diff --git a/src/GmRelay.Bot/Infrastructure/Health/BotHealthCheckHostedService.cs b/src/GmRelay.Bot/Infrastructure/Health/BotHealthCheckHostedService.cs
index 53bacc4..c14437c 100644
--- a/src/GmRelay.Bot/Infrastructure/Health/BotHealthCheckHostedService.cs
+++ b/src/GmRelay.Bot/Infrastructure/Health/BotHealthCheckHostedService.cs
@@ -72,10 +72,10 @@ public sealed class BotHealthCheckHostedService : IHostedService
 
     private async Task HandleRequestAsync(HttpListenerContext context)
     {
+        var response = context.Response;
         try
         {
             var request = context.Request;
-            var response = context.Response;
 
             if (request.Url?.AbsolutePath == "/health")
             {
@@ -88,12 +88,14 @@ public sealed class BotHealthCheckHostedService : IHostedService
             {
                 response.StatusCode = (int)HttpStatusCode.NotFound;
             }
-
-            response.Close();
         }
         catch (Exception ex)
         {
             _logger.LogError(ex, "Error handling health check request");
         }
+        finally
+        {
+            response.Close();
+        }
     }
 }
diff --git a/src/GmRelay.Web/Dockerfile b/src/GmRelay.Web/Dockerfile
index acdca55..970cd35 100644
--- a/src/GmRelay.Web/Dockerfile
+++ b/src/GmRelay.Web/Dockerfile
@@ -18,7 +18,7 @@ RUN dotnet publish "GmRelay.Web.csproj" -c Release -o /app/publish /p:UseAppHost
 # Stage 2: Runtime
 FROM mcr.microsoft.com/dotnet/aspnet:10.0-noble AS final
 WORKDIR /app
-RUN apt-get update && apt-get install -y --no-install-recommends libgssapi-krb5-2 && rm -rf /var/lib/apt/lists/*
+RUN apt-get update && apt-get install -y --no-install-recommends libgssapi-krb5-2 wget && rm -rf /var/lib/apt/lists/*
 COPY --from=build /app/publish .
 RUN mkdir -p /app/dataprotection-keys && chown -R $APP_UID:$APP_UID /app/dataprotection-keys
 ENV ASPNETCORE_URLS=http://+:8080
diff --git a/tests/GmRelay.Bot.Tests/Infrastructure/Health/BotHealthCheckHostedServiceTests.cs b/tests/GmRelay.Bot.Tests/Infrastructure/Health/BotHealthCheckHostedServiceTests.cs
index 601be7c..a30f9f8 100644
--- a/tests/GmRelay.Bot.Tests/Infrastructure/Health/BotHealthCheckHostedServiceTests.cs
+++ b/tests/GmRelay.Bot.Tests/Infrastructure/Health/BotHealthCheckHostedServiceTests.cs
@@ -1,4 +1,5 @@
 using System.Net;
+using System.Net.Sockets;
 using GmRelay.Bot.Infrastructure.Health;
 using Microsoft.Extensions.Configuration;
 using Microsoft.Extensions.Logging.Abstractions;
@@ -8,13 +9,15 @@ namespace GmRelay.Bot.Tests.Infrastructure.Health;
 public sealed class BotHealthCheckHostedServiceTests : IDisposable
 {
     private readonly BotHealthCheckHostedService _service;
+    private readonly int _port;
 
     public BotHealthCheckHostedServiceTests()
     {
+        _port = GetAvailablePort();
         var config = new ConfigurationBuilder()
             .AddInMemoryCollection(new Dictionary<string, string?>
             {
-                ["HealthCheck:Prefix"] = "http://localhost:8081/"
+                ["HealthCheck:Prefix"] = $"http://localhost:{_port}/"
             })
             .Build();
 
@@ -35,8 +38,17 @@ public sealed class BotHealthCheckHostedServiceTests : IDisposable
 
         using var client = new HttpClient();
         client.Timeout = TimeSpan.FromSeconds(5);
-        var response = await client.GetAsync("http://localhost:8081/health");
+        var response = await client.GetAsync($"http://localhost:{_port}/health");
 
         Assert.Equal(HttpStatusCode.OK, response.StatusCode);
     }
+
+    private static int GetAvailablePort()
+    {
+        var listener = new TcpListener(IPAddress.Loopback, 0);
+        listener.Start();
+        var port = ((IPEndPoint)listener.LocalEndpoint).Port;
+        listener.Stop();
+        return port;
+    }
 }
diff --git a/tests/GmRelay.Bot.Tests/Web/WebHealthEndpointTests.cs b/tests/GmRelay.Bot.Tests/Web/WebHealthEndpointTests.cs
index cb6efce..e165403 100644
--- a/tests/GmRelay.Bot.Tests/Web/WebHealthEndpointTests.cs
+++ b/tests/GmRelay.Bot.Tests/Web/WebHealthEndpointTests.cs
@@ -73,7 +73,7 @@ public sealed class WebHealthEndpointTests
     }
 
     [Fact]
-    public async Task NpgsqlHealthCheck_ShouldReturnHealthy_WhenDatabaseIsAccessible()
+    public async Task NpgsqlHealthCheck_ShouldReturnUnhealthy_WhenDatabaseIsInaccessible()
     {
         var dataSource = NpgsqlDataSource.Create("Host=localhost;Port=5432;Database=gmrelay_db;Username=gmrelay;Password=fake");
         var healthCheck = new NpgsqlHealthCheck(dataSource);