JobTrackerApi.Tests/EmailSendAttemptStoreTests.cs

@@ -58,12 +58,49 @@ public sealed class EmailSendAttemptStoreTests
             property.Name.Contains("Recipient", StringComparison.OrdinalIgnoreCase));
     }
 
+    [Fact]
+    public async Task Restart_recovery_is_tenant_visible_idempotent_and_never_requeues_delivery()
+    {
+        await using var fixture = await Fixture.CreateAsync();
+        var ownerOne = fixture.Store("user-1");
+        var ownerTwo = fixture.Store("user-2");
+        var oldSending = await ownerOne.CreateAsync(new(fixture.JobId, "gmail", Guid.NewGuid().ToString(), Hash('e')), default);
+        var oldPending = await ownerTwo.CreateAsync(new(fixture.OtherJobId, "microsoft", Guid.NewGuid().ToString(), Hash('f')), default);
+        Assert.Equal(1, await ownerOne.BeginAsync(oldSending.Attempt.Id, default));
+
+        fixture.Time.Advance(EmailSendAttemptStore.AbandonedAge + TimeSpan.FromSeconds(1));
+        var freshPending = await ownerOne.CreateAsync(new(fixture.JobId, "gmail", Guid.NewGuid().ToString(), Hash('1')), default);
+        var freshSending = await ownerTwo.CreateAsync(new(fixture.OtherJobId, "microsoft", Guid.NewGuid().ToString(), Hash('2')), default);
+        Assert.Equal(1, await ownerTwo.BeginAsync(freshSending.Attempt.Id, default));
+
+        var recovered = await fixture.Store(null).ReconcileAbandonedAsync(default);
+        var repeated = await fixture.Store(null).ReconcileAbandonedAsync(default);
+
+        Assert.Equal(new EmailSendAttemptRecoveryResult(1, 1), recovered);
+        Assert.Equal(new EmailSendAttemptRecoveryResult(0, 0), repeated);
+        Assert.Equal(EmailSendStatuses.Uncertain, (await ownerOne.GetAsync(oldSending.Attempt.Id, default))!.Status);
+        Assert.Equal(EmailSendStatuses.Failed, (await ownerTwo.GetAsync(oldPending.Attempt.Id, default))!.Status);
+        Assert.Equal(EmailSendStatuses.Pending, (await ownerOne.GetAsync(freshPending.Attempt.Id, default))!.Status);
+        Assert.Equal(EmailSendStatuses.Sending, (await ownerTwo.GetAsync(freshSending.Attempt.Id, default))!.Status);
+
+        var userOneNotifications = await fixture.Notifications("user-1").ListAsync(10, default);
+        var userTwoNotifications = await fixture.Notifications("user-2").ListAsync(10, default);
+        Assert.Single(userOneNotifications);
+        Assert.Single(userTwoNotifications);
+        Assert.Equal("email.send.uncertain", userOneNotifications[0].Kind);
+        Assert.Equal("email.send.stopped", userTwoNotifications[0].Kind);
+        Assert.DoesNotContain("gmail", userOneNotifications[0].Message, StringComparison.OrdinalIgnoreCase);
+        Assert.DoesNotContain("microsoft", userTwoNotifications[0].Message, StringComparison.OrdinalIgnoreCase);
+    }
+
     private static string Hash(char value) => new(value, 64);
 
-    private sealed class Fixture(SqliteConnection connection, DbContextOptions<JobTrackerContext> options, int jobId) : IAsyncDisposable
+    private sealed class Fixture(SqliteConnection connection, DbContextOptions<JobTrackerContext> options, int jobId, int otherJobId) : IAsyncDisposable
     {
         private readonly List<JobTrackerContext> contexts = new();
+        public ManualTimeProvider Time { get; } = new(new DateTimeOffset(2026, 8, 10, 12, 0, 0, TimeSpan.Zero));
         public int JobId { get; } = jobId;
+        public int OtherJobId { get; } = otherJobId;
 
         public static async Task<Fixture> CreateAsync()
         {
@@ -78,17 +115,31 @@ public sealed class EmailSendAttemptStoreTests
             var job = new JobApplication { JobTitle = "Backend", CompanyId = company.Id, OwnerUserId = "user-1" };
             db.JobApplications.Add(job);
             await db.SaveChangesAsync();
-            return new Fixture(connection, options, job.Id);
+            await using var otherDb = CreateDb(options, "user-2");
+            var otherCompany = new Company { Name = "Other", OwnerUserId = "user-2" };
+            otherDb.Companies.Add(otherCompany);
+            await otherDb.SaveChangesAsync();
+            var otherJob = new JobApplication { JobTitle = "Frontend", CompanyId = otherCompany.Id, OwnerUserId = "user-2" };
+            otherDb.JobApplications.Add(otherJob);
+            await otherDb.SaveChangesAsync();
+            return new Fixture(connection, options, job.Id, otherJob.Id);
         }
 
-        public EmailSendAttemptStore Store(string userId)
+        public EmailSendAttemptStore Store(string? userId)
         {
             var db = CreateDb(options, userId);
             contexts.Add(db);
-            return new EmailSendAttemptStore(db, TimeProvider.System);
+            return new EmailSendAttemptStore(db, Time);
         }
 
-        private static JobTrackerContext CreateDb(DbContextOptions<JobTrackerContext> options, string userId)
+        public UserNotificationStore Notifications(string userId)
+        {
+            var db = CreateDb(options, userId);
+            contexts.Add(db);
+            return new UserNotificationStore(db, Time);
+        }
+
+        private static JobTrackerContext CreateDb(DbContextOptions<JobTrackerContext> options, string? userId)
         {
             var currentUser = new Mock<ICurrentUserService>();
             currentUser.SetupGet(service => service.UserId).Returns(userId);
@@ -101,4 +152,11 @@ public sealed class EmailSendAttemptStoreTests
             await connection.DisposeAsync();
         }
     }
+
+    private sealed class ManualTimeProvider(DateTimeOffset now) : TimeProvider
+    {
+        public DateTimeOffset UtcNow { get; private set; } = now;
+        public override DateTimeOffset GetUtcNow() => UtcNow;
+        public void Advance(TimeSpan duration) => UtcNow += duration;
+    }
 }

JobTrackerApi/Program.cs

@@ -168,6 +168,7 @@ builder.Services.AddHostedService<DailyExportHostedService>();
 builder.Services.AddHostedService<JobEnrichmentHostedService>();
 builder.Services.AddHostedService<SummarizerProbeHostedService>();
 builder.Services.AddHostedService<AiOperationHostedService>();
+builder.Services.AddHostedService<EmailSendAttemptRecoveryHostedService>();
 
 builder.Services.AddHttpClient("jobimport")
     .ConfigurePrimaryHttpMessageHandler(() => new HttpClientHandler

JobTrackerApi/Services/EmailSendAttemptRecoveryHostedService.cs

@@ -0,0 +1,44 @@
+namespace JobTrackerApi.Services;
+
+public sealed class EmailSendAttemptRecoveryHostedService(
+    IServiceScopeFactory scopes,
+    IStartupReadiness startupReadiness,
+    ILogger<EmailSendAttemptRecoveryHostedService> logger) : BackgroundService
+{
+    protected override async Task ExecuteAsync(CancellationToken stoppingToken)
+    {
+        await startupReadiness.WaitUntilReadyAsync(stoppingToken);
+        while (!stoppingToken.IsCancellationRequested)
+        {
+            try
+            {
+                await using var scope = scopes.CreateAsyncScope();
+                var result = await scope.ServiceProvider.GetRequiredService<EmailSendAttemptStore>()
+                    .ReconcileAbandonedAsync(stoppingToken);
+                if (result.FailedPending > 0 || result.UncertainSending > 0)
+                {
+                    logger.LogWarning(
+                        "Recovered abandoned email attempts: failedPending={FailedPending}, uncertainSending={UncertainSending}. No provider retry was attempted.",
+                        result.FailedPending, result.UncertainSending);
+                }
+            }
+            catch (OperationCanceledException) when (stoppingToken.IsCancellationRequested)
+            {
+                break;
+            }
+            catch (Exception ex)
+            {
+                logger.LogError(ex, "Email send-attempt recovery failed; provider delivery was not attempted.");
+            }
+
+            try
+            {
+                await Task.Delay(TimeSpan.FromMinutes(5), stoppingToken);
+            }
+            catch (OperationCanceledException)
+            {
+                break;
+            }
+        }
+    }
+}

JobTrackerApi/Services/EmailSendAttemptStore.cs

@@ -6,11 +6,13 @@ namespace JobTrackerApi.Services;
 
 public sealed record CreateEmailSendAttempt(int JobApplicationId, string Provider, string ClientRequestId, string PayloadHash);
 public sealed record EmailSendAttemptCreation(EmailSendAttempt Attempt, bool Created);
+public sealed record EmailSendAttemptRecoveryResult(int FailedPending, int UncertainSending);
 
 public sealed class EmailSendConflictException(string message) : InvalidOperationException(message);
 
 public sealed class EmailSendAttemptStore(JobTrackerContext db, TimeProvider timeProvider)
 {
+    public static readonly TimeSpan AbandonedAge = TimeSpan.FromMinutes(15);
     private DateTime UtcNow => timeProvider.GetUtcNow().UtcDateTime;
 
     public Task<EmailSendAttempt?> GetAsync(Guid id, CancellationToken cancellationToken)
@@ -74,6 +76,58 @@ public sealed class EmailSendAttemptStore(JobTrackerContext db, TimeProvider tim
     public Task<int> MarkUncertainAsync(Guid id, string failureCategory, CancellationToken cancellationToken) =>
         CompleteAsync(id, EmailSendStatuses.Uncertain, null, failureCategory, cancellationToken);
 
+    public async Task<EmailSendAttemptRecoveryResult> ReconcileAbandonedAsync(CancellationToken cancellationToken)
+    {
+        var now = UtcNow;
+        var cutoff = now - AbandonedAge;
+        var candidates = await db.EmailSendAttempts.IgnoreQueryFilters().AsNoTracking()
+            .Where(item =>
+                (item.Status == EmailSendStatuses.Pending && item.CreatedAtUtc <= cutoff) ||
+                (item.Status == EmailSendStatuses.Sending && (item.StartedAtUtc ?? item.CreatedAtUtc) <= cutoff))
+            .Select(item => new { item.Id, item.OwnerUserId, item.Status })
+            .ToListAsync(cancellationToken);
+        if (candidates.Count == 0) return new EmailSendAttemptRecoveryResult(0, 0);
+
+        await using var transaction = db.Database.IsRelational()
+            ? await db.Database.BeginTransactionAsync(cancellationToken)
+            : null;
+        var failedPending = 0;
+        var uncertainSending = 0;
+        foreach (var candidate in candidates)
+        {
+            var failed = candidate.Status == EmailSendStatuses.Pending;
+            var terminalStatus = failed ? EmailSendStatuses.Failed : EmailSendStatuses.Uncertain;
+            var failureCategory = failed ? "process_stopped_before_delivery" : "process_interrupted";
+            var affected = await db.EmailSendAttempts.IgnoreQueryFilters()
+                .Where(item => item.Id == candidate.Id && item.Status == candidate.Status &&
+                    (failed ? item.CreatedAtUtc <= cutoff : (item.StartedAtUtc ?? item.CreatedAtUtc) <= cutoff))
+                .ExecuteUpdateAsync(setters => setters
+                    .SetProperty(item => item.Status, terminalStatus)
+                    .SetProperty(item => item.FailureCategory, failureCategory)
+                    .SetProperty(item => item.CompletedAtUtc, now), cancellationToken);
+            if (affected != 1) continue;
+
+            if (failed) failedPending++;
+            else uncertainSending++;
+            db.UserNotifications.Add(new UserNotification
+            {
+                Id = Guid.NewGuid(),
+                OwnerUserId = candidate.OwnerUserId,
+                Kind = failed ? "email.send.stopped" : "email.send.uncertain",
+                Title = failed ? "Email send stopped" : "Check email delivery",
+                Message = failed
+                    ? "An email attempt stopped before provider delivery. Review the draft before trying again."
+                    : "Email delivery could not be confirmed after an interruption. Check the provider Sent folder and do not resend automatically.",
+                LinkPath = "/correspondence",
+                CreatedAtUtc = now,
+            });
+        }
+
+        await db.SaveChangesAsync(cancellationToken);
+        if (transaction is not null) await transaction.CommitAsync(cancellationToken);
+        return new EmailSendAttemptRecoveryResult(failedPending, uncertainSending);
+    }
+
     private Task<int> CompleteAsync(Guid id, string status, string? providerMessageId, string? failureCategory, CancellationToken cancellationToken)
     {
         EnsureOwnerScope();