diff --git a/RoslynBridge/RoslynBridgePackage.cs b/RoslynBridge/RoslynBridgePackage.cs
index a0be444..ee1f300 100644
--- a/RoslynBridge/RoslynBridgePackage.cs
+++ b/RoslynBridge/RoslynBridgePackage.cs
@@ -18,6 +18,7 @@ namespace RoslynBridge
     {
         public const string PackageGuidString = "b2c3d4e5-f6a7-4b5c-9d8e-0f1a2b3c4d5e";
         private BridgeServer? _bridgeServer;
+        private Services.RegistrationService? _registrationService;
 
         protected override async Task InitializeAsync(CancellationToken cancellationToken, IProgress<ServiceProgressData> progress)
         {
@@ -29,6 +30,10 @@ namespace RoslynBridge
                 _bridgeServer = new BridgeServer(this);
                 await _bridgeServer.StartAsync();
 
+                // Register with WebAPI
+                _registrationService = new Services.RegistrationService(this, _bridgeServer.Port);
+                await _registrationService.RegisterAsync();
+
                 await base.InitializeAsync(cancellationToken, progress);
             }
             catch (Exception ex)
@@ -43,6 +48,8 @@ namespace RoslynBridge
         {
             if (disposing)
             {
+                _registrationService?.UnregisterAsync().Wait(TimeSpan.FromSeconds(5));
+                _registrationService?.Dispose();
                 _bridgeServer?.Dispose();
             }
             base.Dispose(disposing);
diff --git a/RoslynBridge/Services/RegistrationService.cs b/RoslynBridge/Services/RegistrationService.cs
new file mode 100644
index 0000000..a806b51
--- /dev/null
+++ b/RoslynBridge/Services/RegistrationService.cs
@@ -0,0 +1,138 @@
+using System;
+using System.Diagnostics;
+using System.Net.Http;
+using System.Text;
+using System.Text.Json;
+using System.Threading.Tasks;
+using Microsoft.VisualStudio.Shell;
+
+namespace RoslynBridge.Services
+{
+    /// <summary>
+    /// Service for registering this VS instance with the WebAPI
+    /// </summary>
+    public class RegistrationService : IDisposable
+    {
+        private readonly string _webApiUrl;
+        private readonly HttpClient _httpClient;
+        private readonly int _port;
+        private readonly AsyncPackage _package;
+        private System.Threading.Timer? _heartbeatTimer;
+        private bool _isRegistered;
+
+        public RegistrationService(AsyncPackage package, int port)
+        {
+            _package = package;
+            _port = port;
+            _webApiUrl = ConfigurationService.Instance.WebApiUrl;
+            _httpClient = new HttpClient { Timeout = TimeSpan.FromSeconds(5) };
+        }
+
+        public async Task RegisterAsync()
+        {
+            try
+            {
+                var dte = await GetDTEAsync();
+                var solutionPath = dte?.Solution?.FullName;
+                var solutionName = string.IsNullOrEmpty(solutionPath)
+                    ? null
+                    : System.IO.Path.GetFileNameWithoutExtension(solutionPath);
+
+                var registrationData = new
+                {
+                    port = _port,
+                    processId = Process.GetCurrentProcess().Id,
+                    solutionPath = string.IsNullOrEmpty(solutionPath) ? null : solutionPath,
+                    solutionName = solutionName,
+                    projects = new string[] { } // TODO: Get project names
+                };
+
+                var json = JsonSerializer.Serialize(registrationData);
+                var content = new StringContent(json, Encoding.UTF8, "application/json");
+
+                var response = await _httpClient.PostAsync($"{_webApiUrl}/api/instances/register", content);
+
+                if (response.IsSuccessStatusCode)
+                {
+                    _isRegistered = true;
+                    Debug.WriteLine($"Successfully registered with WebAPI at {_webApiUrl}");
+
+                    // Start heartbeat timer (configurable interval)
+                    var heartbeatInterval = TimeSpan.FromSeconds(ConfigurationService.Instance.HeartbeatIntervalSeconds);
+                    _heartbeatTimer = new System.Threading.Timer(
+                        async _ => await SendHeartbeatAsync(),
+                        null,
+                        heartbeatInterval,
+                        heartbeatInterval);
+                }
+                else
+                {
+                    Debug.WriteLine($"Failed to register with WebAPI: {response.StatusCode}");
+                }
+            }
+            catch (Exception ex)
+            {
+                Debug.WriteLine($"Error registering with WebAPI: {ex.Message}");
+                // Don't throw - registration is optional, VS extension should work standalone
+            }
+        }
+
+        private async Task SendHeartbeatAsync()
+        {
+            if (!_isRegistered)
+                return;
+
+            try
+            {
+                var processId = Process.GetCurrentProcess().Id;
+                var response = await _httpClient.PostAsync(
+                    $"{_webApiUrl}/api/instances/heartbeat/{processId}",
+                    null);
+
+                if (!response.IsSuccessStatusCode)
+                {
+                    Debug.WriteLine($"Heartbeat failed: {response.StatusCode}");
+                }
+            }
+            catch (Exception ex)
+            {
+                Debug.WriteLine($"Error sending heartbeat: {ex.Message}");
+            }
+        }
+
+        public async Task UnregisterAsync()
+        {
+            if (!_isRegistered)
+                return;
+
+            try
+            {
+                var processId = Process.GetCurrentProcess().Id;
+                var response = await _httpClient.PostAsync(
+                    $"{_webApiUrl}/api/instances/unregister/{processId}",
+                    null);
+
+                if (response.IsSuccessStatusCode)
+                {
+                    Debug.WriteLine("Successfully unregistered from WebAPI");
+                }
+            }
+            catch (Exception ex)
+            {
+                Debug.WriteLine($"Error unregistering from WebAPI: {ex.Message}");
+            }
+        }
+
+        private async Task<EnvDTE.DTE?> GetDTEAsync()
+        {
+            await ThreadHelper.JoinableTaskFactory.SwitchToMainThreadAsync();
+            return await _package.GetServiceAsync(typeof(EnvDTE.DTE)) as EnvDTE.DTE;
+        }
+
+        public void Dispose()
+        {
+            _heartbeatTimer?.Dispose();
+            _httpClient?.Dispose();
+        }
+    }
+}