diff --git a/Morpheus.Tests/LogsWriterServiceTests.cs b/Morpheus.Tests/LogsWriterServiceTests.cs
index 0b237a3..1092e22 100644
--- a/Morpheus.Tests/LogsWriterServiceTests.cs
+++ b/Morpheus.Tests/LogsWriterServiceTests.cs
@@ -45,6 +45,43 @@ public async Task ExecuteAsync_RetriesBatchAfterTransientPersistenceFailure()
         await writer.StopAsync(CancellationToken.None);
     }
 
+    [Fact]
+    public async Task ExecuteAsync_RetriesFinalBatchAfterTransientPersistenceFailure()
+    {
+        await using SqliteConnection connection = new("Data Source=:memory:");
+        await connection.OpenAsync();
+
+        DbContextOptions<DB> options = new DbContextOptionsBuilder<DB>()
+            .UseSqlite(connection)
+            .Options;
+        await using DB observer = new(options);
+        await observer.Database.EnsureCreatedAsync();
+        FailureState failureState = new();
+
+        ServiceCollection services = new();
+        services.AddScoped<DB>(_ => new FailingDb(options, failureState));
+        using ServiceProvider provider = services.BuildServiceProvider();
+
+        LogQueue queue = new(capacity: 10);
+        Assert.True(queue.TryEnqueue(
+            LogsService.CreateGeneralLog("shutdown retry", Discord.LogSeverity.Warning)));
+        LogsWriterService writer = new(queue, provider.GetRequiredService<IServiceScopeFactory>());
+
+        await writer.StartAsync(CancellationToken.None);
+
+        DateTime deadline = DateTime.UtcNow.AddSeconds(2);
+        while (queue.Reader.Count > 0 && DateTime.UtcNow < deadline)
+            await Task.Delay(10);
+        Assert.Equal(0, queue.Reader.Count);
+
+        await writer.StopAsync(CancellationToken.None);
+
+        Assert.Equal(1, await observer.Logs.CountAsync());
+        Assert.Equal(
+            LogsService.FormatGeneralLog("shutdown retry", Discord.LogSeverity.Warning),
+            (await observer.Logs.SingleAsync()).Message);
+    }
+
     private sealed class FailureState
     {
         public bool FailNextSave { get; set; } = true;
@@ -54,6 +91,8 @@ private sealed class FailingDb(DbContextOptions<DB> options, FailureState state)
     {
         public override Task<int> SaveChangesAsync(CancellationToken cancellationToken = default)
         {
+            cancellationToken.ThrowIfCancellationRequested();
+
             if (state.FailNextSave)
             {
                 state.FailNextSave = false;
diff --git a/Services/LogsWriterService.cs b/Services/LogsWriterService.cs
index 6e35bc9..29f3e3e 100644
--- a/Services/LogsWriterService.cs
+++ b/Services/LogsWriterService.cs
@@ -8,6 +8,7 @@ namespace Morpheus.Services;
 public sealed class LogsWriterService(LogQueue logQueue, IServiceScopeFactory scopeFactory) : BackgroundService
 {
     private const int BatchSize = 50;
+    private const int MaxFinalFlushAttempts = 3;
     private static readonly TimeSpan BatchDelay = TimeSpan.FromMilliseconds(250);
 
     protected override async Task ExecuteAsync(CancellationToken stoppingToken)
@@ -52,11 +53,24 @@ protected override async Task ExecuteAsync(CancellationToken stoppingToken)
         }
         finally
         {
+            int failedFlushAttempts = 0;
             while (true)
             {
                 DrainAvailable(batch);
-                if (batch.Count == 0 || !await FlushAsync(batch, CancellationToken.None))
+                if (batch.Count == 0)
                     break;
+
+                if (await FlushAsync(batch, CancellationToken.None))
+                {
+                    failedFlushAttempts = 0;
+                    continue;
+                }
+
+                failedFlushAttempts++;
+                if (failedFlushAttempts >= MaxFinalFlushAttempts)
+                    break;
+
+                await Task.Delay(BatchDelay);
             }
         }
     }