diff --git a/.github/workflows/dotnet.yml b/.github/workflows/dotnet.yml
index d52612f..9a91db5 100644
--- a/.github/workflows/dotnet.yml
+++ b/.github/workflows/dotnet.yml
@@ -2,9 +2,9 @@
 name: .NET Build and Test
 on:
   push:
-    branches: [main]
+    branches: [ main ]
   pull_request:
-    branches: [main]
+    branches: [ main ]
 permissions:
   packages: write
 jobs:
diff --git a/.github/workflows/push_to_live.yml b/.github/workflows/push_to_live.yml
index 67447a4..155246a 100644
--- a/.github/workflows/push_to_live.yml
+++ b/.github/workflows/push_to_live.yml
@@ -2,9 +2,9 @@
 name: Push to Live
 on:
   workflow_run:
-    workflows: [.NET Build and Test]
-    types: [completed]
-    branches: [main]
+    workflows: [ .NET Build and Test ]
+    types: [ completed ]
+    branches: [ main ]
 jobs:
   build-and-deploy:
     runs-on: ubuntu-latest
diff --git a/Bottomly.ServiceDefaults/Extensions.cs b/Bottomly.ServiceDefaults/Extensions.cs
index 5e47062..7fc0291 100644
--- a/Bottomly.ServiceDefaults/Extensions.cs
+++ b/Bottomly.ServiceDefaults/Extensions.cs
@@ -92,7 +92,7 @@ private static TBuilder AddOpenTelemetryExporters<TBuilder>(this TBuilder builde
         if (!string.IsNullOrEmpty(builder.Configuration["APPLICATIONINSIGHTS_CONNECTION_STRING"]))
         {
             builder.Services.AddOpenTelemetry()
-               .UseAzureMonitor();
+                .UseAzureMonitor();
         }
 
         return builder;
diff --git a/Bottomly.Tests/Bottomly.Tests.csproj b/Bottomly.Tests/Bottomly.Tests.csproj
index f92ffc2..07afc25 100644
--- a/Bottomly.Tests/Bottomly.Tests.csproj
+++ b/Bottomly.Tests/Bottomly.Tests.csproj
@@ -9,24 +9,24 @@
     </PropertyGroup>
 
     <ItemGroup>
-        <PackageReference Include="coverlet.collector" Version="6.0.4" />
-        <PackageReference Include="Meziantou.Extensions.Logging.Xunit" Version="1.0.25" />
-        <PackageReference Include="Microsoft.Extensions.Configuration.UserSecrets" Version="10.0.5" />
-        <PackageReference Include="Microsoft.Extensions.Options" Version="10.0.3" />
-        <PackageReference Include="Microsoft.NET.Test.Sdk" Version="17.14.1" />
-        <PackageReference Include="Moq" Version="4.20.72" />
-        <PackageReference Include="Shouldly" Version="4.3.0" />
-        <PackageReference Include="Testcontainers.MongoDb" Version="4.11.0" />
-        <PackageReference Include="xunit" Version="2.9.3" />
-        <PackageReference Include="xunit.runner.visualstudio" Version="3.1.4" />
+        <PackageReference Include="coverlet.collector" Version="6.0.4"/>
+        <PackageReference Include="Meziantou.Extensions.Logging.Xunit" Version="1.0.25"/>
+        <PackageReference Include="Microsoft.Extensions.Configuration.UserSecrets" Version="10.0.5"/>
+        <PackageReference Include="Microsoft.Extensions.Options" Version="10.0.3"/>
+        <PackageReference Include="Microsoft.NET.Test.Sdk" Version="17.14.1"/>
+        <PackageReference Include="Moq" Version="4.20.72"/>
+        <PackageReference Include="Shouldly" Version="4.3.0"/>
+        <PackageReference Include="Testcontainers.MongoDb" Version="4.11.0"/>
+        <PackageReference Include="xunit" Version="2.9.3"/>
+        <PackageReference Include="xunit.runner.visualstudio" Version="3.1.4"/>
     </ItemGroup>
 
     <ItemGroup>
-        <Using Include="Xunit" />
+        <Using Include="Xunit"/>
     </ItemGroup>
 
     <ItemGroup>
-        <ProjectReference Include="..\Bottomly\Bottomly.csproj" />
+        <ProjectReference Include="..\Bottomly\Bottomly.csproj"/>
     </ItemGroup>
 
 </Project>
\ No newline at end of file
diff --git a/Bottomly.Tests/Commands/AddKarmaCommandTests.cs b/Bottomly.Tests/Commands/AddKarmaCommandTests.cs
index 87850ec..40a731b 100644
--- a/Bottomly.Tests/Commands/AddKarmaCommandTests.cs
+++ b/Bottomly.Tests/Commands/AddKarmaCommandTests.cs
@@ -1,6 +1,7 @@
 using Bottomly.Commands;
 using Bottomly.Models;
 using Bottomly.Repositories;
+using Microsoft.Extensions.Logging.Abstractions;
 using Moq;
 using Shouldly;
 
@@ -11,15 +12,16 @@ public class AddKarmaCommandTests
     private readonly AddKarmaCommand _command;
     private readonly Mock<IKarmaRepository> _mockRepo = new();
 
-    public AddKarmaCommandTests() => _command = new AddKarmaCommand(_mockRepo.Object);
+    public AddKarmaCommandTests() => _command = new AddKarmaCommand(_mockRepo.Object, NullLogger<AddKarmaCommand>.Instance);
 
     [Fact]
     public async Task ExecuteAsync_AwardsKarma_PersistsToRepository()
     {
         _mockRepo.Setup(r => r.AddAsync(It.IsAny<Karma>())).Returns(Task.CompletedTask);
 
-        await _command.ExecuteAsync("alice", "bob", "great job", KarmaType.PozzyPoz);
+        var result = await _command.ExecuteAsync("alice", "bob", "great job", KarmaType.PozzyPoz);
 
+        result.ShouldBeOfType<AddKarmaSuccessResult>();
         _mockRepo.Verify(r => r.AddAsync(It.Is<Karma>(k =>
             k.AwardedToUsername == "alice" &&
             k.AwardedByUsername == "bob" &&
@@ -28,15 +30,31 @@ public async Task ExecuteAsync_AwardsKarma_PersistsToRepository()
     }
 
     [Fact]
-    public async Task ExecuteAsync_SelfPositiveKarma_ThrowsInvalidOperation() =>
-        await Should.ThrowAsync<InvalidOperationException>(() =>
-            _command.ExecuteAsync("alice", "alice", "", KarmaType.PozzyPoz));
+    public async Task ExecuteAsync_SelfPositiveKarma_ReturnsSelfAwardResult()
+    {
+        var result = await _command.ExecuteAsync("alice", "alice", "", KarmaType.PozzyPoz);
+
+        result.ShouldBeOfType<AddKarmaSelfAwardResult>();
+    }
 
     [Fact]
-    public async Task ExecuteAsync_SelfNegativeKarma_DoesNotThrow()
+    public async Task ExecuteAsync_SelfNegativeKarma_ReturnsSuccessResult()
     {
         _mockRepo.Setup(r => r.AddAsync(It.IsAny<Karma>())).Returns(Task.CompletedTask);
 
-        await Should.NotThrowAsync(() => _command.ExecuteAsync("alice", "alice", "", KarmaType.NeggyNeg));
+        var result = await _command.ExecuteAsync("alice", "alice", "", KarmaType.NeggyNeg);
+
+        result.ShouldBeOfType<AddKarmaSuccessResult>();
+    }
+
+    [Fact]
+    public async Task ExecuteAsync_RepositoryThrows_ReturnsErrorResult()
+    {
+        _mockRepo.Setup(r => r.AddAsync(It.IsAny<Karma>())).ThrowsAsync(new Exception("DB error"));
+
+        var result = await _command.ExecuteAsync("alice", "bob", "great job", KarmaType.PozzyPoz);
+
+        var error = result.ShouldBeOfType<AddKarmaErrorResult>();
+        error.Error.ShouldBe("DB error");
     }
 }
\ No newline at end of file
diff --git a/Bottomly.Tests/Commands/GiphyCommandTests.cs b/Bottomly.Tests/Commands/GiphyCommandTests.cs
index 43e2a12..16ed148 100644
--- a/Bottomly.Tests/Commands/GiphyCommandTests.cs
+++ b/Bottomly.Tests/Commands/GiphyCommandTests.cs
@@ -25,14 +25,16 @@ public async Task ExecuteAsync_EmptyInput_ReturnsBadInputResult()
     [Fact]
     public async Task ExecuteAsync_WithResult_ReturnsSuccessResult()
     {
-        const string json = """{"data":{"url":"https://giphy.com/gifs/funny-cat"}}""";
+        const string json =
+            """{"data":{"images":{"original":{"url":"https://media.giphy.com/media/funny-cat/giphy.gif"}}}}""";
         var options = Options.Create(new BottomlyOptions { GiphyApiKey = "test" });
-        var command = new GiphyCommand(TestHelpers.CreateHttpClientFactory(json), options, NullLogger<GiphyCommand>.Instance);
+        var command = new GiphyCommand(TestHelpers.CreateHttpClientFactory(json), options,
+            NullLogger<GiphyCommand>.Instance);
 
         var result = await command.ExecuteAsync("cat");
 
         var successResult = result.ShouldBeOfType<GiphySuccessResult>();
-        successResult.Url.ShouldBe("https://giphy.com/gifs/funny-cat");
+        successResult.Url.ShouldBe("https://media.giphy.com/media/funny-cat/giphy.gif");
     }
 
     [Fact]
@@ -40,7 +42,8 @@ public async Task ExecuteAsync_EmptyDataArray_ReturnsEmptyResult()
     {
         const string json = """{"data":[]}""";
         var options = Options.Create(new BottomlyOptions { GiphyApiKey = "test" });
-        var command = new GiphyCommand(TestHelpers.CreateHttpClientFactory(json), options, NullLogger<GiphyCommand>.Instance);
+        var command = new GiphyCommand(TestHelpers.CreateHttpClientFactory(json), options,
+            NullLogger<GiphyCommand>.Instance);
 
         var result = await command.ExecuteAsync("obscuresearch");
 
diff --git a/Bottomly.Tests/Commands/ImageSearchCommandTests.cs b/Bottomly.Tests/Commands/ImageSearchCommandTests.cs
index 20708b8..0db1e25 100644
--- a/Bottomly.Tests/Commands/ImageSearchCommandTests.cs
+++ b/Bottomly.Tests/Commands/ImageSearchCommandTests.cs
@@ -15,11 +15,9 @@ public class ImageSearchCommandTests
         Microsoft.Extensions.Options.Options.Create(new BottomlyOptions { BraveApiKey = "fake-key" });
 
     private static ImageSearchCommand CreateCommand(string responseJson,
-        HttpStatusCode statusCode = HttpStatusCode.OK)
-    {
-        return new ImageSearchCommand(Options, TestHelpers.CreateHttpClientFactory(responseJson, statusCode),
+        HttpStatusCode statusCode = HttpStatusCode.OK) =>
+        new(Options, TestHelpers.CreateHttpClientFactory(responseJson, statusCode),
             NullLogger<ImageSearchCommand>.Instance);
-    }
 
     [Fact]
     public async Task ExecuteAsync_EmptyInput_ReturnsEmptySearchTermErrorResult()
diff --git a/Bottomly.Tests/Commands/Integration/ImageSearchCommandIntegrationTests.cs b/Bottomly.Tests/Commands/Integration/ImageSearchCommandIntegrationTests.cs
index 39514b9..8e2a3e7 100644
--- a/Bottomly.Tests/Commands/Integration/ImageSearchCommandIntegrationTests.cs
+++ b/Bottomly.Tests/Commands/Integration/ImageSearchCommandIntegrationTests.cs
@@ -29,10 +29,8 @@ public class ImageSearchCommandIntegrationTests
 
     private readonly ILogger<ImageSearchCommand> _logger;
 
-    public ImageSearchCommandIntegrationTests(ITestOutputHelper outputHelper)
-    {
+    public ImageSearchCommandIntegrationTests(ITestOutputHelper outputHelper) =>
         _logger = XUnitLogger.CreateLogger<ImageSearchCommand>(outputHelper);
-    }
 
     private static string? ApiKey => Configuration["bottomly_brave_api_key"];
 
@@ -47,11 +45,6 @@ private ImageSearchCommand CreateCommand()
         }), factory, _logger);
     }
 
-    private sealed class DefaultHttpClientFactory : IHttpClientFactory
-    {
-        public HttpClient CreateClient(string name) => new();
-    }
-
     [Fact]
     public async Task ExecuteAsync_EmptyInput_ReturnsEmptySearchTermErrorResult()
     {
@@ -97,4 +90,9 @@ public async Task ExecuteAsync_KnownSearchTerm_ReturnsRelevantResult()
         searchResult.Link.ShouldNotBeNullOrEmpty();
         searchResult.Link.ShouldStartWith("http");
     }
+
+    private sealed class DefaultHttpClientFactory : IHttpClientFactory
+    {
+        public HttpClient CreateClient(string name) => new();
+    }
 }
\ No newline at end of file
diff --git a/Bottomly.Tests/Commands/Integration/SearchCommandIntegrationTests.cs b/Bottomly.Tests/Commands/Integration/SearchCommandIntegrationTests.cs
index 72f4b84..d1fd6ed 100644
--- a/Bottomly.Tests/Commands/Integration/SearchCommandIntegrationTests.cs
+++ b/Bottomly.Tests/Commands/Integration/SearchCommandIntegrationTests.cs
@@ -29,10 +29,8 @@ public class SearchCommandIntegrationTests
 
     private readonly ILogger<SearchCommand> _logger;
 
-    public SearchCommandIntegrationTests(ITestOutputHelper outputHelper)
-    {
+    public SearchCommandIntegrationTests(ITestOutputHelper outputHelper) =>
         _logger = XUnitLogger.CreateLogger<SearchCommand>(outputHelper);
-    }
 
     private static string? ApiKey => Configuration["bottomly_brave_api_key"];
 
@@ -47,11 +45,6 @@ private SearchCommand CreateCommand()
         }), _logger, factory);
     }
 
-    private sealed class DefaultHttpClientFactory : IHttpClientFactory
-    {
-        public HttpClient CreateClient(string name) => new();
-    }
-
     [Fact]
     public async Task ExecuteAsync_EmptyInput_ReturnsEmptySearchTermErrorResult()
     {
@@ -96,4 +89,9 @@ public async Task ExecuteAsync_KnownSearchTerm_ReturnsRelevantResult()
         var searchResult = (SearchResult)result;
         searchResult.Link.ShouldContain("wikipedia");
     }
+
+    private sealed class DefaultHttpClientFactory : IHttpClientFactory
+    {
+        public HttpClient CreateClient(string name) => new();
+    }
 }
\ No newline at end of file
diff --git a/Bottomly.Tests/Commands/Integration/WikipediaSearchCommandIntegrationTests.cs b/Bottomly.Tests/Commands/Integration/WikipediaSearchCommandIntegrationTests.cs
index 46ac021..ca1089c 100644
--- a/Bottomly.Tests/Commands/Integration/WikipediaSearchCommandIntegrationTests.cs
+++ b/Bottomly.Tests/Commands/Integration/WikipediaSearchCommandIntegrationTests.cs
@@ -1,4 +1,5 @@
 using Bottomly.Commands;
+using Microsoft.Extensions.Logging.Abstractions;
 using Moq;
 using Shouldly;
 
@@ -19,25 +20,25 @@ public WikipediaSearchCommandIntegrationTests()
         var factory = new Mock<IHttpClientFactory>();
         factory.Setup(f => f.CreateClient(It.IsAny<string>())).Returns(client);
 
-        _sut = new WikipediaSearchCommand(factory.Object);
+        _sut = new WikipediaSearchCommand(factory.Object, NullLogger<WikipediaSearchCommand>.Instance);
     }
 
     [Fact]
-    public async Task ExecuteAsync_EmptyInput_ReturnsNull()
+    public async Task ExecuteAsync_EmptyInput_ReturnsEmptyInputResult()
     {
         var result = await _sut.ExecuteAsync("");
 
-        result.ShouldBeNull();
+        result.ShouldBeOfType<WikipediaEmptyInputResult>();
     }
 
     [Fact]
-    public async Task ExecuteAsync_KnownSearchTerm_ReturnsResultWithWikipediaLink()
+    public async Task ExecuteAsync_KnownSearchTerm_ReturnsSuccessResultWithWikipediaLink()
     {
         var result = await _sut.ExecuteAsync("Albert Einstein");
 
-        result.ShouldNotBeNull();
-        result!.Text.ShouldNotBeNullOrEmpty();
-        result.Link.ShouldStartWith("https://en.wikipedia.org/wiki/");
+        var success = result.ShouldBeOfType<WikipediaSuccessResult>();
+        success.Text.ShouldNotBeNullOrEmpty();
+        success.Link.ShouldStartWith("https://en.wikipedia.org/wiki/");
     }
 
     [Fact]
@@ -45,15 +46,15 @@ public async Task ExecuteAsync_KnownSearchTerm_ReturnsExpectedTitle()
     {
         var result = await _sut.ExecuteAsync("London");
 
-        result.ShouldNotBeNull();
-        result!.Text.ShouldBe("London");
+        var success = result.ShouldBeOfType<WikipediaSuccessResult>();
+        success.Text.ShouldBe("London");
     }
 
     [Fact]
-    public async Task ExecuteAsync_GibberishInput_ReturnsNull()
+    public async Task ExecuteAsync_GibberishInput_ReturnsNotFoundResult()
     {
         var result = await _sut.ExecuteAsync("xyzzy_no_such_article_12345");
 
-        result.ShouldBeNull();
+        result.ShouldBeOfType<WikipediaNotFoundResult>();
     }
 }
\ No newline at end of file
diff --git a/Bottomly.Tests/Commands/RegSearchCommandTests.cs b/Bottomly.Tests/Commands/RegSearchCommandTests.cs
index 8f1c363..1305176 100644
--- a/Bottomly.Tests/Commands/RegSearchCommandTests.cs
+++ b/Bottomly.Tests/Commands/RegSearchCommandTests.cs
@@ -41,14 +41,14 @@ public async Task ExecuteAsync_SpecialChars_ReturnsSpecialCharsMessage()
     public async Task ExecuteAsync_ValidReg_ParsesHtmlResponse()
     {
         const string html = """
-            <html><body>
-                <input id="VehicleColour" value="Blue" />
-                <input id="RegistrationYear" value="2019" />
-                <input id="VehicleMake" value="FORD" />
-                <input id="VehicleModel" value="FOCUS" />
-                <img id="searchResultCarImage" src="/images/car.jpg" />
-            </body></html>
-            """;
+                            <html><body>
+                                <input id="VehicleColour" value="Blue" />
+                                <input id="RegistrationYear" value="2019" />
+                                <input id="VehicleMake" value="FORD" />
+                                <input id="VehicleModel" value="FOCUS" />
+                                <img id="searchResultCarImage" src="/images/car.jpg" />
+                            </body></html>
+                            """;
 
         var factory = TestHelpers.CreateHttpClientFactory(html);
         var command = new RegSearchCommand(factory);
@@ -81,11 +81,11 @@ public async Task ExecuteAsync_HtmlWithError_ReturnsErrorText()
     {
         // An element with an empty value causes make[0] to throw, which triggers the catch block
         const string html = """
-            <html><body>
-                <input id="VehicleMake" value="" />
-                <div class="ErrorMessage"><h3>Vehicle not found</h3></div>
-            </body></html>
-            """;
+                            <html><body>
+                                <input id="VehicleMake" value="" />
+                                <div class="ErrorMessage"><h3>Vehicle not found</h3></div>
+                            </body></html>
+                            """;
 
         var factory = TestHelpers.CreateHttpClientFactory(html);
         var command = new RegSearchCommand(factory);
diff --git a/Bottomly.Tests/Commands/SearchCommandTests.cs b/Bottomly.Tests/Commands/SearchCommandTests.cs
index f28a1b4..fa52348 100644
--- a/Bottomly.Tests/Commands/SearchCommandTests.cs
+++ b/Bottomly.Tests/Commands/SearchCommandTests.cs
@@ -1,10 +1,10 @@
+using System.Net;
 using Bottomly.Commands.Search;
 using Bottomly.Configuration;
 using Bottomly.Tests.Helpers;
 using Microsoft.Extensions.Logging.Abstractions;
 using Microsoft.Extensions.Options;
 using Shouldly;
-using System.Net;
 
 namespace Bottomly.Tests.Commands;
 
@@ -47,13 +47,13 @@ public async Task ExecuteAsync_WhitespaceInput_ReturnsEmptySearchTermErrorResult
     public async Task ExecuteAsync_ApiReturnsResults_ReturnsSearchResultWithTitleAndLink()
     {
         const string json = """
-            {
-              "type": "search",
-              "web": {
-                "results": [{ "title": "DotNet", "url": "https://dotnet.microsoft.com" }]
-              }
-            }
-            """;
+                            {
+                              "type": "search",
+                              "web": {
+                                "results": [{ "title": "DotNet", "url": "https://dotnet.microsoft.com" }]
+                              }
+                            }
+                            """;
 
         var result = await CreateCommand(json).ExecuteAsync("dotnet");
 
diff --git a/Bottomly.Tests/Commands/UrbanSearchCommandTests.cs b/Bottomly.Tests/Commands/UrbanSearchCommandTests.cs
index 0d1a09e..69591cf 100644
--- a/Bottomly.Tests/Commands/UrbanSearchCommandTests.cs
+++ b/Bottomly.Tests/Commands/UrbanSearchCommandTests.cs
@@ -1,5 +1,6 @@
 using Bottomly.Commands;
 using Bottomly.Tests.Helpers;
+using Microsoft.Extensions.Logging.Abstractions;
 using Moq;
 using Shouldly;
 
@@ -8,35 +9,36 @@ namespace Bottomly.Tests.Commands;
 public class UrbanSearchCommandTests
 {
     [Fact]
-    public async Task ExecuteAsync_EmptyInput_ReturnsNull()
+    public async Task ExecuteAsync_EmptyInput_ReturnsEmptyInputResult()
     {
         var mockFactory = new Mock<IHttpClientFactory>();
-        var command = new UrbanSearchCommand(mockFactory.Object);
+        var command = new UrbanSearchCommand(mockFactory.Object, NullLogger<UrbanSearchCommand>.Instance);
 
         var result = await command.ExecuteAsync("");
 
-        result.ShouldBeNull();
+        result.ShouldBeOfType<UrbanEmptyInputResult>();
     }
 
     [Fact]
-    public async Task ExecuteAsync_WithResults_ReturnsDefinition()
+    public async Task ExecuteAsync_WithResults_ReturnsSuccessResult()
     {
         const string json = """{"list":[{"definition":"A domestic animal that owns you."}]}""";
-        var command = new UrbanSearchCommand(TestHelpers.CreateHttpClientFactory(json));
+        var command = new UrbanSearchCommand(TestHelpers.CreateHttpClientFactory(json), NullLogger<UrbanSearchCommand>.Instance);
 
         var result = await command.ExecuteAsync("cat");
 
-        result.ShouldBe("A domestic animal that owns you.");
+        var success = result.ShouldBeOfType<UrbanSuccessResult>();
+        success.Definition.ShouldBe("A domestic animal that owns you.");
     }
 
     [Fact]
-    public async Task ExecuteAsync_NoResults_ReturnsNull()
+    public async Task ExecuteAsync_NoResults_ReturnsNotFoundResult()
     {
         const string json = """{"list":[]}""";
-        var command = new UrbanSearchCommand(TestHelpers.CreateHttpClientFactory(json));
+        var command = new UrbanSearchCommand(TestHelpers.CreateHttpClientFactory(json), NullLogger<UrbanSearchCommand>.Instance);
 
         var result = await command.ExecuteAsync("xyznotaword");
 
-        result.ShouldBeNull();
+        result.ShouldBeOfType<UrbanNotFoundResult>();
     }
 }
\ No newline at end of file
diff --git a/Bottomly.Tests/Commands/WikipediaSearchCommandTests.cs b/Bottomly.Tests/Commands/WikipediaSearchCommandTests.cs
index 95f50dd..f833510 100644
--- a/Bottomly.Tests/Commands/WikipediaSearchCommandTests.cs
+++ b/Bottomly.Tests/Commands/WikipediaSearchCommandTests.cs
@@ -1,5 +1,6 @@
 using Bottomly.Commands;
 using Bottomly.Tests.Helpers;
+using Microsoft.Extensions.Logging.Abstractions;
 using Moq;
 using Shouldly;
 
@@ -8,37 +9,38 @@ namespace Bottomly.Tests.Commands;
 public class WikipediaSearchCommandTests
 {
     [Fact]
-    public async Task ExecuteAsync_EmptyInput_ReturnsNull()
+    public async Task ExecuteAsync_EmptyInput_ReturnsEmptyInputResult()
     {
         var mockFactory = new Mock<IHttpClientFactory>();
-        var command = new WikipediaSearchCommand(mockFactory.Object);
+        var command = new WikipediaSearchCommand(mockFactory.Object, NullLogger<WikipediaSearchCommand>.Instance);
 
         var result = await command.ExecuteAsync("");
 
-        result.ShouldBeNull();
+        result.ShouldBeOfType<WikipediaEmptyInputResult>();
     }
 
     [Fact]
-    public async Task ExecuteAsync_WithResults_ReturnsTitleAndLink()
+    public async Task ExecuteAsync_WithResults_ReturnsSuccessResult()
     {
-        const string json = """["cat",["Cat","Cat (disambiguation)"],["",""],["https://en.wikipedia.org/wiki/Cat","https://en.wikipedia.org/wiki/Cat_(disambiguation)"]]""";
-        var command = new WikipediaSearchCommand(TestHelpers.CreateHttpClientFactory(json));
+        const string json =
+            """["cat",["Cat","Cat (disambiguation)"],["",""],["https://en.wikipedia.org/wiki/Cat","https://en.wikipedia.org/wiki/Cat_(disambiguation)"]]""";
+        var command = new WikipediaSearchCommand(TestHelpers.CreateHttpClientFactory(json), NullLogger<WikipediaSearchCommand>.Instance);
 
         var result = await command.ExecuteAsync("cat");
 
-        result.ShouldNotBeNull();
-        result!.Text.ShouldBe("Cat");
-        result.Link.ShouldBe("https://en.wikipedia.org/wiki/Cat");
+        var success = result.ShouldBeOfType<WikipediaSuccessResult>();
+        success.Text.ShouldBe("Cat");
+        success.Link.ShouldBe("https://en.wikipedia.org/wiki/Cat");
     }
 
     [Fact]
-    public async Task ExecuteAsync_NoResults_ReturnsNull()
+    public async Task ExecuteAsync_NoResults_ReturnsNotFoundResult()
     {
         const string json = """["unknownxyz",[],[],[]]""";
-        var command = new WikipediaSearchCommand(TestHelpers.CreateHttpClientFactory(json));
+        var command = new WikipediaSearchCommand(TestHelpers.CreateHttpClientFactory(json), NullLogger<WikipediaSearchCommand>.Instance);
 
         var result = await command.ExecuteAsync("unknownxyz");
 
-        result.ShouldBeNull();
+        result.ShouldBeOfType<WikipediaNotFoundResult>();
     }
 }
\ No newline at end of file
diff --git a/Bottomly.Tests/Helpers/TestHelpers.cs b/Bottomly.Tests/Helpers/TestHelpers.cs
index d562e7a..1e1e944 100644
--- a/Bottomly.Tests/Helpers/TestHelpers.cs
+++ b/Bottomly.Tests/Helpers/TestHelpers.cs
@@ -14,8 +14,8 @@ public static IOptions<BottomlyOptions> CreateOptions(string prefix = TestPrefix
         Options.Create(new BottomlyOptions { Prefix = prefix });
 
     /// <summary>
-    /// Creates a <see cref="System.Net.Http.IHttpClientFactory"/> that returns a fake HTTP response,
-    /// allowing unit tests to exercise HTTP-based commands without hitting real external APIs.
+    ///     Creates a <see cref="System.Net.Http.IHttpClientFactory" /> that returns a fake HTTP response,
+    ///     allowing unit tests to exercise HTTP-based commands without hitting real external APIs.
     /// </summary>
     public static MsHttpClientFactory CreateHttpClientFactory(string responseContent,
         HttpStatusCode statusCode = HttpStatusCode.OK)
@@ -26,7 +26,6 @@ public static MsHttpClientFactory CreateHttpClientFactory(string responseContent
         factory.Setup(f => f.CreateClient(It.IsAny<string>())).Returns(client);
         return factory.Object;
     }
-
 }
 
 internal class FakeHttpMessageHandler(string content, HttpStatusCode statusCode = HttpStatusCode.OK)
diff --git a/Bottomly.Tests/Infrastructure/MongoDbFixture.cs b/Bottomly.Tests/Infrastructure/MongoDbFixture.cs
index 2778318..ff38b40 100644
--- a/Bottomly.Tests/Infrastructure/MongoDbFixture.cs
+++ b/Bottomly.Tests/Infrastructure/MongoDbFixture.cs
@@ -4,8 +4,8 @@
 namespace Bottomly.Tests.Infrastructure;
 
 /// <summary>
-/// Shared xUnit fixture that starts a single MongoDB container for the entire test collection.
-/// Each test class should call <see cref="GetDatabase"/> with a unique name to ensure isolation.
+///     Shared xUnit fixture that starts a single MongoDB container for the entire test collection.
+///     Each test class should call <see cref="GetDatabase" /> with a unique name to ensure isolation.
 /// </summary>
 public sealed class MongoDbFixture : IAsyncLifetime
 {
@@ -14,8 +14,6 @@ public sealed class MongoDbFixture : IAsyncLifetime
 
     public IMongoClient Client { get; private set; } = null!;
 
-    public IMongoDatabase GetDatabase(string name) => Client.GetDatabase(name);
-
     public async Task InitializeAsync()
     {
         await _container.StartAsync();
@@ -23,4 +21,6 @@ public async Task InitializeAsync()
     }
 
     public async Task DisposeAsync() => await _container.DisposeAsync();
+
+    public IMongoDatabase GetDatabase(string name) => Client.GetDatabase(name);
 }
\ No newline at end of file
diff --git a/Bottomly.Tests/LlmBot/LlmClientTests.cs b/Bottomly.Tests/LlmBot/LlmClientTests.cs
index daa613a..530c124 100644
--- a/Bottomly.Tests/LlmBot/LlmClientTests.cs
+++ b/Bottomly.Tests/LlmBot/LlmClientTests.cs
@@ -8,13 +8,10 @@ namespace Bottomly.Tests.LlmBot;
 
 public class LlmClientTests
 {
-    private readonly Mock<IChatClient> _mockChatClient = new();
     private readonly LlmClient _broker;
+    private readonly Mock<IChatClient> _mockChatClient = new();
 
-    public LlmClientTests()
-    {
-        _broker = new LlmClient(_mockChatClient.Object, NullLogger<LlmClient>.Instance);
-    }
+    public LlmClientTests() => _broker = new LlmClient(_mockChatClient.Object, NullLogger<LlmClient>.Instance);
 
     [Fact]
     public async Task Respond_SuccessfulResponse_ReturnsLlmMessageResponse()
diff --git a/Bottomly.Tests/Repositories/Integration/FeatureFlagRepositoryIntegrationTests.cs b/Bottomly.Tests/Repositories/Integration/FeatureFlagRepositoryIntegrationTests.cs
index 9cb47a4..fdb0d89 100644
--- a/Bottomly.Tests/Repositories/Integration/FeatureFlagRepositoryIntegrationTests.cs
+++ b/Bottomly.Tests/Repositories/Integration/FeatureFlagRepositoryIntegrationTests.cs
@@ -127,4 +127,4 @@ public async Task SetAsync_DifferentFlagIds_AreStoredIndependently()
         (await _sut.GetAsync("EnableLlm")).ShouldBeTrue();
         (await _sut.GetAsync("AnotherFlag")).ShouldBeFalse();
     }
-}
+}
\ No newline at end of file
diff --git a/Bottomly.Tests/Repositories/Integration/KarmaRepositoryIntegrationTests.cs b/Bottomly.Tests/Repositories/Integration/KarmaRepositoryIntegrationTests.cs
index dda33d4..3075c22 100644
--- a/Bottomly.Tests/Repositories/Integration/KarmaRepositoryIntegrationTests.cs
+++ b/Bottomly.Tests/Repositories/Integration/KarmaRepositoryIntegrationTests.cs
@@ -91,7 +91,7 @@ public async Task GetKarmaReasonsAsync_SeparatesReasonedFromReasonless()
         result.Reasonless.ShouldBe(1);
         result.Reasoned.Count.ShouldBe(2);
         result.Reasoned.Select(k => k.Reason).ShouldBe(
-            ["fixed the build", "great docs"], ignoreOrder: true);
+            ["fixed the build", "great docs"], true);
     }
 
     [Fact]
@@ -122,12 +122,12 @@ public async Task GetLeaderBoardAsync_ReturnsCorrectOrderAndSize()
     {
         // net_karma: PozzyPoz → –1, NeggyNeg → +1
         // Leader board is sorted Descending by net_karma
-        await AddKarmaMultiple("leader-a", KarmaType.NeggyNeg, 5);  // net +5
-        await AddKarmaMultiple("leader-b", KarmaType.NeggyNeg, 3);  // net +3
-        await AddKarmaMultiple("leader-c", KarmaType.NeggyNeg, 1);  // net +1
+        await AddKarmaMultiple("leader-a", KarmaType.NeggyNeg, 5); // net +5
+        await AddKarmaMultiple("leader-b", KarmaType.NeggyNeg, 3); // net +3
+        await AddKarmaMultiple("leader-c", KarmaType.NeggyNeg, 1); // net +1
         await AddKarmaMultiple("leader-d", KarmaType.PozzyPoz, 2); // net –2 (should not appear in top 3)
 
-        var board = await _sut.GetLeaderBoardAsync(3);
+        var board = await _sut.GetLeaderBoardAsync();
 
         board.Count.ShouldBe(3);
         board[0].Username.ShouldBe("leader-a");
@@ -142,12 +142,12 @@ public async Task GetLeaderBoardAsync_ReturnsCorrectOrderAndSize()
     public async Task GetLoserBoardAsync_ReturnsCorrectOrderAndSize()
     {
         // Loser board is sorted Ascending by net_karma
-        await AddKarmaMultiple("loser-a", KarmaType.PozzyPoz, 5);  // net –5
-        await AddKarmaMultiple("loser-b", KarmaType.PozzyPoz, 3);  // net –3
-        await AddKarmaMultiple("loser-c", KarmaType.PozzyPoz, 1);  // net –1
-        await AddKarmaMultiple("loser-d", KarmaType.NeggyNeg, 2);  // net +2 (should not appear in top 3)
+        await AddKarmaMultiple("loser-a", KarmaType.PozzyPoz, 5); // net –5
+        await AddKarmaMultiple("loser-b", KarmaType.PozzyPoz, 3); // net –3
+        await AddKarmaMultiple("loser-c", KarmaType.PozzyPoz, 1); // net –1
+        await AddKarmaMultiple("loser-d", KarmaType.NeggyNeg, 2); // net +2 (should not appear in top 3)
 
-        var board = await _sut.GetLoserBoardAsync(3);
+        var board = await _sut.GetLoserBoardAsync();
 
         board.Count.ShouldBe(3);
         board[0].Username.ShouldBe("loser-a");
diff --git a/Bottomly.Tests/Repositories/Integration/MemberRepositoryIntegrationTests.cs b/Bottomly.Tests/Repositories/Integration/MemberRepositoryIntegrationTests.cs
index 2c9e04a..2a8740f 100644
--- a/Bottomly.Tests/Repositories/Integration/MemberRepositoryIntegrationTests.cs
+++ b/Bottomly.Tests/Repositories/Integration/MemberRepositoryIntegrationTests.cs
@@ -74,7 +74,7 @@ await _sut.AddAsync([
         var result = await _sut.GetBySlackIdsAsync(["U001", "U003"]);
 
         result.Count.ShouldBe(2);
-        result.Select(m => m.Username).ShouldBe(["alice", "carol"], ignoreOrder: true);
+        result.Select(m => m.Username).ShouldBe(["alice", "carol"], true);
     }
 
     [Fact]
@@ -145,10 +145,8 @@ await _sut.AddAsync(new Member
     }
 
     [Fact]
-    public async Task UpdateInfoAsync_WhenUsernameDoesNotExist_DoesNotThrow()
-    {
+    public async Task UpdateInfoAsync_WhenUsernameDoesNotExist_DoesNotThrow() =>
         // Should silently no-op (UpdateOne with no match)
         await Should.NotThrowAsync(() =>
             _sut.UpdateInfoAsync("ghost", "Ghost", Gender.Unknown, SassLevel.None, ""));
-    }
 }
\ No newline at end of file
diff --git a/Bottomly.Tests/Repositories/Unit/CachingMemberRepositoryTests.cs b/Bottomly.Tests/Repositories/Unit/CachingMemberRepositoryTests.cs
index f92aad7..f39d18e 100644
--- a/Bottomly.Tests/Repositories/Unit/CachingMemberRepositoryTests.cs
+++ b/Bottomly.Tests/Repositories/Unit/CachingMemberRepositoryTests.cs
@@ -9,14 +9,11 @@ namespace Bottomly.Tests.Repositories.Unit;
 
 public class CachingMemberRepositoryTests
 {
-    private readonly Mock<IMemberRepository> _mockInner = new();
     private readonly IMemoryCache _cache = new MemoryCache(Options.Create(new MemoryCacheOptions()));
+    private readonly Mock<IMemberRepository> _mockInner = new();
     private readonly CachingMemberRepository _repo;
 
-    public CachingMemberRepositoryTests()
-    {
-        _repo = new CachingMemberRepository(_mockInner.Object, _cache);
-    }
+    public CachingMemberRepositoryTests() => _repo = new CachingMemberRepository(_mockInner.Object, _cache);
 
     [Fact]
     public async Task GetBySlackIdAsync_CacheMiss_CallsInnerAndCachesResult()
@@ -73,7 +70,7 @@ public async Task GetBySlackIdAsync_AfterGetByUsernameAsync_DoesNotCallInner()
         _mockInner.Setup(r => r.GetByUsernameAsync("alice")).ReturnsAsync(member);
 
         await _repo.GetByUsernameAsync("alice"); // Caches by both keys
-        await _repo.GetBySlackIdAsync("U1");     // Should hit cache (cross-key)
+        await _repo.GetBySlackIdAsync("U1"); // Should hit cache (cross-key)
 
         _mockInner.Verify(r => r.GetBySlackIdAsync("U1"), Times.Never);
     }
@@ -148,7 +145,9 @@ public async Task AddAsync_SingleMember_CachesMember()
     public async Task UpdateInfoAsync_UpdatesCacheWithFreshData()
     {
         var updated = new Member { SlackId = "U1", Username = "alice", FullName = "Alice Smith" };
-        _mockInner.Setup(r => r.UpdateInfoAsync("alice", "Alice Smith", It.IsAny<Gender>(), It.IsAny<SassLevel>(), It.IsAny<string>()))
+        _mockInner.Setup(r =>
+                r.UpdateInfoAsync("alice", "Alice Smith", It.IsAny<Gender>(), It.IsAny<SassLevel>(),
+                    It.IsAny<string>()))
             .Returns(Task.CompletedTask);
         _mockInner.Setup(r => r.GetByUsernameAsync("alice")).ReturnsAsync(updated);
 
@@ -158,4 +157,4 @@ public async Task UpdateInfoAsync_UpdatesCacheWithFreshData()
         result!.FullName.ShouldBe("Alice Smith");
         _mockInner.Verify(r => r.GetByUsernameAsync("alice"), Times.Once); // Called once during UpdateInfoAsync
     }
-}
+}
\ No newline at end of file
diff --git a/Bottomly.Tests/Slack/EventHandlers/GiphyHandlerTests.cs b/Bottomly.Tests/Slack/EventHandlers/GiphyHandlerTests.cs
index 421f76d..2ce89fe 100644
--- a/Bottomly.Tests/Slack/EventHandlers/GiphyHandlerTests.cs
+++ b/Bottomly.Tests/Slack/EventHandlers/GiphyHandlerTests.cs
@@ -52,7 +52,8 @@ public async Task HandleAsync_ValidEvent_WithResult_SendsImageBlock()
 
         IReadOnlyList<Block>? capturedBlocks = null;
         _mockBroker
-            .Setup(b => b.SendBlocksMessageAsync(It.IsAny<IReadOnlyList<Block>>(), It.IsAny<string>(), It.IsAny<string?>(), It.IsAny<string?>()))
+            .Setup(b => b.SendBlocksMessageAsync(It.IsAny<IReadOnlyList<Block>>(), It.IsAny<string>(),
+                It.IsAny<string?>(), It.IsAny<string?>()))
             .Callback<IReadOnlyList<Block>, string, string?, string?>((blocks, _, _, _) => capturedBlocks = blocks)
             .Returns(Task.CompletedTask);
 
diff --git a/Bottomly.Tests/Slack/EventHandlers/ImageSearchHandlerTests.cs b/Bottomly.Tests/Slack/EventHandlers/ImageSearchHandlerTests.cs
index e1ef848..cc5f5a3 100644
--- a/Bottomly.Tests/Slack/EventHandlers/ImageSearchHandlerTests.cs
+++ b/Bottomly.Tests/Slack/EventHandlers/ImageSearchHandlerTests.cs
@@ -25,22 +25,15 @@ public ImageSearchHandlerTests()
             NullLogger<ImageSearchHandler>.Instance);
     }
 
-    private static MessageEvent CreateMessage(string text)
-    {
-        return new MessageEvent { Text = text, User = "U1", Channel = "C1", Ts = "ts1" };
-    }
+    private static MessageEvent CreateMessage(string text) =>
+        new() { Text = text, User = "U1", Channel = "C1", Ts = "ts1" };
 
     [Fact]
-    public void CanHandle_ValidEvent_ReturnsTrue()
-    {
-        _handler.CanHandle(CreateMessage("_gi cats")).ShouldBeTrue();
-    }
+    public void CanHandle_ValidEvent_ReturnsTrue() => _handler.CanHandle(CreateMessage("_gi cats")).ShouldBeTrue();
 
     [Fact]
-    public void CanHandle_InvalidEvent_ReturnsFalse()
-    {
+    public void CanHandle_InvalidEvent_ReturnsFalse() =>
         _handler.CanHandle(CreateMessage("no prefix here")).ShouldBeFalse();
-    }
 
     [Fact]
     public async Task HandleAsync_ValidEvent_CallsCommandWithQuery()
@@ -60,7 +53,8 @@ public async Task HandleAsync_ValidEvent_WithResult_SendsImageBlock()
 
         IReadOnlyList<Block>? capturedBlocks = null;
         _mockBroker
-            .Setup(b => b.SendBlocksMessageAsync(It.IsAny<IReadOnlyList<Block>>(), It.IsAny<string>(), It.IsAny<string?>(), It.IsAny<string?>()))
+            .Setup(b => b.SendBlocksMessageAsync(It.IsAny<IReadOnlyList<Block>>(), It.IsAny<string>(),
+                It.IsAny<string?>(), It.IsAny<string?>()))
             .Callback<IReadOnlyList<Block>, string, string?, string?>((blocks, _, _, _) => capturedBlocks = blocks)
             .Returns(Task.CompletedTask);
 
diff --git a/Bottomly.Tests/Slack/EventHandlers/KarmaEventHandlers/DecrementMessageKarmaEventHandlerTests.cs b/Bottomly.Tests/Slack/EventHandlers/KarmaEventHandlers/DecrementMessageKarmaEventHandlerTests.cs
index 439869b..1a5dfb6 100644
--- a/Bottomly.Tests/Slack/EventHandlers/KarmaEventHandlers/DecrementMessageKarmaEventHandlerTests.cs
+++ b/Bottomly.Tests/Slack/EventHandlers/KarmaEventHandlers/DecrementMessageKarmaEventHandlerTests.cs
@@ -21,7 +21,7 @@ public class DecrementMessageKarmaEventHandlerTests
     public DecrementMessageKarmaEventHandlerTests()
     {
         var options = TestHelpers.CreateOptions();
-        var command = new AddKarmaCommand(_mockKarmaRepo.Object);
+        var command = new AddKarmaCommand(_mockKarmaRepo.Object, NullLogger<AddKarmaCommand>.Instance);
         var parser = new SlackParser(_mockMemberRepo.Object);
         _handler = new DecrementMessageKarmaEventHandler(command, parser, _mockMemberRepo.Object, _mockBroker.Object,
             options,
diff --git a/Bottomly.Tests/Slack/EventHandlers/KarmaEventHandlers/IncrementMessageKarmaEventHandlerTests.cs b/Bottomly.Tests/Slack/EventHandlers/KarmaEventHandlers/IncrementMessageKarmaEventHandlerTests.cs
index 7e99892..5d429b8 100644
--- a/Bottomly.Tests/Slack/EventHandlers/KarmaEventHandlers/IncrementMessageKarmaEventHandlerTests.cs
+++ b/Bottomly.Tests/Slack/EventHandlers/KarmaEventHandlers/IncrementMessageKarmaEventHandlerTests.cs
@@ -21,7 +21,7 @@ public class IncrementMessageKarmaEventHandlerTests
     public IncrementMessageKarmaEventHandlerTests()
     {
         var options = TestHelpers.CreateOptions();
-        var command = new AddKarmaCommand(_mockKarmaRepo.Object);
+        var command = new AddKarmaCommand(_mockKarmaRepo.Object, NullLogger<AddKarmaCommand>.Instance);
         var parser = new SlackParser(_mockMemberRepo.Object);
         _handler = new IncrementMessageKarmaEventHandler(command, parser, _mockMemberRepo.Object, _mockBroker.Object,
             options,
diff --git a/Bottomly.Tests/Slack/EventHandlers/KarmaEventHandlers/KarmaHandlerCommandParsingTests.cs b/Bottomly.Tests/Slack/EventHandlers/KarmaEventHandlers/KarmaHandlerCommandParsingTests.cs
index 120ca15..0821c67 100644
--- a/Bottomly.Tests/Slack/EventHandlers/KarmaEventHandlers/KarmaHandlerCommandParsingTests.cs
+++ b/Bottomly.Tests/Slack/EventHandlers/KarmaEventHandlers/KarmaHandlerCommandParsingTests.cs
@@ -20,7 +20,7 @@ public class KarmaHandlerCommandParsingTests
     public KarmaHandlerCommandParsingTests()
     {
         var options = TestHelpers.CreateOptions();
-        var command = new AddKarmaCommand(_mockKarmaRepo.Object);
+        var command = new AddKarmaCommand(_mockKarmaRepo.Object, NullLogger<AddKarmaCommand>.Instance);
         var parser = new SlackParser(_mockMemberRepo.Object);
         _handler = new IncrementMessageKarmaEventHandler(command, parser, _mockMemberRepo.Object, _mockBroker.Object,
             options,
diff --git a/Bottomly.Tests/Slack/EventHandlers/RegHandlerTests.cs b/Bottomly.Tests/Slack/EventHandlers/RegHandlerTests.cs
index 9b6050b..0709b92 100644
--- a/Bottomly.Tests/Slack/EventHandlers/RegHandlerTests.cs
+++ b/Bottomly.Tests/Slack/EventHandlers/RegHandlerTests.cs
@@ -1,5 +1,4 @@
 using Bottomly.Commands;
-using Bottomly.Configuration;
 using Bottomly.Slack;
 using Bottomly.Slack.MessageEventHandlers;
 using Bottomly.Tests.Helpers;
diff --git a/Bottomly.Tests/Slack/EventHandlers/ReleaseHandlerTests.cs b/Bottomly.Tests/Slack/EventHandlers/ReleaseHandlerTests.cs
index e63c524..4883586 100644
--- a/Bottomly.Tests/Slack/EventHandlers/ReleaseHandlerTests.cs
+++ b/Bottomly.Tests/Slack/EventHandlers/ReleaseHandlerTests.cs
@@ -38,7 +38,7 @@ private static MessageEvent CreateMessage(string text) =>
     [Fact]
     public async Task HandleAsync_WithResult_SendsResult()
     {
-        _mockCommand.Setup(c => c.ExecuteAsync()).ReturnsAsync("Latest Release: *v1.0* v1.0");
+        _mockCommand.Setup(c => c.ExecuteAsync()).ReturnsAsync(new ReleaseSuccessResult("Latest Release: *v1.0* v1.0"));
 
         await _handler.HandleAsync(CreateMessage("_release"));
 
@@ -46,9 +46,9 @@ public async Task HandleAsync_WithResult_SendsResult()
     }
 
     [Fact]
-    public async Task HandleAsync_NullResult_SendsUnableMessage()
+    public async Task HandleAsync_ErrorResult_SendsUnableMessage()
     {
-        _mockCommand.Setup(c => c.ExecuteAsync()).ReturnsAsync((string?)null);
+        _mockCommand.Setup(c => c.ExecuteAsync()).ReturnsAsync(new ReleaseErrorResult());
 
         await _handler.HandleAsync(CreateMessage("_release"));
 
diff --git a/Bottomly.Tests/Slack/EventHandlers/SearchHandlerTests.cs b/Bottomly.Tests/Slack/EventHandlers/SearchHandlerTests.cs
index eaf358b..09a485b 100644
--- a/Bottomly.Tests/Slack/EventHandlers/SearchHandlerTests.cs
+++ b/Bottomly.Tests/Slack/EventHandlers/SearchHandlerTests.cs
@@ -24,22 +24,16 @@ public SearchHandlerTests()
             NullLogger<SearchHandler>.Instance);
     }
 
-    private static MessageEvent CreateMessage(string text)
-    {
-        return new MessageEvent { Text = text, User = "U1", Channel = "C1", Ts = "ts1" };
-    }
+    private static MessageEvent CreateMessage(string text) =>
+        new() { Text = text, User = "U1", Channel = "C1", Ts = "ts1" };
 
     [Fact]
-    public void CanHandle_ValidEvent_ReturnsTrue()
-    {
+    public void CanHandle_ValidEvent_ReturnsTrue() =>
         _handler.CanHandle(CreateMessage("_g a valid google command")).ShouldBeTrue();
-    }
 
     [Fact]
-    public void CanHandle_InvalidEvent_ReturnsFalse()
-    {
+    public void CanHandle_InvalidEvent_ReturnsFalse() =>
         _handler.CanHandle(CreateMessage("no prefix here")).ShouldBeFalse();
-    }
 
     [Fact]
     public async Task HandleAsync_ValidEvent_CallsCommandWithQuery()
diff --git a/Bottomly.Tests/Slack/EventHandlers/UrbanHandlerTests.cs b/Bottomly.Tests/Slack/EventHandlers/UrbanHandlerTests.cs
index d9987ba..e6bdfac 100644
--- a/Bottomly.Tests/Slack/EventHandlers/UrbanHandlerTests.cs
+++ b/Bottomly.Tests/Slack/EventHandlers/UrbanHandlerTests.cs
@@ -19,7 +19,7 @@ public UrbanHandlerTests()
     {
         var options = TestHelpers.CreateOptions();
         var mockFactory = new Mock<IHttpClientFactory>();
-        _mockCommand = new Mock<UrbanSearchCommand>(mockFactory.Object);
+        _mockCommand = new Mock<UrbanSearchCommand>(mockFactory.Object, NullLogger<UrbanSearchCommand>.Instance);
         _handler = new UrbanHandler(_mockCommand.Object, _mockBroker.Object, options,
             NullLogger<UrbanHandler>.Instance);
     }
@@ -36,7 +36,7 @@ private static MessageEvent CreateMessage(string text) =>
     [Fact]
     public async Task HandleAsync_ValidEvent_CallsCommandWithTerm()
     {
-        _mockCommand.Setup(c => c.ExecuteAsync("hello")).ReturnsAsync((string?)null);
+        _mockCommand.Setup(c => c.ExecuteAsync("hello")).ReturnsAsync(new UrbanNotFoundResult());
 
         await _handler.HandleAsync(CreateMessage("_ud hello"));
 
@@ -46,7 +46,7 @@ public async Task HandleAsync_ValidEvent_CallsCommandWithTerm()
     [Fact]
     public async Task HandleAsync_ValidEvent_WithResult_SendsReplyResponse()
     {
-        _mockCommand.Setup(c => c.ExecuteAsync("hello")).ReturnsAsync("a greeting");
+        _mockCommand.Setup(c => c.ExecuteAsync("hello")).ReturnsAsync(new UrbanSuccessResult("a greeting"));
         var message = CreateMessage("_ud hello");
 
         await _handler.HandleAsync(message);
@@ -56,9 +56,9 @@ public async Task HandleAsync_ValidEvent_WithResult_SendsReplyResponse()
     }
 
     [Fact]
-    public async Task HandleAsync_ValidEvent_NullResult_SendsExerciseMessage()
+    public async Task HandleAsync_ValidEvent_NotFoundResult_SendsExerciseMessage()
     {
-        _mockCommand.Setup(c => c.ExecuteAsync("xyz")).ReturnsAsync((string?)null);
+        _mockCommand.Setup(c => c.ExecuteAsync("xyz")).ReturnsAsync(new UrbanNotFoundResult());
 
         await _handler.HandleAsync(CreateMessage("_ud xyz"));
 
diff --git a/Bottomly.Tests/Slack/EventHandlers/WikipediaHandlerTests.cs b/Bottomly.Tests/Slack/EventHandlers/WikipediaHandlerTests.cs
index 0f736a3..c81da1e 100644
--- a/Bottomly.Tests/Slack/EventHandlers/WikipediaHandlerTests.cs
+++ b/Bottomly.Tests/Slack/EventHandlers/WikipediaHandlerTests.cs
@@ -19,7 +19,7 @@ public WikipediaHandlerTests()
     {
         var options = TestHelpers.CreateOptions();
         var mockFactory = new Mock<IHttpClientFactory>();
-        _mockCommand = new Mock<WikipediaSearchCommand>(mockFactory.Object);
+        _mockCommand = new Mock<WikipediaSearchCommand>(mockFactory.Object, NullLogger<WikipediaSearchCommand>.Instance);
         _handler = new WikipediaHandler(_mockCommand.Object, _mockBroker.Object, options,
             NullLogger<WikipediaHandler>.Instance);
     }
@@ -36,7 +36,7 @@ private static MessageEvent CreateMessage(string text) =>
     [Fact]
     public async Task HandleAsync_ValidEvent_CallsCommandWithTerm()
     {
-        _mockCommand.Setup(c => c.ExecuteAsync("octopus")).ReturnsAsync((WikipediaResult?)null);
+        _mockCommand.Setup(c => c.ExecuteAsync("octopus")).ReturnsAsync(new WikipediaNotFoundResult());
 
         await _handler.HandleAsync(CreateMessage("_wik octopus"));
 
@@ -47,7 +47,7 @@ public async Task HandleAsync_ValidEvent_CallsCommandWithTerm()
     public async Task HandleAsync_ValidEvent_WithResult_SendsFormattedResponse()
     {
         _mockCommand.Setup(c => c.ExecuteAsync("octopus"))
-            .ReturnsAsync(new WikipediaResult("Octopus", "https://en.wikipedia.org/wiki/Octopus"));
+            .ReturnsAsync(new WikipediaSuccessResult("Octopus", "https://en.wikipedia.org/wiki/Octopus"));
 
         await _handler.HandleAsync(CreateMessage("_wik octopus"));
 
@@ -56,9 +56,9 @@ public async Task HandleAsync_ValidEvent_WithResult_SendsFormattedResponse()
     }
 
     [Fact]
-    public async Task HandleAsync_ValidEvent_NullResult_SendsNoResultMessage()
+    public async Task HandleAsync_ValidEvent_NotFoundResult_SendsNoResultMessage()
     {
-        _mockCommand.Setup(c => c.ExecuteAsync("xyz")).ReturnsAsync((WikipediaResult?)null);
+        _mockCommand.Setup(c => c.ExecuteAsync("xyz")).ReturnsAsync(new WikipediaNotFoundResult());
 
         await _handler.HandleAsync(CreateMessage("_wik xyz"));
 
diff --git a/Bottomly.Tests/Slack/MemberlistPopulatorTests.cs b/Bottomly.Tests/Slack/MemberlistPopulatorTests.cs
index 2b34336..c6147b5 100644
--- a/Bottomly.Tests/Slack/MemberlistPopulatorTests.cs
+++ b/Bottomly.Tests/Slack/MemberlistPopulatorTests.cs
@@ -1,7 +1,6 @@
 using Bottomly.Models;
 using Bottomly.Repositories;
 using Bottomly.Slack;
-using Microsoft.Extensions.Logging.Abstractions;
 using Moq;
 using Shouldly;
 using SlackNet;
@@ -11,9 +10,9 @@ namespace Bottomly.Tests.Slack;
 
 public class MemberlistPopulatorTests
 {
+    private readonly Mock<IMemberRepository> _mockRepo = new();
     private readonly Mock<ISlackApiClient> _mockSlack = new();
     private readonly Mock<IUsersApi> _mockUsers = new();
-    private readonly Mock<IMemberRepository> _mockRepo = new();
     private readonly MemberlistPopulator _populator;
 
     public MemberlistPopulatorTests()
diff --git a/Bottomly.Tests/Slack/MembershipEventHandlers/MemberJoinedEventHandlerTests.cs b/Bottomly.Tests/Slack/MembershipEventHandlers/MemberJoinedEventHandlerTests.cs
index ad5137c..6295036 100644
--- a/Bottomly.Tests/Slack/MembershipEventHandlers/MemberJoinedEventHandlerTests.cs
+++ b/Bottomly.Tests/Slack/MembershipEventHandlers/MemberJoinedEventHandlerTests.cs
@@ -11,10 +11,10 @@ namespace Bottomly.Tests.Slack.MembershipEventHandlers;
 
 public class MemberJoinedEventHandlerTests
 {
+    private readonly MemberJoinedEventHandler _handler;
     private readonly Mock<IMemberRepository> _mockRepo = new();
     private readonly Mock<ISlackApiClient> _mockSlack = new();
     private readonly Mock<IUsersApi> _mockUsers = new();
-    private readonly MemberJoinedEventHandler _handler;
 
     public MemberJoinedEventHandlerTests()
     {
diff --git a/Bottomly.Tests/Slack/MessageEventHandlers/ConversationMessageHandling/ConversationMessageHandlerTests.cs b/Bottomly.Tests/Slack/MessageEventHandlers/ConversationMessageHandling/ConversationMessageHandlerTests.cs
index 9c8147d..49121fa 100644
--- a/Bottomly.Tests/Slack/MessageEventHandlers/ConversationMessageHandling/ConversationMessageHandlerTests.cs
+++ b/Bottomly.Tests/Slack/MessageEventHandlers/ConversationMessageHandling/ConversationMessageHandlerTests.cs
@@ -14,13 +14,13 @@ namespace Bottomly.Tests.Slack.MessageEventHandlers.ConversationMessageHandling;
 
 public class ConversationMessageHandlerTests
 {
-    private readonly Mock<ILlmClient> _mockLlmBroker = new();
-    private readonly Mock<ISlackMessageBroker> _mockSlackBroker = new();
+    private readonly ConversationMessageHandler _handler;
     private readonly Mock<ISlackApiClient> _mockApiClient = new();
     private readonly Mock<IConversationsApi> _mockConversations = new();
-    private readonly Mock<IMemberRepository> _mockMemberRepo = new();
     private readonly Mock<IFeatureFlagRepository> _mockFeatureFlagRepo = new();
-    private readonly ConversationMessageHandler _handler;
+    private readonly Mock<ILlmClient> _mockLlmBroker = new();
+    private readonly Mock<IMemberRepository> _mockMemberRepo = new();
+    private readonly Mock<ISlackMessageBroker> _mockSlackBroker = new();
 
     public ConversationMessageHandlerTests()
     {
@@ -38,7 +38,8 @@ public ConversationMessageHandlerTests()
             NullLogger<ConversationMessageHandler>.Instance);
     }
 
-    private static MessageEvent CreateMessage(string text, string user = "U1", string channel = "C1", string? threadTs = null) =>
+    private static MessageEvent CreateMessage(string text, string user = "U1", string channel = "C1",
+        string? threadTs = null) =>
         new() { Text = text, User = user, Channel = channel, Ts = "ts1", ThreadTs = threadTs };
 
     [Theory]
@@ -70,7 +71,7 @@ public async Task HandleAsync_SuccessfulLlmResponse_SendsReplyToChannel()
         _mockLlmBroker.Setup(b => b.Respond(It.IsAny<BottomlyInputMessage>(), It.IsAny<MessageHistoryContext>()))
             .ReturnsAsync(LlmMessageResponse.Create("Indeed, sir."));
 
-        await _handler.HandleAsync(CreateMessage("bottomly what is 2+2?", "U1", "C1"));
+        await _handler.HandleAsync(CreateMessage("bottomly what is 2+2?"));
 
         _mockSlackBroker.Verify(b => b.SendMessageAsync("Indeed, sir.", "C1", null), Times.Once());
     }
@@ -91,9 +92,10 @@ public async Task HandleAsync_BuildsContextFromHistory()
         _mockLlmBroker.Setup(b => b.Respond(It.IsAny<BottomlyInputMessage>(), It.IsAny<MessageHistoryContext>()))
             .ReturnsAsync(LlmMessageResponse.Create("Of course."));
 
-        await _handler.HandleAsync(CreateMessage("bottomly something", "U1", "C1"));
+        await _handler.HandleAsync(CreateMessage("bottomly something"));
 
-        _mockLlmBroker.Verify(b => b.Respond(It.IsAny<BottomlyInputMessage>(), It.IsAny<MessageHistoryContext>()), Times.Once());
+        _mockLlmBroker.Verify(b => b.Respond(It.IsAny<BottomlyInputMessage>(), It.IsAny<MessageHistoryContext>()),
+            Times.Once());
     }
 
     [Theory]
@@ -113,7 +115,7 @@ public async Task HandleAsync_ErrorLlmResponse_SendsReplyToMessage(string respon
         _mockLlmBroker.Setup(b => b.Respond(It.IsAny<BottomlyInputMessage>(), It.IsAny<MessageHistoryContext>()))
             .ReturnsAsync(errorResponse);
 
-        await _handler.HandleAsync(CreateMessage("bottomly what is 2+2?", "U1", "C1"));
+        await _handler.HandleAsync(CreateMessage("bottomly what is 2+2?"));
 
         _mockSlackBroker.Verify(b => b.SendMessageAsync(It.IsAny<string>(), "C1", "ts1"), Times.Once());
     }
@@ -126,7 +128,7 @@ public async Task HandleAsync_ErrorLlmResponseInThread_SendsReplyToThread()
         _mockLlmBroker.Setup(b => b.Respond(It.IsAny<BottomlyInputMessage>(), It.IsAny<MessageHistoryContext>()))
             .ReturnsAsync(new LlmTimeoutResponse());
 
-        await _handler.HandleAsync(CreateMessage("bottomly what is 2+2?", "U1", "C1", threadTs: "thread_ts1"));
+        await _handler.HandleAsync(CreateMessage("bottomly what is 2+2?", "U1", "C1", "thread_ts1"));
 
         _mockSlackBroker.Verify(b => b.SendMessageAsync(It.IsAny<string>(), "C1", "thread_ts1"), Times.Once());
     }
@@ -136,7 +138,7 @@ public async Task HandleAsync_LlmFlagDisabled_SkipsLlmAndSendsNothing()
     {
         _mockFeatureFlagRepo.Setup(r => r.GetAsync("EnableLlm")).ReturnsAsync(false);
 
-        await _handler.HandleAsync(CreateMessage("bottomly what is 2+2?", "U1", "C1"));
+        await _handler.HandleAsync(CreateMessage("bottomly what is 2+2?"));
 
         _mockLlmBroker.Verify(
             b => b.Respond(It.IsAny<BottomlyInputMessage>(), It.IsAny<MessageHistoryContext>()),
diff --git a/Bottomly.Tests/Slack/ReactionHandlers/AddKarmaReactionHandlerTests.cs b/Bottomly.Tests/Slack/ReactionHandlers/AddKarmaReactionHandlerTests.cs
index 6189f32..2a2da84 100644
--- a/Bottomly.Tests/Slack/ReactionHandlers/AddKarmaReactionHandlerTests.cs
+++ b/Bottomly.Tests/Slack/ReactionHandlers/AddKarmaReactionHandlerTests.cs
@@ -20,7 +20,7 @@ public class AddKarmaReactionHandlerTests
 
     public AddKarmaReactionHandlerTests()
     {
-        var command = new AddKarmaCommand(_mockKarmaRepo.Object);
+        var command = new AddKarmaCommand(_mockKarmaRepo.Object, NullLogger<AddKarmaCommand>.Instance);
         _handler = new AddKarmaReactionHandler(
             command,
             new KarmaReactionMap(),
diff --git a/Bottomly.Tests/Slack/SlackMessageBrokerTests.cs b/Bottomly.Tests/Slack/SlackMessageBrokerTests.cs
index ba8837b..ad9341e 100644
--- a/Bottomly.Tests/Slack/SlackMessageBrokerTests.cs
+++ b/Bottomly.Tests/Slack/SlackMessageBrokerTests.cs
@@ -13,16 +13,11 @@ namespace Bottomly.Tests.Slack;
 
 public class SlackMessageBrokerTests
 {
-    private readonly Mock<IMemberRepository> _mockRepo = new();
-    private readonly Mock<ISlackApiClient> _mockSlack = new();
     private readonly Mock<IChatApi> _mockChat = new();
-    private readonly Mock<IReactionsApi> _mockReactions = new();
     private readonly Mock<IConversationsApi> _mockConversations = new();
-
-    private SlackMessageBroker CreateBroker(string environment = "live") =>
-        new(_mockRepo.Object, _mockSlack.Object,
-            Options.Create(new BottomlyOptions { Environment = environment }),
-            NullLogger<SlackMessageBroker>.Instance);
+    private readonly Mock<IReactionsApi> _mockReactions = new();
+    private readonly Mock<IMemberRepository> _mockRepo = new();
+    private readonly Mock<ISlackApiClient> _mockSlack = new();
 
     public SlackMessageBrokerTests()
     {
@@ -34,6 +29,11 @@ public SlackMessageBrokerTests()
             .Returns(Task.CompletedTask);
     }
 
+    private SlackMessageBroker CreateBroker(string environment = "live") =>
+        new(_mockRepo.Object, _mockSlack.Object,
+            Options.Create(new BottomlyOptions { Environment = environment }),
+            NullLogger<SlackMessageBroker>.Instance);
+
     [Fact]
     public async Task SendMessageAsync_EmptyText_DoesNotPost()
     {
@@ -69,7 +69,7 @@ public async Task SendMessageAsync_WithReplyTs_SetsThreadTs()
     [Fact]
     public async Task SendMessageAsync_DebugMode_PrependsPrefixToText()
     {
-        var broker = CreateBroker(environment: "Dev");
+        var broker = CreateBroker("Dev");
 
         await broker.SendMessageAsync("Hello!", "C1");
 
@@ -107,7 +107,7 @@ public async Task SendBlocksMessageAsync_WithReplyTs_SetsThreadTs()
     [Fact]
     public async Task SendBlocksMessageAsync_DebugMode_PrependsPrefixToText()
     {
-        var broker = CreateBroker(environment: "Dev");
+        var broker = CreateBroker("Dev");
         var blocks = new List<Block> { new ImageBlock { ImageUrl = "https://example.com/img.jpg", AltText = "test" } };
 
         await broker.SendBlocksMessageAsync(blocks, "C1", "fallback");
diff --git a/Bottomly.Tests/Slack/SlackWorkerTests.cs b/Bottomly.Tests/Slack/SlackWorkerTests.cs
index a4e410a..4e88660 100644
--- a/Bottomly.Tests/Slack/SlackWorkerTests.cs
+++ b/Bottomly.Tests/Slack/SlackWorkerTests.cs
@@ -15,9 +15,9 @@ namespace Bottomly.Tests.Slack;
 
 public class SlackWorkerTests
 {
-    private readonly Mock<ISlackSocketModeClient> _mockSocket = new();
     private readonly Mock<ISlackMessageBroker> _mockBroker = new();
     private readonly Mock<IMemberRepository> _mockMemberRepo = new();
+    private readonly Mock<ISlackSocketModeClient> _mockSocket = new();
 
     private SlackWorker CreateWorker(
         IEnumerable<IMessageEventHandler>? handlers = null,
@@ -149,7 +149,7 @@ public async Task ProcessMessageAsync_HelpMessage_RoutesToHelpHandler()
         mockHandler.Setup(h => h.BuildHelpMessage()).Returns("some help text");
 
         var worker = CreateWorker([mockHandler.Object]);
-        await worker.ProcessMessageAsync(CreateMessage("_help", user: "U1"));
+        await worker.ProcessMessageAsync(CreateMessage("_help", "U1"));
 
         _mockBroker.Verify(b => b.SendDmAsync(It.IsAny<string>(), "U1"), Times.Once());
         mockHandler.Verify(h => h.HandleAsync(It.IsAny<MessageEvent>()), Times.Never());
@@ -170,7 +170,7 @@ public async Task ProcessMessageAsync_ResolvesUsernameFromSlackId()
             .Returns(Task.CompletedTask);
 
         var worker = CreateWorker([mockHandler.Object]);
-        await worker.ProcessMessageAsync(CreateMessage("_wiki cats", user: "U1"));
+        await worker.ProcessMessageAsync(CreateMessage("_wiki cats", "U1"));
 
         capturedUser.ShouldBe("alice");
     }
@@ -189,7 +189,7 @@ public async Task ProcessMessageAsync_UnknownSlackId_LeavesUserUnchanged()
             .Returns(Task.CompletedTask);
 
         var worker = CreateWorker([mockHandler.Object]);
-        await worker.ProcessMessageAsync(CreateMessage("_wiki cats", user: "U_UNKNOWN"));
+        await worker.ProcessMessageAsync(CreateMessage("_wiki cats", "U_UNKNOWN"));
 
         capturedUser.ShouldBe("U_UNKNOWN");
     }
diff --git a/Bottomly/AppInitialisation.cs b/Bottomly/AppInitialisation.cs
index d74d2b7..da2e2db 100644
--- a/Bottomly/AppInitialisation.cs
+++ b/Bottomly/AppInitialisation.cs
@@ -23,4 +23,4 @@ public static async Task InitialiseAsync(this IHost app)
             await importer.ImportAsync();
         }
     }
-}
+}
\ No newline at end of file
diff --git a/Bottomly/Commands/AddKarmaCommand.cs b/Bottomly/Commands/AddKarmaCommand.cs
index 73190a7..a1f5de5 100644
--- a/Bottomly/Commands/AddKarmaCommand.cs
+++ b/Bottomly/Commands/AddKarmaCommand.cs
@@ -1,29 +1,43 @@
 using Bottomly.Models;
 using Bottomly.Repositories;
+using Microsoft.Extensions.Logging;
 
 namespace Bottomly.Commands;
 
-public class AddKarmaCommand(IKarmaRepository karmaRepository) : ICommand
+public abstract record AddKarmaResult;
+public record AddKarmaSuccessResult(Karma Karma) : AddKarmaResult;
+public record AddKarmaSelfAwardResult : AddKarmaResult;
+public record AddKarmaErrorResult(string Error) : AddKarmaResult;
+
+public class AddKarmaCommand(IKarmaRepository karmaRepository, ILogger<AddKarmaCommand> logger) : ICommand
 {
     public string GetPurpose() => "Awards an imaginary internet point to someone/something.";
 
-    public async Task<Karma> ExecuteAsync(string awardedTo, string awardedBy, string reason, KarmaType karmaType)
+    public async Task<AddKarmaResult> ExecuteAsync(string awardedTo, string awardedBy, string reason, KarmaType karmaType)
     {
         if (karmaType == KarmaType.PozzyPoz && awardedBy.Equals(awardedTo, StringComparison.OrdinalIgnoreCase))
         {
-            throw new InvalidOperationException("Can't give yourself positive karma");
+            return new AddKarmaSelfAwardResult();
         }
 
-        var karma = new Karma
+        try
         {
-            AwardedToUsername = awardedTo,
-            AwardedByUsername = awardedBy,
-            Reason = reason,
-            Awarded = DateTime.UtcNow,
-            KarmaType = karmaType
-        };
+            var karma = new Karma
+            {
+                AwardedToUsername = awardedTo,
+                AwardedByUsername = awardedBy,
+                Reason = reason,
+                Awarded = DateTime.UtcNow,
+                KarmaType = karmaType
+            };
 
-        await karmaRepository.AddAsync(karma);
-        return karma;
+            await karmaRepository.AddAsync(karma);
+            return new AddKarmaSuccessResult(karma);
+        }
+        catch (Exception ex)
+        {
+            logger.LogError(ex, "Error adding karma for {AwardedTo}", awardedTo);
+            return new AddKarmaErrorResult(ex.Message);
+        }
     }
 }
\ No newline at end of file
diff --git a/Bottomly/Commands/GiphyCommand.cs b/Bottomly/Commands/GiphyCommand.cs
index 511914a..839bb4c 100644
--- a/Bottomly/Commands/GiphyCommand.cs
+++ b/Bottomly/Commands/GiphyCommand.cs
@@ -39,7 +39,7 @@ public virtual async Task<GiphyResult> ExecuteAsync(string searchTerm)
                 return new GiphyEmptyResult();
             }
 
-            var gifUrl = data.GetProperty("url").GetString();
+            var gifUrl = data.GetProperty("images").GetProperty("original").GetProperty("url").GetString();
             return string.IsNullOrEmpty(gifUrl)
                 ? new GiphyEmptyResult()
                 : new GiphySuccessResult(gifUrl);
diff --git a/Bottomly/Commands/ReleaseCommand.cs b/Bottomly/Commands/ReleaseCommand.cs
index 124b3fd..fc42d02 100644
--- a/Bottomly/Commands/ReleaseCommand.cs
+++ b/Bottomly/Commands/ReleaseCommand.cs
@@ -5,6 +5,10 @@
 
 namespace Bottomly.Commands;
 
+public abstract record ReleaseResult;
+public record ReleaseSuccessResult(string Description) : ReleaseResult;
+public record ReleaseErrorResult : ReleaseResult;
+
 public class ReleaseCommand(IOptions<BottomlyOptions> options, ILogger<ReleaseCommand> logger)
     : ICommand
 {
@@ -12,7 +16,7 @@ public class ReleaseCommand(IOptions<BottomlyOptions> options, ILogger<ReleaseCo
 
     public string GetPurpose() => "Describes the latest release of bottomly";
 
-    public virtual async Task<string?> ExecuteAsync()
+    public virtual async Task<ReleaseResult> ExecuteAsync()
     {
         try
         {
@@ -31,12 +35,12 @@ public class ReleaseCommand(IOptions<BottomlyOptions> options, ILogger<ReleaseCo
                 desc += $"\n{release.Body}";
             }
 
-            return desc;
+            return new ReleaseSuccessResult(desc);
         }
         catch (Exception ex)
         {
             logger.LogError(ex, "Error retrieving release info from Github");
-            return null;
+            return new ReleaseErrorResult();
         }
     }
 }
\ No newline at end of file
diff --git a/Bottomly/Commands/UrbanSearchCommand.cs b/Bottomly/Commands/UrbanSearchCommand.cs
index d870867..fab8304 100644
--- a/Bottomly/Commands/UrbanSearchCommand.cs
+++ b/Bottomly/Commands/UrbanSearchCommand.cs
@@ -1,34 +1,52 @@
 using System.Text.Json;
+using Microsoft.Extensions.Logging;
 
 namespace Bottomly.Commands;
 
-public class UrbanSearchCommand(IHttpClientFactory httpClientFactory) : ICommand
+public abstract record UrbanResult;
+public record UrbanSuccessResult(string Definition) : UrbanResult;
+public record UrbanNotFoundResult : UrbanResult;
+public record UrbanEmptyInputResult : UrbanResult;
+public record UrbanErrorResult(string Error) : UrbanResult;
+
+public class UrbanSearchCommand(IHttpClientFactory httpClientFactory, ILogger<UrbanSearchCommand> logger) : ICommand
 {
     private readonly IHttpClientFactory _httpClientFactory = httpClientFactory;
 
     public string GetPurpose() => "Tells you what something _really_ means.";
 
-    public virtual async Task<string?> ExecuteAsync(string searchTerm)
+    public virtual async Task<UrbanResult> ExecuteAsync(string searchTerm)
     {
         if (string.IsNullOrWhiteSpace(searchTerm))
         {
-            return null;
+            return new UrbanEmptyInputResult();
         }
 
-        var url = $"http://api.urbandictionary.com/v0/define?term={Uri.EscapeDataString(searchTerm)}";
-        var httpClient = _httpClientFactory.CreateClient();
-        var response = await httpClient.GetAsync(url);
-        response.EnsureSuccessStatusCode();
-
-        using var doc = JsonDocument.Parse(await response.Content.ReadAsStringAsync());
-        var list = doc.RootElement.GetProperty("list");
-
-        if (list.GetArrayLength() == 0)
+        try
         {
-            return null;
+            var url = $"http://api.urbandictionary.com/v0/define?term={Uri.EscapeDataString(searchTerm)}";
+            var httpClient = _httpClientFactory.CreateClient();
+            var response = await httpClient.GetAsync(url);
+            response.EnsureSuccessStatusCode();
+
+            using var doc = JsonDocument.Parse(await response.Content.ReadAsStringAsync());
+            var list = doc.RootElement.GetProperty("list");
+
+            if (list.GetArrayLength() == 0)
+            {
+                return new UrbanNotFoundResult();
+            }
+
+            var index = Random.Shared.Next(list.GetArrayLength());
+            var definition = list[index].GetProperty("definition").GetString();
+            return definition is not null
+                ? new UrbanSuccessResult(definition)
+                : new UrbanNotFoundResult();
+        }
+        catch (Exception ex)
+        {
+            logger.LogError(ex, "Error executing Urban Dictionary search");
+            return new UrbanErrorResult(ex.Message);
         }
-
-        var index = Random.Shared.Next(list.GetArrayLength());
-        return list[index].GetProperty("definition").GetString();
     }
 }
\ No newline at end of file
diff --git a/Bottomly/Commands/WikipediaSearchCommand.cs b/Bottomly/Commands/WikipediaSearchCommand.cs
index 9c46ab6..132a406 100644
--- a/Bottomly/Commands/WikipediaSearchCommand.cs
+++ b/Bottomly/Commands/WikipediaSearchCommand.cs
@@ -1,44 +1,51 @@
 using System.Text.Json;
+using Microsoft.Extensions.Logging;
 
 namespace Bottomly.Commands;
 
-public record WikipediaResult(string Text, string Link);
+public abstract record WikipediaResult;
+public record WikipediaSuccessResult(string Text, string Link) : WikipediaResult;
+public record WikipediaNotFoundResult : WikipediaResult;
+public record WikipediaEmptyInputResult : WikipediaResult;
+public record WikipediaErrorResult(string Error) : WikipediaResult;
 
-public class WikipediaSearchCommand(IHttpClientFactory httpClientFactory) : ICommand
+public class WikipediaSearchCommand(IHttpClientFactory httpClientFactory, ILogger<WikipediaSearchCommand> logger) : ICommand
 {
     private readonly IHttpClientFactory _httpClientFactory = httpClientFactory;
 
-    public string GetPurpose()
-    {
-        return "Performs a wikipedia search and returns the top hit.";
-    }
+    public string GetPurpose() => "Performs a wikipedia search and returns the top hit.";
 
-    public virtual async Task<WikipediaResult?> ExecuteAsync(string searchTerm)
+    public virtual async Task<WikipediaResult> ExecuteAsync(string searchTerm)
     {
         if (string.IsNullOrWhiteSpace(searchTerm))
         {
-            return null;
+            return new WikipediaEmptyInputResult();
         }
 
-        var url =
-            $"https://en.wikipedia.org/w/api.php?action=opensearch&format=json&search={Uri.EscapeDataString(searchTerm)}";
-        var httpClient = _httpClientFactory.CreateClient();
-        httpClient.DefaultRequestHeaders.UserAgent.ParseAdd("Bottomly/1.0");
-        var response = await httpClient.GetAsync(url);
-        response.EnsureSuccessStatusCode();
-
-        using var doc = JsonDocument.Parse(await response.Content.ReadAsStringAsync());
-        var root = doc.RootElement;
-
-        // Response is: [searchTerm, [titles], [descriptions], [links]]
-        var titles = root[1];
-        var links = root[3];
-
-        if (titles.GetArrayLength() == 0)
+        try
         {
-            return null;
+            var url =
+                $"https://en.wikipedia.org/w/api.php?action=opensearch&format=json&search={Uri.EscapeDataString(searchTerm)}";
+            var httpClient = _httpClientFactory.CreateClient();
+            httpClient.DefaultRequestHeaders.UserAgent.ParseAdd("Bottomly/1.0");
+            var response = await httpClient.GetAsync(url);
+            response.EnsureSuccessStatusCode();
+
+            using var doc = JsonDocument.Parse(await response.Content.ReadAsStringAsync());
+            var root = doc.RootElement;
+
+            // Response is: [searchTerm, [titles], [descriptions], [links]]
+            var titles = root[1];
+            var links = root[3];
+
+            return titles.GetArrayLength() == 0
+                ? new WikipediaNotFoundResult()
+                : new WikipediaSuccessResult(titles[0].GetString()!, links[0].GetString()!);
+        }
+        catch (Exception ex)
+        {
+            logger.LogError(ex, "Error executing Wikipedia search");
+            return new WikipediaErrorResult(ex.Message);
         }
-
-        return new WikipediaResult(titles[0].GetString()!, links[0].GetString()!);
     }
 }
\ No newline at end of file
diff --git a/Bottomly/Configuration/ServiceCollectionExtensions.cs b/Bottomly/Configuration/ServiceCollectionExtensions.cs
index f36e971..2bd0303 100644
--- a/Bottomly/Configuration/ServiceCollectionExtensions.cs
+++ b/Bottomly/Configuration/ServiceCollectionExtensions.cs
@@ -5,7 +5,8 @@ namespace Bottomly.Configuration;
 
 public static class ServiceCollectionExtensions
 {
-    public static IServiceCollection AddBottomlyConfiguration(this IServiceCollection services, IConfiguration configuration)
+    public static IServiceCollection AddBottomlyConfiguration(this IServiceCollection services,
+        IConfiguration configuration)
     {
         services.Configure<BottomlyOptions>(opts =>
         {
@@ -23,4 +24,4 @@ public static IServiceCollection AddBottomlyConfiguration(this IServiceCollectio
 
         return services;
     }
-}
+}
\ No newline at end of file
diff --git a/Bottomly/HostBuilderExtensions.cs b/Bottomly/HostBuilderExtensions.cs
index 184e418..dd7d2fa 100644
--- a/Bottomly/HostBuilderExtensions.cs
+++ b/Bottomly/HostBuilderExtensions.cs
@@ -25,4 +25,4 @@ public void RegisterCommands(Assembly assembly) =>
                 .ToList()
                 .ForEach(t => builder.Services.AddSingleton(t));
     }
-}
+}
\ No newline at end of file
diff --git a/Bottomly/LlmBot/ServiceCollectionExtensions.cs b/Bottomly/LlmBot/ServiceCollectionExtensions.cs
index 7497075..67b20ae 100644
--- a/Bottomly/LlmBot/ServiceCollectionExtensions.cs
+++ b/Bottomly/LlmBot/ServiceCollectionExtensions.cs
@@ -34,4 +34,4 @@ public static IHostApplicationBuilder AddBottomlyLlm(this IHostApplicationBuilde
 
         return builder;
     }
-}
+}
\ No newline at end of file
diff --git a/Bottomly/Models/FeatureFlag.cs b/Bottomly/Models/FeatureFlag.cs
index 6c578a4..b4ab9f2 100644
--- a/Bottomly/Models/FeatureFlag.cs
+++ b/Bottomly/Models/FeatureFlag.cs
@@ -4,7 +4,7 @@ namespace Bottomly.Models;
 
 public class FeatureFlag
 {
-    [BsonId][BsonElement("_id")] public string Id { get; set; } = string.Empty;
+    [BsonId] [BsonElement("_id")] public string Id { get; set; } = string.Empty;
 
     [BsonElement("enabled")] public bool Enabled { get; set; }
-}
+}
\ No newline at end of file
diff --git a/Bottomly/Models/Karma.cs b/Bottomly/Models/Karma.cs
index 2bd7a2c..a75dcf7 100644
--- a/Bottomly/Models/Karma.cs
+++ b/Bottomly/Models/Karma.cs
@@ -22,9 +22,10 @@ public class Karma
     [BsonElement("karma_type")] public string KarmaTypeValue { get; set; } = string.Empty;
 
     /// <summary>
-    /// Legacy element to enable support from pymongo persisted data
+    ///     Legacy element to enable support from pymongo persisted data
     /// </summary>
-    [BsonElement("_cls")] public string Cls { get; set; } = string.Empty;
+    [BsonElement("_cls")]
+    public string Cls { get; set; } = string.Empty;
 
     [BsonIgnore]
     public KarmaType KarmaType
diff --git a/Bottomly/Models/Member.cs b/Bottomly/Models/Member.cs
index 11f2770..eae6c81 100644
--- a/Bottomly/Models/Member.cs
+++ b/Bottomly/Models/Member.cs
@@ -4,7 +4,7 @@ namespace Bottomly.Models;
 
 public class Member
 {
-    [BsonId][BsonElement("_id")] public string Username { get; set; } = string.Empty;
+    [BsonId] [BsonElement("_id")] public string Username { get; set; } = string.Empty;
 
     [BsonElement("slack_id")] public string SlackId { get; set; } = string.Empty;
 
diff --git a/Bottomly/Repositories/CachingMemberRepository.cs b/Bottomly/Repositories/CachingMemberRepository.cs
index fec0737..628cc1c 100644
--- a/Bottomly/Repositories/CachingMemberRepository.cs
+++ b/Bottomly/Repositories/CachingMemberRepository.cs
@@ -12,29 +12,42 @@ public async Task<List<Member>> GetAllAsync()
     {
         var members = await inner.GetAllAsync();
         foreach (var member in members)
+        {
             CacheMember(member);
+        }
+
         return members;
     }
 
     public async Task<Member?> GetByUsernameAsync(string username)
     {
         if (cache.TryGetValue(UsernameKeyPrefix + username, out Member? cached))
+        {
             return cached;
+        }
 
         var member = await inner.GetByUsernameAsync(username);
         if (member is not null)
+        {
             CacheMember(member);
+        }
+
         return member;
     }
 
     public async Task<Member?> GetBySlackIdAsync(string slackId)
     {
         if (cache.TryGetValue(SlackKeyPrefix + slackId, out Member? cached))
+        {
             return cached;
+        }
 
         var member = await inner.GetBySlackIdAsync(slackId);
         if (member is not null)
+        {
             CacheMember(member);
+        }
+
         return member;
     }
 
@@ -47,9 +60,13 @@ public async Task<List<Member>> GetBySlackIdsAsync(IEnumerable<string> slackIds)
         foreach (var id in idList)
         {
             if (cache.TryGetValue(SlackKeyPrefix + id, out Member? cached))
+            {
                 result.Add(cached!);
+            }
             else
+            {
                 misses.Add(id);
+            }
         }
 
         if (misses.Count > 0)
@@ -76,17 +93,24 @@ public async Task AddAsync(IEnumerable<Member> members)
         var memberList = members.ToList();
         await inner.AddAsync(memberList);
         foreach (var member in memberList)
+        {
             CacheMember(member);
+        }
     }
 
-    public async Task UpdateInfoAsync(string username, string fullName, Gender gender, SassLevel sassLevel, string miscInfo)
+    public async Task UpdateInfoAsync(string username, string fullName, Gender gender, SassLevel sassLevel,
+        string miscInfo)
     {
         await inner.UpdateInfoAsync(username, fullName, gender, sassLevel, miscInfo);
         var updated = await inner.GetByUsernameAsync(username);
         if (updated is not null)
+        {
             CacheMember(updated);
+        }
         else
+        {
             cache.Remove(UsernameKeyPrefix + username);
+        }
     }
 
     private void CacheMember(Member member)
@@ -94,4 +118,4 @@ private void CacheMember(Member member)
         cache.Set(SlackKeyPrefix + member.SlackId, member);
         cache.Set(UsernameKeyPrefix + member.Username, member);
     }
-}
+}
\ No newline at end of file
diff --git a/Bottomly/Repositories/FeatureFlagRepository.cs b/Bottomly/Repositories/FeatureFlagRepository.cs
index 0dbfc47..6a7b300 100644
--- a/Bottomly/Repositories/FeatureFlagRepository.cs
+++ b/Bottomly/Repositories/FeatureFlagRepository.cs
@@ -27,4 +27,4 @@ public async Task SeedAsync(string flagId, bool defaultValue)
         var update = Builders<FeatureFlag>.Update.SetOnInsert(f => f.Enabled, defaultValue);
         await _collection.UpdateOneAsync(filter, update, new UpdateOptions { IsUpsert = true });
     }
-}
+}
\ No newline at end of file
diff --git a/Bottomly/Repositories/IFeatureFlagRepository.cs b/Bottomly/Repositories/IFeatureFlagRepository.cs
index 805b29f..442dcb0 100644
--- a/Bottomly/Repositories/IFeatureFlagRepository.cs
+++ b/Bottomly/Repositories/IFeatureFlagRepository.cs
@@ -5,4 +5,4 @@ public interface IFeatureFlagRepository
     Task<bool> GetAsync(string flagId);
     Task SetAsync(string flagId, bool enabled);
     Task SeedAsync(string flagId, bool defaultValue);
-}
+}
\ No newline at end of file
diff --git a/Bottomly/Repositories/MemberCachePopulator.cs b/Bottomly/Repositories/MemberCachePopulator.cs
index 6a738ca..2abf7e2 100644
--- a/Bottomly/Repositories/MemberCachePopulator.cs
+++ b/Bottomly/Repositories/MemberCachePopulator.cs
@@ -13,4 +13,4 @@ public async Task StartAsync(CancellationToken cancellationToken)
     }
 
     public Task StopAsync(CancellationToken cancellationToken) => Task.CompletedTask;
-}
+}
\ No newline at end of file
diff --git a/Bottomly/Repositories/MemberRepository.cs b/Bottomly/Repositories/MemberRepository.cs
index b69a853..aa9a337 100644
--- a/Bottomly/Repositories/MemberRepository.cs
+++ b/Bottomly/Repositories/MemberRepository.cs
@@ -22,7 +22,8 @@ public Task<List<Member>> GetBySlackIdsAsync(IEnumerable<string> slackIds) =>
     public async Task AddAsync(Member member) => await _collection.InsertOneAsync(member);
     public async Task AddAsync(IEnumerable<Member> members) => await _collection.InsertManyAsync(members);
 
-    public async Task UpdateInfoAsync(string username, string fullName, Gender gender, SassLevel sassLevel, string miscInfo)
+    public async Task UpdateInfoAsync(string username, string fullName, Gender gender, SassLevel sassLevel,
+        string miscInfo)
     {
         var update = Builders<Member>.Update
             .Set(m => m.FullName, fullName)
diff --git a/Bottomly/Repositories/ServiceCollectionExtensions.cs b/Bottomly/Repositories/ServiceCollectionExtensions.cs
index 8c71e45..a50d41b 100644
--- a/Bottomly/Repositories/ServiceCollectionExtensions.cs
+++ b/Bottomly/Repositories/ServiceCollectionExtensions.cs
@@ -18,4 +18,4 @@ public static IServiceCollection AddBottomlyRepositories(this IServiceCollection
 
         return services;
     }
-}
+}
\ No newline at end of file
diff --git a/Bottomly/Seed/MemberSeedDataImporter.cs b/Bottomly/Seed/MemberSeedDataImporter.cs
index e1a43d8..9cf3ca6 100644
--- a/Bottomly/Seed/MemberSeedDataImporter.cs
+++ b/Bottomly/Seed/MemberSeedDataImporter.cs
@@ -50,6 +50,7 @@ private string ResolveSeedDir()
 
             dir = dir.Parent;
         }
+
         return Path.Combine(env.ContentRootPath, "MemberSeedData");
     }
 
@@ -60,15 +61,17 @@ private async Task ImportFileAsync(string file)
             var yaml = await File.ReadAllTextAsync(file);
             var dto = _deserializer.Deserialize<MemberSeedDataDto>(yaml);
 
-            if (!Enum.TryParse<Gender>(dto.Gender, ignoreCase: true, out var gender))
+            if (!Enum.TryParse<Gender>(dto.Gender, true, out var gender))
             {
-                logger.LogWarning("Unknown gender value '{Value}' in {File}. Defaulting to Unknown.", dto.Gender, Path.GetFileName(file));
+                logger.LogWarning("Unknown gender value '{Value}' in {File}. Defaulting to Unknown.", dto.Gender,
+                    Path.GetFileName(file));
                 gender = Gender.Unknown;
             }
 
-            if (!Enum.TryParse<SassLevel>(dto.SassLevel, ignoreCase: true, out var sassLevel))
+            if (!Enum.TryParse<SassLevel>(dto.SassLevel, true, out var sassLevel))
             {
-                logger.LogWarning("Unknown sass_level value '{Value}' in {File}. Defaulting to Moderate.", dto.SassLevel, Path.GetFileName(file));
+                logger.LogWarning("Unknown sass_level value '{Value}' in {File}. Defaulting to Moderate.",
+                    dto.SassLevel, Path.GetFileName(file));
                 sassLevel = SassLevel.Moderate;
             }
 
diff --git a/Bottomly/Seed/ServiceCollectionExtensions.cs b/Bottomly/Seed/ServiceCollectionExtensions.cs
index 544c4de..a85bb3c 100644
--- a/Bottomly/Seed/ServiceCollectionExtensions.cs
+++ b/Bottomly/Seed/ServiceCollectionExtensions.cs
@@ -12,4 +12,4 @@ public static IServiceCollection AddBottomlySeeding(this IServiceCollection serv
 
         return services;
     }
-}
+}
\ No newline at end of file
diff --git a/Bottomly/Slack/ISlackMessageBroker.cs b/Bottomly/Slack/ISlackMessageBroker.cs
index 2d33984..dd7b3af 100644
--- a/Bottomly/Slack/ISlackMessageBroker.cs
+++ b/Bottomly/Slack/ISlackMessageBroker.cs
@@ -5,7 +5,10 @@ namespace Bottomly.Slack;
 public interface ISlackMessageBroker
 {
     Task SendMessageAsync(string text, string channel, string? replyToTs = null);
-    Task SendBlocksMessageAsync(IReadOnlyList<Block> blocks, string channel, string? text = null, string? replyToTs = null);
+
+    Task SendBlocksMessageAsync(IReadOnlyList<Block> blocks, string channel, string? text = null,
+        string? replyToTs = null);
+
     Task SendReactionAsync(string emoji, string channel, string timestamp);
     Task SendDmAsync(string text, string username);
 }
\ No newline at end of file
diff --git a/Bottomly/Slack/MessageEventHandlers/AbstractMessageEventHandler.cs b/Bottomly/Slack/MessageEventHandlers/AbstractMessageEventHandler.cs
index 0d1f14b..64b4dde 100644
--- a/Bottomly/Slack/MessageEventHandlers/AbstractMessageEventHandler.cs
+++ b/Bottomly/Slack/MessageEventHandlers/AbstractMessageEventHandler.cs
@@ -74,7 +74,8 @@ protected async Task SendMessageResponseAsync(string text, MessageEvent message,
         await Broker.SendMessageAsync(text, message.Channel, replyTs);
     }
 
-    protected async Task SendBlocksResponseAsync(IReadOnlyList<Block> blocks, MessageEvent message, string? text = null, bool asReply = false)
+    protected async Task SendBlocksResponseAsync(IReadOnlyList<Block> blocks, MessageEvent message, string? text = null,
+        bool asReply = false)
     {
         var replyTs = asReply ? message.TsForReply() : null;
         await Broker.SendBlocksMessageAsync(blocks, message.Channel, text, replyTs);
diff --git a/Bottomly/Slack/MessageEventHandlers/ConversationMessageHandling/ConversationMessageHandler.cs b/Bottomly/Slack/MessageEventHandlers/ConversationMessageHandling/ConversationMessageHandler.cs
index e462c86..0fd2df7 100644
--- a/Bottomly/Slack/MessageEventHandlers/ConversationMessageHandling/ConversationMessageHandler.cs
+++ b/Bottomly/Slack/MessageEventHandlers/ConversationMessageHandling/ConversationMessageHandler.cs
@@ -20,10 +20,14 @@ ILogger<ConversationMessageHandler> logger
 
     public bool CanHandle(MessageEvent message)
     {
-        if (message.Text.Contains("bottomly")) return true;
+        if (message.Text.Contains("bottomly"))
+        {
+            return true;
+        }
+
         return _botMemberTask.IsCompletedSuccessfully
-            && _botMemberTask.Result?.SlackId is { } botId
-            && message.Text.Contains($"<@{botId}>");
+               && _botMemberTask.Result?.SlackId is { } botId
+               && message.Text.Contains($"<@{botId}>");
     }
 
     public async Task HandleAsync(MessageEvent message)
diff --git a/Bottomly/Slack/MessageEventHandlers/KarmaEventHandlers/AbstractMessageKarmaEventHandler.cs b/Bottomly/Slack/MessageEventHandlers/KarmaEventHandlers/AbstractMessageKarmaEventHandler.cs
index 7675448..a435b6e 100644
--- a/Bottomly/Slack/MessageEventHandlers/KarmaEventHandlers/AbstractMessageKarmaEventHandler.cs
+++ b/Bottomly/Slack/MessageEventHandlers/KarmaEventHandlers/AbstractMessageKarmaEventHandler.cs
@@ -36,12 +36,24 @@ public override bool CanHandle(MessageEvent message) =>
     protected override async Task InvokeHandlerLogicAsync(MessageEvent message)
     {
         var args = await ParseCommandTextAsync(message.Text!);
-        await KarmaCommand.ExecuteAsync(
+        var result = await KarmaCommand.ExecuteAsync(
             args.Recipient,
             message.User,
             args.Reason,
             args.KarmaType);
-        await SendReactionResponseAsync(message);
+
+        switch (result)
+        {
+            case AddKarmaSuccessResult:
+                await SendReactionResponseAsync(message);
+                break;
+            case AddKarmaSelfAwardResult:
+                await SendMessageResponseAsync("Can't give yourself positive karma", message);
+                break;
+            case AddKarmaErrorResult error:
+                Logger.LogError("Karma command failed: {Error}", error.Error);
+                break;
+        }
     }
 
     private async Task<KarmaArgs> ParseCommandTextAsync(string commandText)
diff --git a/Bottomly/Slack/MessageEventHandlers/ReleaseHandler.cs b/Bottomly/Slack/MessageEventHandlers/ReleaseHandler.cs
index ec8cc69..8d5a0a1 100644
--- a/Bottomly/Slack/MessageEventHandlers/ReleaseHandler.cs
+++ b/Bottomly/Slack/MessageEventHandlers/ReleaseHandler.cs
@@ -21,7 +21,11 @@ public class ReleaseHandler(
     protected override async Task InvokeHandlerLogicAsync(MessageEvent message)
     {
         var result = await command.ExecuteAsync();
-        var response = result ?? "Unable to retrieve latest release info.";
+        var response = result switch
+        {
+            ReleaseSuccessResult success => success.Description,
+            _ => "Unable to retrieve latest release info."
+        };
         await SendMessageResponseAsync(response, message);
     }
 }
\ No newline at end of file
diff --git a/Bottomly/Slack/MessageEventHandlers/SearchHandler.cs b/Bottomly/Slack/MessageEventHandlers/SearchHandler.cs
index ea89fe4..d6dbad3 100644
--- a/Bottomly/Slack/MessageEventHandlers/SearchHandler.cs
+++ b/Bottomly/Slack/MessageEventHandlers/SearchHandler.cs
@@ -18,10 +18,7 @@ public class SearchHandler(
     protected override ICommand Command => command;
     protected override string CommandSymbol => "g";
 
-    protected override string GetUsage()
-    {
-        return CommandTrigger + "<query>";
-    }
+    protected override string GetUsage() => CommandTrigger + "<query>";
 
     protected override async Task InvokeHandlerLogicAsync(MessageEvent message)
     {
diff --git a/Bottomly/Slack/MessageEventHandlers/UrbanHandler.cs b/Bottomly/Slack/MessageEventHandlers/UrbanHandler.cs
index 7745bfb..90d4ba8 100644
--- a/Bottomly/Slack/MessageEventHandlers/UrbanHandler.cs
+++ b/Bottomly/Slack/MessageEventHandlers/UrbanHandler.cs
@@ -22,7 +22,11 @@ protected override async Task InvokeHandlerLogicAsync(MessageEvent message)
     {
         var term = message.Text![CommandTrigger.Length..];
         var result = await command.ExecuteAsync(term);
-        var response = result ?? "Left as an exercise for the reader.";
+        var response = result switch
+        {
+            UrbanSuccessResult success => success.Definition,
+            _ => "Left as an exercise for the reader."
+        };
         await SendMessageResponseAsync(response, message, true);
     }
 }
\ No newline at end of file
diff --git a/Bottomly/Slack/MessageEventHandlers/WikipediaHandler.cs b/Bottomly/Slack/MessageEventHandlers/WikipediaHandler.cs
index 95f4ef4..7c44c99 100644
--- a/Bottomly/Slack/MessageEventHandlers/WikipediaHandler.cs
+++ b/Bottomly/Slack/MessageEventHandlers/WikipediaHandler.cs
@@ -22,9 +22,14 @@ protected override async Task InvokeHandlerLogicAsync(MessageEvent message)
     {
         var term = message.Text![CommandTrigger.Length..];
         var result = await command.ExecuteAsync(term);
-        var response = result is null
-            ? $"No results found for \"{term}\""
-            : $"<{result.Link}|{result.Text}>";
+        var response = result switch
+        {
+            WikipediaSuccessResult success => $"<{success.Link}|{success.Text}>",
+            WikipediaNotFoundResult => $"No results found for \"{term}\"",
+            WikipediaEmptyInputResult => $"No results found for \"{term}\"",
+            WikipediaErrorResult => $"No results found for \"{term}\"",
+            _ => $"No results found for \"{term}\""
+        };
         await SendMessageResponseAsync(response, message);
     }
 }
\ No newline at end of file
diff --git a/Bottomly/Slack/ReactionHandlers/AddKarmaReactionHandler.cs b/Bottomly/Slack/ReactionHandlers/AddKarmaReactionHandler.cs
index 55a11a7..1c49ebd 100644
--- a/Bottomly/Slack/ReactionHandlers/AddKarmaReactionHandler.cs
+++ b/Bottomly/Slack/ReactionHandlers/AddKarmaReactionHandler.cs
@@ -36,13 +36,13 @@ public async Task HandleAsync(ReactionAdded reactionEvent)
                 return;
             }
 
-            await command.ExecuteAsync(
+            var result = await command.ExecuteAsync(
                 reactee.Username,
                 reactor.Username,
                 $"Reacted with {reaction}",
                 reactionMap.GetKarmaType(reaction));
 
-            if (reactionEvent.Item is ReactionMessage messageItem)
+            if (result is AddKarmaSuccessResult && reactionEvent.Item is ReactionMessage messageItem)
             {
                 await broker.SendReactionAsync("robot_face", messageItem.Channel, messageItem.Ts);
             }
diff --git a/Bottomly/Slack/ServiceCollectionExtensions.cs b/Bottomly/Slack/ServiceCollectionExtensions.cs
index d39d11f..45ea9a7 100644
--- a/Bottomly/Slack/ServiceCollectionExtensions.cs
+++ b/Bottomly/Slack/ServiceCollectionExtensions.cs
@@ -48,4 +48,4 @@ public static IServiceCollection AddBottomlySlack(this IServiceCollection servic
 
         return services;
     }
-}
+}
\ No newline at end of file
diff --git a/Bottomly/Slack/SlackMessageBroker.cs b/Bottomly/Slack/SlackMessageBroker.cs
index 27fc152..5079002 100644
--- a/Bottomly/Slack/SlackMessageBroker.cs
+++ b/Bottomly/Slack/SlackMessageBroker.cs
@@ -45,7 +45,8 @@ public async Task SendMessageAsync(string text, string channel, string? replyToT
         }
     }
 
-    public async Task SendBlocksMessageAsync(IReadOnlyList<Block> blocks, string channel, string? text = null, string? replyToTs = null)
+    public async Task SendBlocksMessageAsync(IReadOnlyList<Block> blocks, string channel, string? text = null,
+        string? replyToTs = null)
     {
         try
         {
diff --git a/Bottomly/Slack/SlackWorker.cs b/Bottomly/Slack/SlackWorker.cs
index 444d4b1..39cffb6 100644
--- a/Bottomly/Slack/SlackWorker.cs
+++ b/Bottomly/Slack/SlackWorker.cs
@@ -1,4 +1,3 @@
-using Bottomly.LlmBot;
 using Bottomly.Repositories;
 using Bottomly.Slack.MessageEventHandlers;
 using Bottomly.Slack.ReactionHandlers;
diff --git a/README.md b/README.md
index 2b58a1c..ba847ec 100644
--- a/README.md
+++ b/README.md
@@ -8,7 +8,8 @@ A .NET Slack bot
 
 ### Development
 
-The project uses [.NET Aspire](https://learn.microsoft.com/en-us/dotnet/aspire/get-started/aspire-overview) for local orchestration. Running the `Bottomly.AppHost` project will spin up MongoDB, Ollama (LLM), and the bot itself:
+The project uses [.NET Aspire](https://learn.microsoft.com/en-us/dotnet/aspire/get-started/aspire-overview) for local
+orchestration. Running the `Bottomly.AppHost` project will spin up MongoDB, Ollama (LLM), and the bot itself:
 
 ```bash
 dotnet run --project Bottomly.AppHost
@@ -16,7 +17,8 @@ dotnet run --project Bottomly.AppHost
 
 ### Production
 
-Run the `Bottomly` project directly, ensuring MongoDB and Ollama are available and all required environment variables are set:
+Run the `Bottomly` project directly, ensuring MongoDB and Ollama are available and all required environment variables
+are set:
 
 ```bash
 dotnet run --project Bottomly
@@ -35,27 +37,31 @@ Within the `Bottomly` project, code is organised by responsibility:
 
 ### Commands
 
-Classes here implement the actions triggered by bot commands. Each command performs an action and returns a result, delegating any persistence work to the `Repositories` layer.
+Classes here implement the actions triggered by bot commands. Each command performs an action and returns a result,
+delegating any persistence work to the `Repositories` layer.
 
 ### Repositories
 
-Defines the persistence layer. All behaviours which relate to persisting information beyond a simple request/response cycle are defined here, e.g. user karma and member lists. Backed by MongoDB.
+Defines the persistence layer. All behaviours which relate to persisting information beyond a simple request/response
+cycle are defined here, e.g. user karma and member lists. Backed by MongoDB.
 
 ### Slack
 
 Implements the Slack delivery channel using [SlackNet](https://github.com/soxtoby/SlackNet) in Socket Mode.
 
-`SlackWorker` is a background service that maintains the Slack connection and dispatches incoming events. Event handlers are split by type:
+`SlackWorker` is a background service that maintains the Slack connection and dispatches incoming events. Event handlers
+are split by type:
 
 * `MessageEventHandlers/` — handle text messages. Each handler implements `IMessageEventHandler`, which requires:
-  * `CanHandle(message)`: returns `true` if this handler should process the given message.
-  * `Handle(message)`: extracts relevant information and invokes the corresponding command.
+    * `CanHandle(message)`: returns `true` if this handler should process the given message.
+    * `Handle(message)`: extracts relevant information and invokes the corresponding command.
 * `ReactionHandlers/` — handle emoji reactions (e.g. karma changes).
 * `MembershipEventHandlers/` — handle member join events.
 
 ### LlmBot
 
-Wraps [OllamaSharp](https://github.com/awaescher/OllamaSharp) to provide conversational AI responses via a locally-hosted Ollama instance.
+Wraps [OllamaSharp](https://github.com/awaescher/OllamaSharp) to provide conversational AI responses via a
+locally-hosted Ollama instance.
 
 ### Tests
 
@@ -63,15 +69,20 @@ Has an internal structure matching the rest of the app. Each app file should hav
 
 The test suite is split into two categories:
 
-* **Unit tests** — fast, in-process tests using [Moq](https://github.com/devlooped/moq) for mocking and [Shouldly](https://github.com/shouldly/shouldly) for assertions. Cover commands, event handlers, and other logic that can be exercised without external dependencies.
-* **Integration tests** (`Repositories/Integration/`) — use [Testcontainers](https://dotnet.testcontainers.org/) to spin up a real MongoDB container and exercise the repository layer end-to-end, including aggregation pipelines. These require Docker to be running locally; they run automatically in CI on `ubuntu-latest`.
+* **Unit tests** — fast, in-process tests using [Moq](https://github.com/devlooped/moq) for mocking
+  and [Shouldly](https://github.com/shouldly/shouldly) for assertions. Cover commands, event handlers, and other logic
+  that can be exercised without external dependencies.
+* **Integration tests** (`Repositories/Integration/`) — use [Testcontainers](https://dotnet.testcontainers.org/) to spin
+  up a real MongoDB container and exercise the repository layer end-to-end, including aggregation pipelines. These
+  require Docker to be running locally; they run automatically in CI on `ubuntu-latest`.
 
 ## Configuration
 
 The following secrets/environment variables _must_ be configured for the app to run:
 
 * `bottomly_env`: Describes the active environment. If not set to `live`, output messages will be marked as "DEBUG".
-* `bottomly_prefix`: The prefix for bot commands (e.g. `!`). Most commands require this prefix, allowing easy switching between test and production environments.
+* `bottomly_prefix`: The prefix for bot commands (e.g. `!`). Most commands require this prefix, allowing easy switching
+  between test and production environments.
 * `bottomly_slack_bot_token`: The Slack bot token (`xoxb-...`) for Socket Mode access.
 * `bottomly_slack_app_token`: The Slack app-level token (`xapp-...`) for Socket Mode.
 * `bottomly_google_api_key`: A valid Google API key.
@@ -79,8 +90,10 @@ The following secrets/environment variables _must_ be configured for the app to
 * `bottomly_giphy_api_key`: A valid Giphy API key.
 * `bottomly_github_token`: A GitHub personal access token.
 
-MongoDB and Ollama connection strings are managed automatically by Aspire in development. In production, configure them via standard .NET connection string settings.
+MongoDB and Ollama connection strings are managed automatically by Aspire in development. In production, configure them
+via standard .NET connection string settings.
 
 ## Contributing
 
-Most additions will involve adding a handler and command pair in the relevant modules, with the command delegating to the repository layer for any persistence work. PRs will *not be merged* without proper test coverage.
+Most additions will involve adding a handler and command pair in the relevant modules, with the command delegating to
+the repository layer for any persistence work. PRs will *not be merged* without proper test coverage.
diff --git a/bottomly.net.slnx b/bottomly.net.slnx
index d78ed50..f6ce000 100644
--- a/bottomly.net.slnx
+++ b/bottomly.net.slnx
@@ -1,17 +1,17 @@
 <Solution>
     <Folder Name="/GitHubWorkflows/">
-        <File Path=".azure/container-group.yml" />
-        <File Path=".github/workflows/dotnet.yml" />
-        <File Path=".github/workflows/push_to_live.yml" />
+        <File Path=".azure/container-group.yml"/>
+        <File Path=".github/workflows/dotnet.yml"/>
+        <File Path=".github/workflows/push_to_live.yml"/>
     </Folder>
     <Folder Name="/RepoConfig/">
-        <File Path=".editorconfig" />
-        <File Path=".gitignore" />
-        <File Path="NuGet.config" />
-        <File Path="README.md" />
+        <File Path=".editorconfig"/>
+        <File Path=".gitignore"/>
+        <File Path="NuGet.config"/>
+        <File Path="README.md"/>
     </Folder>
-    <Project Path="Bottomly.AppHost/Bottomly.AppHost.csproj" />
-    <Project Path="Bottomly.ServiceDefaults/Bottomly.ServiceDefaults.csproj" />
-    <Project Path="Bottomly.Tests/Bottomly.Tests.csproj" />
-    <Project Path="Bottomly/Bottomly.csproj" />
+    <Project Path="Bottomly.AppHost/Bottomly.AppHost.csproj"/>
+    <Project Path="Bottomly.ServiceDefaults/Bottomly.ServiceDefaults.csproj"/>
+    <Project Path="Bottomly.Tests/Bottomly.Tests.csproj"/>
+    <Project Path="Bottomly/Bottomly.csproj"/>
 </Solution>