService;
+    }
+    
+    public async Task<bool> Handle(SendVerificationEmailCommand request, CancellationToken cancellationToken)
+    {
+        return await UserEmailVerificationQueries
+            .GenerateVerificationParametersAsync(_dataContext, _cryptoProvider, request.UserId)
+            .BindAsync<UserEmailAddressVerificationParameters, bool>(async parameters =>
+            {
+                bool deliverySuccess = await _emailService.SendEmailVerificationAsync(parameters);
+                if (deliverySuccess)
+                {
+                    UserEmailVerificationEntity newEntity = new UserEmailVerificationEntity(parameters.UserId,
+                        parameters.VerificationCode, parameters.VerificationKey, DateTime.UtcNow);
+                    _dataContext.UserEmailVerifications.Add(newEntity);
+                    await _dataContext.SaveChangesAsync(CancellationToken.None);
+                }
+
+                return deliverySuccess;
+            }).SomeOrDefaultAsync(true);
+    }
+}
diff --git a/Crypter.Core/Features/UserEmailVerification/UserEmailVerificationCommands.cs b/Crypter.Core/Features/UserEmailVerification/UserEmailVerificationCommands.cs
index 981ae1236..4909c3dfc 100644
--- a/Crypter.Core/Features/UserEmailVerification/UserEmailVerificationCommands.cs
+++ b/Crypter.Core/Features/UserEmailVerification/UserEmailVerificationCommands.cs
@@ -26,7 +26,6 @@
 
 using System;
 using System.Threading.Tasks;
-using Crypter.Core.Models;
 using Crypter.DataAccess;
 using Crypter.DataAccess.Entities;
 using Microsoft.EntityFrameworkCore;
@@ -35,15 +34,6 @@ namespace Crypter.Core.Features.UserEmailVerification;
 
 internal static class UserEmailVerificationCommands
 {
-    internal static Task SaveVerificationParametersAsync(DataContext dataContext,
-        UserEmailAddressVerificationParameters parameters)
-    {
-        UserEmailVerificationEntity newEntity = new UserEmailVerificationEntity(parameters.UserId,
-            parameters.VerificationCode, parameters.VerificationKey, DateTime.UtcNow);
-        dataContext.UserEmailVerifications.Add(newEntity);
-        return dataContext.SaveChangesAsync();
-    }
-
     internal static async Task DeleteUserEmailVerificationEntity(DataContext dataContext, Guid userId, bool saveChanges)
     {
         UserEmailVerificationEntity foundEntity = await dataContext.UserEmailVerifications
diff --git a/Crypter.Core/Services/EmailService.cs b/Crypter.Core/Services/EmailService.cs
index dbbef6eea..e5a296d7d 100644
--- a/Crypter.Core/Services/EmailService.cs
+++ b/Crypter.Core/Services/EmailService.cs
@@ -34,6 +34,7 @@
 using MailKit.Security;
 using Microsoft.Extensions.DependencyInjection;
 using Microsoft.Extensions.DependencyInjection.Extensions;
+using Microsoft.Extensions.Logging;
 using Microsoft.Extensions.Options;
 using MimeKit;
 
@@ -63,11 +64,13 @@ public static void AddEmailService(this IServiceCollection services, Action<Emai
 
 public class EmailService : IEmailService
 {
-    private readonly EmailSettings Settings;
+    private readonly IOptions<EmailSettings> _settings;
+    private readonly ILogger<EmailService> _logger;
 
-    public EmailService(IOptions<EmailSettings> emailSettings)
+    public EmailService(IOptions<EmailSettings> emailSettings, ILogger<EmailService> logger)
     {
-        Settings = emailSettings.Value;
+        _settings = emailSettings;
+        _logger = logger;
     }
 
     /// <summary>
@@ -80,13 +83,13 @@ public EmailService(IOptions<EmailSettings> emailSettings)
     /// <returns></returns>
     public virtual async Task<bool> SendAsync(string subject, string message, EmailAddress recipient)
     {
-        if (!Settings.Enabled)
+        if (!_settings.Value.Enabled)
         {
             return true;
         }
 
         var mailMessage = new MimeMessage();
-        mailMessage.From.Add(MailboxAddress.Parse(Settings.From));
+        mailMessage.From.Add(MailboxAddress.Parse(_settings.Value.From));
         mailMessage.To.Add(MailboxAddress.Parse(recipient.Value));
         mailMessage.Subject = subject;
         mailMessage.Body = new TextPart("plain")
@@ -98,13 +101,13 @@ public virtual async Task<bool> SendAsync(string subject, string message, EmailA
 
         try
         {
-            await smtpClient.ConnectAsync(Settings.Host, Settings.Port, SecureSocketOptions.StartTls);
-            await smtpClient.AuthenticateAsync(Settings.Username, Settings.Password);
+            await smtpClient.ConnectAsync(_settings.Value.Host, _settings.Value.Port, SecureSocketOptions.StartTls);
+            await smtpClient.AuthenticateAsync(_settings.Value.Username, _settings.Value.Password);
             await smtpClient.SendAsync(mailMessage);
         }
         catch (Exception ex)
         {
-            Console.WriteLine(ex.Message);
+            _logger.LogError("An error occured while sending an email: {error}", ex.Message);
             return false;
         }
         finally
@@ -130,9 +133,7 @@ public async Task<bool> SendAccountRecoveryLinkAsync(UserRecoveryParameters para
     /// <summary>
     /// Send a verification email to the provided recipient.
     /// </summary>
-    /// <param name="emailAddress"></param>
-    /// <param name="verificationCode"></param>
-    /// <param name="ecdsaPrivateKey"></param>
+    /// <param name="parameters"></param>
     /// <remarks>This method is 'virtual' to enable some unit tests.</remarks>
     /// <returns></returns>
     public virtual async Task<bool> SendEmailVerificationAsync(UserEmailAddressVerificationParameters parameters)
diff --git a/Crypter.Core/Services/HangfireBackgroundService.cs b/Crypter.Core/Services/HangfireBackgroundService.cs
index a13346cac..83e8e988e 100644
--- a/Crypter.Core/Services/HangfireBackgroundService.cs
+++ b/Crypter.Core/Services/HangfireBackgroundService.cs
@@ -30,11 +30,12 @@
 using System.Threading.Tasks;
 using Crypter.Common.Enums;
 using Crypter.Common.Primitives;
+using Crypter.Core.Exceptions;
 using Crypter.Core.Features.AccountRecovery;
 using Crypter.Core.Features.Keys.Commands;
 using Crypter.Core.Features.Transfer;
 using Crypter.Core.Features.UserAuthentication;
-using Crypter.Core.Features.UserEmailVerification;
+using Crypter.Core.Features.UserEmailVerification.Commands;
 using Crypter.Core.Features.UserToken;
 using Crypter.Core.LinqExpressions;
 using Crypter.Core.Repositories;
@@ -43,13 +44,16 @@
 using Crypter.DataAccess.Entities;
 using EasyMonads;
 using Hangfire;
+using MediatR;
 using Microsoft.EntityFrameworkCore;
+using Microsoft.Extensions.Logging;
+using Unit = EasyMonads.Unit;
 
 namespace Crypter.Core.Services;
 
 public interface IHangfireBackgroundService
 {
-    Task SendEmailVerificationAsync(Guid userId);
+    Task<Unit> SendEmailVerificationAsync(Guid userId);
     Task SendTransferNotificationAsync(Guid itemId, TransferItemType itemType);
     Task SendRecoveryEmailAsync(string emailAddress);
 
@@ -85,35 +89,45 @@ Task DeleteTransferAsync(Guid itemId, TransferItemType itemType, TransferUserTyp
 public class HangfireBackgroundService : IHangfireBackgroundService
 {
     private readonly DataContext _dataContext;
+    private readonly ISender _sender;
     private readonly IBackgroundJobClient _backgroundJobClient;
     private readonly ICryptoProvider _cryptoProvider;
     private readonly IEmailService _emailService;
     private readonly ITransferRepository _transferRepository;
+    private readonly ILogger<HangfireBackgroundService> _logger;
 
-    private const int _accountRecoveryEmailExpirationMinutes = 30;
+    private const int AccountRecoveryEmailExpirationMinutes = 30;
 
     public HangfireBackgroundService(
-        DataContext dataContext, IBackgroundJobClient backgroundJobClient, ICryptoProvider cryptoProvider,
-        IEmailService emailService, ITransferRepository transferRepository)
+        DataContext dataContext,
+        ISender sender,
+        IBackgroundJobClient backgroundJobClient,
+        ICryptoProvider cryptoProvider,
+        IEmailService emailService,
+        ITransferRepository transferRepository,
+        ILogger<HangfireBackgroundService> logger)
     {
         _dataContext = dataContext;
+        _sender = sender;
         _backgroundJobClient = backgroundJobClient;
         _cryptoProvider = cryptoProvider;
         _emailService = emailService;
         _transferRepository = transferRepository;
+        _logger = logger;
     }
 
-    public Task SendEmailVerificationAsync(Guid userId)
+    public async Task<Unit> SendEmailVerificationAsync(Guid userId)
     {
-        return UserEmailVerificationQueries.GenerateVerificationParametersAsync(_dataContext, _cryptoProvider, userId)
-            .IfSomeAsync(async x =>
-            {
-                bool deliverySuccess = await _emailService.SendEmailVerificationAsync(x);
-                if (deliverySuccess)
-                {
-                    await UserEmailVerificationCommands.SaveVerificationParametersAsync(_dataContext, x);
-                }
-            });
+        var request = new SendVerificationEmailCommand(userId);
+        var result = await _sender.Send(request);
+        
+        if (!result)
+        {
+            _logger.LogError("Failed to send verification email for user: {userId}", userId);
+            throw new HangfireJobException($"{nameof(SendEmailVerificationAsync)} failed");
+        }
+
+        return Unit.Default;
     }
 
     public async Task SendTransferNotificationAsync(Guid itemId, TransferItemType itemType)
@@ -145,13 +159,13 @@ public Task SendRecoveryEmailAsync(string emailAddress)
             {
                 bool deliverySuccess =
                     await _emailService.SendAccountRecoveryLinkAsync(parameters,
-                        _accountRecoveryEmailExpirationMinutes);
+                        AccountRecoveryEmailExpirationMinutes);
                 if (deliverySuccess)
                 {
                     DateTime utcNow = DateTime.UtcNow;
                     await UserRecoveryCommands.SaveRecoveryParametersAsync(_dataContext, parameters, utcNow);
 
-                    DateTime recoveryExpiration = utcNow.AddMinutes(_accountRecoveryEmailExpirationMinutes);
+                    DateTime recoveryExpiration = utcNow.AddMinutes(AccountRecoveryEmailExpirationMinutes);
                     _backgroundJobClient.Schedule(() => DeleteRecoveryParametersAsync(parameters.UserId),
                         recoveryExpiration);
                 }
@@ -180,9 +194,10 @@ public Task DeleteRecoveryParametersAsync(Guid userId)
         return UserRecoveryCommands.DeleteRecoveryParametersAsync(_dataContext, userId);
     }
 
-    public Task<Unit> DeleteUserKeysAsync(Guid userId)
+    public async Task<Unit> DeleteUserKeysAsync(Guid userId)
     {
-        return DeleteUserKeysCommandHandler.HandleAsync(_dataContext, userId);
+        var request = new DeleteUserKeysCommand(userId);
+        return await _sender.Send(request);
     }
 
     public async Task<Unit> DeleteReceivedTransfersAsync(Guid userId)
diff --git a/Crypter.Test/Core_Tests/Services_Tests/EmailService_Tests.cs b/Crypter.Test/Core_Tests/Services_Tests/EmailService_Tests.cs
index 319815c46..fc9e18c24 100644
--- a/Crypter.Test/Core_Tests/Services_Tests/EmailService_Tests.cs
+++ b/Crypter.Test/Core_Tests/Services_Tests/EmailService_Tests.cs
@@ -28,6 +28,8 @@
 using Crypter.Common.Primitives;
 using Crypter.Core.Services;
 using Crypter.Core.Settings;
+using Microsoft.Extensions.DependencyInjection;
+using Microsoft.Extensions.Logging;
 using Microsoft.Extensions.Options;
 using NUnit.Framework;
 
@@ -37,18 +39,25 @@ namespace Crypter.Test.Core_Tests.Services_Tests;
 public class EmailService_Tests
 {
     private IOptions<EmailSettings> _defaultEmailSettings;
+    private ILogger<EmailService> _logger;
 
-    [OneTimeSetUp]
-    public void OneTimeSetup()
+    [SetUp]
+    public void Setup()
     {
         EmailSettings settings = new EmailSettings();
         _defaultEmailSettings = Options.Create(settings);
+        
+        var serviceProvider = new ServiceCollection()
+            .AddLogging()
+            .BuildServiceProvider();
+        var factory = serviceProvider.GetService<ILoggerFactory>();
+        _logger = factory.CreateLogger<EmailService>();
     }
 
     [Test]
     public async Task ServiceDisabled_SendAsync_ReturnsTrue()
     {
-        var sut = new EmailService(_defaultEmailSettings);
+        var sut = new EmailService(_defaultEmailSettings, _logger);
         var emailAddress = EmailAddress.From("jack@crypter.dev");
         var result = await sut.SendAsync("foo", "bar", emailAddress);
         Assert.IsTrue(result);
diff --git a/Crypter.Test/Core_Tests/Services_Tests/HangfireBackgroundService_Tests.cs b/Crypter.Test/Core_Tests/Services_Tests/HangfireBackgroundService_Tests.cs
index 05fa99662..b2c50ed53 100644
--- a/Crypter.Test/Core_Tests/Services_Tests/HangfireBackgroundService_Tests.cs
+++ b/Crypter.Test/Core_Tests/Services_Tests/HangfireBackgroundService_Tests.cs
@@ -34,8 +34,10 @@
 using Crypter.Crypto.Providers.Default;
 using Crypter.DataAccess;
 using Hangfire;
+using MediatR;
 using Microsoft.AspNetCore.Mvc.Testing;
 using Microsoft.Extensions.DependencyInjection;
+using Microsoft.Extensions.Logging;
 using Moq;
 using NUnit.Framework;
 
@@ -47,8 +49,10 @@ public class HangfireBackgroundService_Tests
     private WebApplicationFactory<Program> _factory;
     private IServiceScope _scope;
     private DataContext _dataContext;
-
+    private ISender _sender;
     private ICryptoProvider _cryptoProvider;
+    private ILogger<HangfireBackgroundService> _logger;
+    
     private Mock<IBackgroundJobClient> _backgroundJobClientMock;
     private Mock<IEmailService> _emailServiceMock;
     private Mock<ITransferRepository> _transferStorageMock;
@@ -66,6 +70,10 @@ public async Task SetupTestAsync()
 
         _scope = _factory.Services.CreateScope();
         _dataContext = _scope.ServiceProvider.GetRequiredService<DataContext>();
+        _sender = _scope.ServiceProvider.GetRequiredService<ISender>();
+        
+        var factory = _scope.ServiceProvider.GetRequiredService<ILoggerFactory>();
+        _logger = factory.CreateLogger<HangfireBackgroundService>();
     }
 
     [TearDown]
@@ -84,8 +92,8 @@ public async Task Verification_Email_Not_Sent_Without_Verification_Parameters()
                 It.IsAny<UserEmailAddressVerificationParameters>()))
             .ReturnsAsync((UserEmailAddressVerificationParameters parameters) => true);
 
-        HangfireBackgroundService sut = new HangfireBackgroundService(_dataContext, _backgroundJobClientMock.Object,
-            _cryptoProvider, _emailServiceMock.Object, _transferStorageMock.Object);
+        HangfireBackgroundService sut = new HangfireBackgroundService(_dataContext, _sender, _backgroundJobClientMock.Object,
+            _cryptoProvider, _emailServiceMock.Object, _transferStorageMock.Object, _logger);
         await sut.SendEmailVerificationAsync(Guid.NewGuid());
 
         _emailServiceMock.Verify(x => x.SendEmailVerificationAsync(It.IsAny<UserEmailAddressVerificationParameters>()),
@@ -101,8 +109,8 @@ public async Task Recovery_Email_Not_Sent_Without_Recovery_Parameters()
                 It.IsAny<int>()))
             .ReturnsAsync((UserRecoveryParameters parameters, int expirationMinutes) => true);
 
-        HangfireBackgroundService sut = new HangfireBackgroundService(_dataContext, _backgroundJobClientMock.Object,
-            _cryptoProvider, _emailServiceMock.Object, _transferStorageMock.Object);
+        HangfireBackgroundService sut = new HangfireBackgroundService(_dataContext, _sender, _backgroundJobClientMock.Object,
+            _cryptoProvider, _emailServiceMock.Object, _transferStorageMock.Object, _logger);
         await sut.SendRecoveryEmailAsync("foo@test.com");
 
         _emailServiceMock.Verify(