diff --git a/LeaderboardBackend.Test/Features/Users/AccountConfirmationTests.cs b/LeaderboardBackend.Test/Features/Users/AccountConfirmationTests.cs
index e6930d98..0c3187db 100644
--- a/LeaderboardBackend.Test/Features/Users/AccountConfirmationTests.cs
+++ b/LeaderboardBackend.Test/Features/Users/AccountConfirmationTests.cs
@@ -107,7 +107,7 @@ public async Task ResendConfirmation_Success()
         emailSenderMock.Verify(x =>
             x.EnqueueEmailAsync(
                 "email1",
-                AccountController.ACCOUNT_CONFIRMATION_EMAIL_TITLE,
+                "Confirmation",
                 It.IsAny<string>()
             ),
             Times.Once()
diff --git a/LeaderboardBackend/Controllers/AccountController.cs b/LeaderboardBackend/Controllers/AccountController.cs
index 1bfda655..9648643f 100644
--- a/LeaderboardBackend/Controllers/AccountController.cs
+++ b/LeaderboardBackend/Controllers/AccountController.cs
@@ -5,6 +5,7 @@
 using LeaderboardBackend.Services;
 using Microsoft.AspNetCore.Authorization;
 using Microsoft.AspNetCore.Mvc;
+using OneOf;
 
 namespace LeaderboardBackend.Controllers;
 
@@ -13,8 +14,6 @@ namespace LeaderboardBackend.Controllers;
 public class AccountController : ControllerBase
 {
     private readonly IUserService _userService;
-    // TODO: Finalise the title
-    public const string ACCOUNT_CONFIRMATION_EMAIL_TITLE = "Confirmation";
 
     public AccountController(IUserService userService)
     {
@@ -123,6 +122,7 @@ public async Task<ActionResult<LoginResponse>> Login([FromBody] LoginRequest req
     ///     Resends the account confirmation link.
     /// </summary>
     /// <param name="authService">IAuthService dependency.</param>
+    /// <param name="confirmationService">IConfirmationService dependency.</param>
     /// <param name="emailSender">EmailSender dependency.</param>
     /// <response code="200">The request was sent successfully.</response>
     /// <response code="400">
@@ -131,9 +131,6 @@ public async Task<ActionResult<LoginResponse>> Login([FromBody] LoginRequest req
     /// <response code="401">
     ///     The request doesn't contain a valid session token.
     /// </response>
-    /// <response code="404">
-    ///     The `User` the request is for wasn't found.
-    /// </response>
     /// <response code="409">
     ///     A `User` with the specified username or email already exists.<br/><br/>
     ///     Validation error codes by property:
@@ -142,13 +139,16 @@ public async Task<ActionResult<LoginResponse>> Login([FromBody] LoginRequest req
     ///     - **Email**:
     ///       - **EmailAlreadyUsed**: the email is already in use
     /// </response>
+    /// <response code="500">
+    ///     Internal server error.
+    /// </response>
     [HttpPost("confirm")]
     [ProducesResponseType(StatusCodes.Status200OK)]
     [ProducesResponseType(StatusCodes.Status400BadRequest)]
     [ProducesResponseType(StatusCodes.Status401Unauthorized)]
-    [ProducesResponseType(StatusCodes.Status404NotFound)]
     [ProducesResponseType(StatusCodes.Status409Conflict)]
     [ProducesResponseType(StatusCodes.Status429TooManyRequests)]
+    [ProducesResponseType(StatusCodes.Status500InternalServerError)]
     public async Task<ActionResult> ResendConfirmation(
         [FromServices] IAuthService authService,
         [FromServices] IConfirmationService confirmationService,
@@ -157,40 +157,23 @@ [FromServices] IEmailSender emailSender
     {
         // TODO: Handle rate limiting (429 case) - zysim
 
-        Guid? userId = authService.GetUserIdFromClaims(HttpContext.User);
-
-        if (userId is null)
-        {
-            return Unauthorized();
-        }
-
-        User? user = await _userService.GetUserById(userId ?? Guid.Empty);
+        GetUserResult result = await _userService.GetRegisteredUserFromClaims(HttpContext.User);
 
-        if (user is null)
+        if (result.TryPickT0(out User user, out OneOf<BadCredentials, UserNotFound, BadRole> errors))
         {
-            return NotFound();
+            CreateUserConfirmationResult confirmationResult = await confirmationService.CreateConfirmation(user);
+            return confirmationResult.Match(
+                confirmation => Ok(),
+                dbCreateFailed => StatusCode(StatusCodes.Status500InternalServerError),
+                dbTimedOut => StatusCode(StatusCodes.Status500InternalServerError)
+            );
         }
 
-        if (user.Role is not UserRole.Registered)
-        {
-            return Conflict();
-        }
-
-        UserConfirmation confirmation = await confirmationService.CreateConfirmation(user);
-
-#pragma warning disable CS4014 // Suppress no 'await' call
-        emailSender.EnqueueEmailAsync(
-            user.Email,
-            ACCOUNT_CONFIRMATION_EMAIL_TITLE,
-            // TODO: Generate confirmation link
-            GenerateAccountConfirmationEmailBody(user, confirmation)
+        return errors.Match(
+            badCredentials => Unauthorized(),
+            // Shouldn't be possible; throw 500
+            notFound => StatusCode(StatusCodes.Status500InternalServerError),
+            badRole => Conflict()
         );
-#pragma warning restore CS4014
-
-        return Ok();
     }
-
-    // TODO: Finalise message contents
-    private string GenerateAccountConfirmationEmailBody(User user, UserConfirmation confirmation) =>
-        $@"Hi {user.Username},<br/><br/>Click <a href=""/confirm-account?code={Convert.ToBase64String(confirmation.Id.ToByteArray())}"">here</a> to confirm your account.";
 }
diff --git a/LeaderboardBackend/Services/IConfirmationService.cs b/LeaderboardBackend/Services/IConfirmationService.cs
index 938a7372..15d7b0c9 100644
--- a/LeaderboardBackend/Services/IConfirmationService.cs
+++ b/LeaderboardBackend/Services/IConfirmationService.cs
@@ -1,9 +1,16 @@
 using LeaderboardBackend.Models.Entities;
+using OneOf;
 
 namespace LeaderboardBackend.Services;
 
 public interface IConfirmationService
 {
     Task<UserConfirmation?> GetConfirmationById(Guid id);
-    Task<UserConfirmation> CreateConfirmation(User user);
+    Task<CreateUserConfirmationResult> CreateConfirmation(User user, CancellationToken token = default);
 }
+
+[GenerateOneOf]
+public partial class CreateUserConfirmationResult : OneOfBase<UserConfirmation, DbCreateFailed, DbCreateTimedOut> { };
+
+public readonly record struct DbCreateFailed();
+public readonly record struct DbCreateTimedOut();
diff --git a/LeaderboardBackend/Services/Impl/ConfirmationService.cs b/LeaderboardBackend/Services/Impl/ConfirmationService.cs
index 7ad62a17..2f29cf62 100644
--- a/LeaderboardBackend/Services/Impl/ConfirmationService.cs
+++ b/LeaderboardBackend/Services/Impl/ConfirmationService.cs
@@ -1,14 +1,17 @@
 using LeaderboardBackend.Models.Entities;
+using Microsoft.EntityFrameworkCore;
 
 namespace LeaderboardBackend.Services;
 
 public class ConfirmationService : IConfirmationService
 {
     private readonly ApplicationContext _applicationContext;
+    private readonly IEmailSender _emailSender;
 
-    public ConfirmationService(ApplicationContext applicationContext)
+    public ConfirmationService(ApplicationContext applicationContext, IEmailSender emailSender)
     {
         _applicationContext = applicationContext;
+        _emailSender = emailSender;
     }
 
     public async Task<UserConfirmation?> GetConfirmationById(Guid id)
@@ -16,7 +19,7 @@ public ConfirmationService(ApplicationContext applicationContext)
         return await _applicationContext.UserConfirmations.FindAsync(id);
     }
 
-    public async Task<UserConfirmation> CreateConfirmation(User user)
+    public async Task<CreateUserConfirmationResult> CreateConfirmation(User user, CancellationToken token = default)
     {
         UserConfirmation newConfirmation =
             new()
@@ -26,8 +29,33 @@ public async Task<UserConfirmation> CreateConfirmation(User user)
 
         _applicationContext.UserConfirmations.Add(newConfirmation);
 
-        await _applicationContext.SaveChangesAsync();
+        try
+        {
+            await _applicationContext.SaveChangesAsync(token);
+        }
+        catch (DbUpdateException)
+        {
+            return new DbCreateFailed();
+        }
+        catch (OperationCanceledException)
+        {
+            return new DbCreateTimedOut();
+        }
+
+#pragma warning disable CS4014 // Suppress no 'await' call
+        _emailSender.EnqueueEmailAsync(
+            user.Email,
+            // TODO: Finalise the title
+            "Confirmation",
+            // TODO: Generate confirmation link
+            GenerateAccountConfirmationEmailBody(user, newConfirmation)
+        );
+#pragma warning restore CS4014
 
         return newConfirmation;
     }
+
+    // TODO: Finalise message contents
+    private string GenerateAccountConfirmationEmailBody(User user, UserConfirmation confirmation) =>
+        $@"Hi {user.Username},<br/><br/>Click <a href=""/confirm-account?code={Convert.ToBase64String(confirmation.Id.ToByteArray())}"">here</a> to confirm your account.";
 }