diff --git a/Jobs/BotAvatarJob.cs b/Jobs/BotAvatarJob.cs
index 308b3dc..b63deeb 100644
--- a/Jobs/BotAvatarJob.cs
+++ b/Jobs/BotAvatarJob.cs
@@ -27,10 +27,11 @@ public BotAvatarJob(DiscordSocketClient client, DB db, LogsService logsService)
 
     public async Task Execute(IJobExecutionContext context)
     {
+        CancellationToken cancellationToken = context.CancellationToken;
         try
         {
 
-            var setting = await _db.BotSettings.FirstOrDefaultAsync(s => s.Key == "BotAvatar");
+            var setting = await _db.BotSettings.FirstOrDefaultAsync(s => s.Key == "BotAvatar", cancellationToken);
             string current = setting?.Value ?? "unknown";
 
             bool isDecember = DateTime.UtcNow.Month == 12;
@@ -46,7 +47,9 @@ public async Task Execute(IJobExecutionContext context)
                 return;
 
             await using var fs = File.OpenRead(filePath);
-            await _client.CurrentUser.ModifyAsync(x => x.Avatar = new Image(fs));
+            await _client.CurrentUser.ModifyAsync(
+                x => x.Avatar = new Image(fs),
+                new RequestOptions { CancelToken = cancellationToken });
 
             if (setting == null)
             {
@@ -60,9 +63,13 @@ public async Task Execute(IJobExecutionContext context)
                 _db.BotSettings.Update(setting);
             }
 
-            await _db.SaveChangesAsync();
+            await _db.SaveChangesAsync(cancellationToken);
             _logsService.Log($"Quartz Job - Bot avatar updated to {targetKey}");
         }
+        catch (OperationCanceledException) when (cancellationToken.IsCancellationRequested)
+        {
+            throw;
+        }
         catch (Exception ex)
         {
             _logsService.Log($"Quartz Job - Error updating bot avatar: {ex}");
diff --git a/Morpheus.Tests/BotAvatarJobTests.cs b/Morpheus.Tests/BotAvatarJobTests.cs
new file mode 100644
index 0000000..1268aa6
--- /dev/null
+++ b/Morpheus.Tests/BotAvatarJobTests.cs
@@ -0,0 +1,56 @@
+using Discord.WebSocket;
+using Microsoft.Data.Sqlite;
+using Microsoft.EntityFrameworkCore;
+using Morpheus.Database;
+using Morpheus.Jobs;
+using Morpheus.Services;
+using Quartz;
+using System.Reflection;
+
+namespace Morpheus.Tests;
+
+public class BotAvatarJobTests
+{
+    [Fact]
+    public async Task Execute_WhenCanceledBeforeLookup_PropagatesCancellation()
+    {
+        await using SqliteConnection connection = new("Data Source=:memory:");
+        await connection.OpenAsync();
+        DbContextOptions<DB> options = new DbContextOptionsBuilder<DB>()
+            .UseSqlite(connection)
+            .Options;
+        await using DB db = new(options);
+        await db.Database.EnsureCreatedAsync();
+        using DiscordSocketClient discordClient = new();
+
+        BotAvatarJob job = new(discordClient, db, new LogsService(new LogQueue()));
+        using CancellationTokenSource cancellation = new();
+        await cancellation.CancelAsync();
+
+        IJobExecutionContext context = CreateContext(cancellation.Token);
+
+        await Assert.ThrowsAnyAsync<OperationCanceledException>(() => job.Execute(context));
+    }
+
+    private static IJobExecutionContext CreateContext(CancellationToken cancellationToken)
+    {
+        JobExecutionContextProxy.CurrentCancellationToken = cancellationToken;
+        return DispatchProxy.Create<IJobExecutionContext, JobExecutionContextProxy>();
+    }
+
+    private class JobExecutionContextProxy : DispatchProxy
+    {
+        public static CancellationToken CurrentCancellationToken { get; set; }
+
+        protected override object? Invoke(MethodInfo? targetMethod, object?[]? args)
+        {
+            if (targetMethod?.ReturnType == typeof(CancellationToken))
+                return CurrentCancellationToken;
+
+            Type returnType = targetMethod?.ReturnType ?? typeof(void);
+            return returnType == typeof(void) || !returnType.IsValueType
+                ? null
+                : Activator.CreateInstance(returnType);
+        }
+    }
+}