diff --git a/pkg/server/README.md b/pkg/server/README.md
index 45342c9..6cd46b3 100644
--- a/pkg/server/README.md
+++ b/pkg/server/README.md
@@ -1,233 +1,314 @@
 # Server Package
 
-Graceful HTTP server with request draining and shutdown coordination.
+Production-ready HTTP server manager with graceful shutdown, request draining, and comprehensive TLS/HTTPS support.
+
+## Features
+
+✅ **Multiple Server Management** - Run multiple HTTP/HTTPS servers concurrently
+✅ **Graceful Shutdown** - Handles SIGINT/SIGTERM with request draining
+✅ **Automatic Request Rejection** - New requests get 503 during shutdown
+✅ **Health & Readiness Endpoints** - Kubernetes-ready health checks
+✅ **Shutdown Callbacks** - Register cleanup functions (DB, cache, metrics)
+✅ **Comprehensive TLS Support**:
+  - Certificate files (production)
+  - Self-signed certificates (development/testing)
+  - Let's Encrypt / AutoTLS (automatic certificate management)
+✅ **GZIP Compression** - Optional response compression
+✅ **Panic Recovery** - Automatic panic recovery middleware
+✅ **Configurable Timeouts** - Read, write, idle, drain, and shutdown timeouts
 
 ## Quick Start
 
+### Single Server
+
 ```go
 import "github.com/bitechdev/ResolveSpec/pkg/server"
 
-// Create server
-srv := server.NewGracefulServer(server.Config{
-    Addr:    ":8080",
-    Handler: router,
+// Create server manager
+mgr := server.NewManager()
+
+// Add server
+_, err := mgr.Add(server.Config{
+    Name:    "api-server",
+    Host:    "localhost",
+    Port:    8080,
+    Handler: myRouter,
+    GZIP:    true,
 })
 
-// Start server (blocks until shutdown signal)
-if err := srv.ListenAndServe(); err != nil {
+// Start and wait for shutdown signal
+if err := mgr.ServeWithGracefulShutdown(); err != nil {
     log.Fatal(err)
 }
 ```
 
-## Features
+### Multiple Servers
 
-✅ Graceful shutdown on SIGINT/SIGTERM
-✅ Request draining (waits for in-flight requests)
-✅ Automatic request rejection during shutdown
-✅ Health and readiness endpoints
-✅ Shutdown callbacks for cleanup
-✅ Configurable timeouts
+```go
+mgr := server.NewManager()
+
+// Public API
+mgr.Add(server.Config{
+    Name:    "public-api",
+    Port:    8080,
+    Handler: publicRouter,
+})
+
+// Admin API
+mgr.Add(server.Config{
+    Name:    "admin-api",
+    Port:    8081,
+    Handler: adminRouter,
+})
+
+// Start all and wait
+mgr.ServeWithGracefulShutdown()
+```
+
+## HTTPS/TLS Configuration
+
+### Option 1: Certificate Files (Production)
+
+```go
+mgr.Add(server.Config{
+    Name:    "https-server",
+    Host:    "0.0.0.0",
+    Port:    443,
+    Handler: handler,
+    SSLCert: "/etc/ssl/certs/server.crt",
+    SSLKey:  "/etc/ssl/private/server.key",
+})
+```
+
+### Option 2: Self-Signed Certificate (Development)
+
+```go
+mgr.Add(server.Config{
+    Name:          "dev-server",
+    Host:          "localhost",
+    Port:          8443,
+    Handler:       handler,
+    SelfSignedSSL: true,  // Auto-generates certificate
+})
+```
+
+### Option 3: Let's Encrypt / AutoTLS (Production)
+
+```go
+mgr.Add(server.Config{
+    Name:            "prod-server",
+    Host:            "0.0.0.0",
+    Port:            443,
+    Handler:         handler,
+    AutoTLS:         true,
+    AutoTLSDomains:  []string{"example.com", "www.example.com"},
+    AutoTLSEmail:    "admin@example.com",
+    AutoTLSCacheDir: "./certs-cache",  // Certificate cache directory
+})
+```
 
 ## Configuration
 
 ```go
-config := server.Config{
-    // Server address
-    Addr: ":8080",
+server.Config{
+    // Basic configuration
+    Name:        "my-server",        // Server name (required)
+    Host:        "0.0.0.0",          // Bind address
+    Port:        8080,               // Port (required)
+    Handler:     myRouter,           // HTTP handler (required)
+    Description: "My API server",    // Optional description
 
-    // HTTP handler
-    Handler: myRouter,
+    // Features
+    GZIP: true,                      // Enable GZIP compression
 
-    // Maximum time for graceful shutdown (default: 30s)
-    ShutdownTimeout: 30 * time.Second,
+    // TLS/HTTPS (choose one option)
+    SSLCert:         "/path/to/cert.pem",  // Certificate file
+    SSLKey:          "/path/to/key.pem",   // Key file
+    SelfSignedSSL:   false,                // Auto-generate self-signed cert
+    AutoTLS:         false,                // Let's Encrypt
+    AutoTLSDomains:  []string{},           // Domains for AutoTLS
+    AutoTLSEmail:    "",                   // Email for Let's Encrypt
+    AutoTLSCacheDir: "./certs-cache",      // Cert cache directory
 
-    // Time to wait for in-flight requests (default: 25s)
-    DrainTimeout: 25 * time.Second,
-
-    // Request read timeout (default: 10s)
-    ReadTimeout: 10 * time.Second,
-
-    // Response write timeout (default: 10s)
-    WriteTimeout: 10 * time.Second,
-
-    // Idle connection timeout (default: 120s)
-    IdleTimeout: 120 * time.Second,
+    // Timeouts
+    ShutdownTimeout: 30 * time.Second,     // Max shutdown time
+    DrainTimeout:    25 * time.Second,     // Request drain timeout
+    ReadTimeout:     15 * time.Second,     // Request read timeout
+    WriteTimeout:    15 * time.Second,     // Response write timeout
+    IdleTimeout:     60 * time.Second,     // Idle connection timeout
 }
-
-srv := server.NewGracefulServer(config)
 ```
 
-## Shutdown Behavior
+## Graceful Shutdown
 
-**Signal received (SIGINT/SIGTERM):**
+### Automatic (Recommended)
 
-1. **Mark as shutting down** - New requests get 503
-2. **Drain requests** - Wait up to `DrainTimeout` for in-flight requests
-3. **Shutdown server** - Close listeners and connections
-4. **Execute callbacks** - Run registered cleanup functions
+```go
+mgr := server.NewManager()
 
+// Add servers...
+
+// This blocks until SIGINT/SIGTERM
+mgr.ServeWithGracefulShutdown()
 ```
-Time   Event
-─────────────────────────────────────────
-0s     Signal received: SIGTERM
-       ├─ Mark as shutting down
-       ├─ Reject new requests (503)
-       └─ Start draining...
 
-1s     In-flight: 50 requests
-2s     In-flight: 32 requests
-3s     In-flight: 12 requests
-4s     In-flight: 3 requests
-5s     In-flight: 0 requests ✓
-       └─ All requests drained
+### Manual Control
 
-5s     Execute shutdown callbacks
-6s     Shutdown complete
+```go
+mgr := server.NewManager()
+
+// Add and start servers
+mgr.StartAll()
+
+// Later... stop gracefully
+ctx, cancel := context.WithTimeout(context.Background(), 30*time.Second)
+defer cancel()
+
+if err := mgr.StopAllWithContext(ctx); err != nil {
+    log.Printf("Shutdown error: %v", err)
+}
+```
+
+### Shutdown Callbacks
+
+Register cleanup functions to run during shutdown:
+
+```go
+// Close database
+mgr.RegisterShutdownCallback(func(ctx context.Context) error {
+    log.Println("Closing database...")
+    return db.Close()
+})
+
+// Flush metrics
+mgr.RegisterShutdownCallback(func(ctx context.Context) error {
+    log.Println("Flushing metrics...")
+    return metrics.Flush(ctx)
+})
+
+// Close cache
+mgr.RegisterShutdownCallback(func(ctx context.Context) error {
+    log.Println("Closing cache...")
+    return cache.Close()
+})
 ```
 
 ## Health Checks
 
-### Health Endpoint
-
-Returns 200 when healthy, 503 when shutting down:
+### Adding Health Endpoints
 
 ```go
-router.HandleFunc("/health", srv.HealthCheckHandler())
+instance, _ := mgr.Add(server.Config{
+    Name:    "api-server",
+    Port:    8080,
+    Handler: router,
+})
+
+// Add health endpoints to your router
+router.HandleFunc("/health", instance.HealthCheckHandler())
+router.HandleFunc("/ready", instance.ReadinessHandler())
 ```
 
-**Response (healthy):**
+### Health Endpoint
+
+Returns server health status:
+
+**Healthy (200 OK):**
 ```json
 {"status":"healthy"}
 ```
 
-**Response (shutting down):**
+**Shutting Down (503 Service Unavailable):**
 ```json
 {"status":"shutting_down"}
 ```
 
 ### Readiness Endpoint
 
-Includes in-flight request count:
+Returns readiness with in-flight request count:
 
-```go
-router.HandleFunc("/ready", srv.ReadinessHandler())
-```
-
-**Response:**
+**Ready (200 OK):**
 ```json
 {"ready":true,"in_flight_requests":12}
 ```
 
-**During shutdown:**
+**Not Ready (503 Service Unavailable):**
 ```json
 {"ready":false,"reason":"shutting_down"}
 ```
 
-## Shutdown Callbacks
+## Shutdown Behavior
 
-Register cleanup functions to run during shutdown:
+When a shutdown signal (SIGINT/SIGTERM) is received:
 
-```go
-// Close database
-server.RegisterShutdownCallback(func(ctx context.Context) error {
-    logger.Info("Closing database connection...")
-    return db.Close()
-})
+1. **Mark as shutting down** → New requests get 503
+2. **Execute callbacks** → Run cleanup functions
+3. **Drain requests** → Wait up to `DrainTimeout` for in-flight requests
+4. **Shutdown servers** → Close listeners and connections
 
-// Flush metrics
-server.RegisterShutdownCallback(func(ctx context.Context) error {
-    logger.Info("Flushing metrics...")
-    return metricsProvider.Flush(ctx)
-})
+```
+Time   Event
+─────────────────────────────────────────
+0s     Signal received: SIGTERM
+       ├─ Mark servers as shutting down
+       ├─ Reject new requests (503)
+       └─ Execute shutdown callbacks
 
-// Close cache
-server.RegisterShutdownCallback(func(ctx context.Context) error {
-    logger.Info("Closing cache...")
-    return cache.Close()
-})
+1s     Callbacks complete
+       └─ Start draining requests...
+
+2s     In-flight: 50 requests
+3s     In-flight: 32 requests
+4s     In-flight: 12 requests
+5s     In-flight: 3 requests
+6s     In-flight: 0 requests ✓
+       └─ All requests drained
+
+6s     Shutdown servers
+7s     All servers stopped ✓
 ```
 
-## Complete Example
+## Server Management
+
+### Get Server Instance
 
 ```go
-package main
-
-import (
-    "context"
-    "log"
-    "net/http"
-    "time"
-
-    "github.com/bitechdev/ResolveSpec/pkg/middleware"
-    "github.com/bitechdev/ResolveSpec/pkg/metrics"
-    "github.com/bitechdev/ResolveSpec/pkg/server"
-    "github.com/gorilla/mux"
-)
-
-func main() {
-    // Initialize metrics
-    metricsProvider := metrics.NewPrometheusProvider()
-    metrics.SetProvider(metricsProvider)
-
-    // Create router
-    router := mux.NewRouter()
-
-    // Apply middleware
-    rateLimiter := middleware.NewRateLimiter(100, 20)
-    sizeLimiter := middleware.NewRequestSizeLimiter(middleware.Size10MB)
-    sanitizer := middleware.DefaultSanitizer()
-
-    router.Use(rateLimiter.Middleware)
-    router.Use(sizeLimiter.Middleware)
-    router.Use(sanitizer.Middleware)
-    router.Use(metricsProvider.Middleware)
-
-    // API routes
-    router.HandleFunc("/api/data", dataHandler)
-
-    // Create graceful server
-    srv := server.NewGracefulServer(server.Config{
-        Addr:            ":8080",
-        Handler:         router,
-        ShutdownTimeout: 30 * time.Second,
-        DrainTimeout:    25 * time.Second,
-    })
-
-    // Health checks
-    router.HandleFunc("/health", srv.HealthCheckHandler())
-    router.HandleFunc("/ready", srv.ReadinessHandler())
-
-    // Metrics endpoint
-    router.Handle("/metrics", metricsProvider.Handler())
-
-    // Register shutdown callbacks
-    server.RegisterShutdownCallback(func(ctx context.Context) error {
-        log.Println("Cleanup: Flushing metrics...")
-        return nil
-    })
-
-    server.RegisterShutdownCallback(func(ctx context.Context) error {
-        log.Println("Cleanup: Closing database...")
-        // return db.Close()
-        return nil
-    })
-
-    // Start server (blocks until shutdown)
-    log.Printf("Starting server on :8080")
-    if err := srv.ListenAndServe(); err != nil {
-        log.Fatal(err)
-    }
-
-    // Wait for shutdown to complete
-    srv.Wait()
-    log.Println("Server stopped")
+instance, err := mgr.Get("api-server")
+if err != nil {
+    log.Fatal(err)
 }
 
-func dataHandler(w http.ResponseWriter, r *http.Request) {
-    // Your handler logic
-    time.Sleep(100 * time.Millisecond) // Simulate work
-    w.WriteHeader(http.StatusOK)
-    w.Write([]byte(`{"message":"success"}`))
+// Check status
+fmt.Printf("Address: %s\n", instance.Addr())
+fmt.Printf("Name: %s\n", instance.Name())
+fmt.Printf("In-flight: %d\n", instance.InFlightRequests())
+fmt.Printf("Shutting down: %v\n", instance.IsShuttingDown())
+```
+
+### List All Servers
+
+```go
+instances := mgr.List()
+for _, instance := range instances {
+    fmt.Printf("Server: %s at %s\n", instance.Name(), instance.Addr())
+}
+```
+
+### Remove Server
+
+```go
+// Stop and remove a server
+if err := mgr.Remove("api-server"); err != nil {
+    log.Printf("Error removing server: %v", err)
+}
+```
+
+### Restart All Servers
+
+```go
+// Gracefully restart all servers
+if err := mgr.RestartAll(); err != nil {
+    log.Printf("Error restarting: %v", err)
 }
 ```
 
@@ -250,23 +331,21 @@ spec:
         ports:
         - containerPort: 8080
 
-        # Liveness probe - is app running?
+        # Liveness probe
         livenessProbe:
           httpGet:
             path: /health
             port: 8080
           initialDelaySeconds: 10
           periodSeconds: 10
-          timeoutSeconds: 5
 
-        # Readiness probe - can app handle traffic?
+        # Readiness probe
         readinessProbe:
           httpGet:
             path: /ready
             port: 8080
           initialDelaySeconds: 5
           periodSeconds: 5
-          timeoutSeconds: 3
 
         # Graceful shutdown
         lifecycle:
@@ -274,26 +353,12 @@ spec:
             exec:
               command: ["/bin/sh", "-c", "sleep 5"]
 
-        # Environment
         env:
         - name: SHUTDOWN_TIMEOUT
           value: "30"
-```
 
-### Service
-
-```yaml
-apiVersion: v1
-kind: Service
-metadata:
-  name: myapp
-spec:
-  selector:
-    app: myapp
-  ports:
-  - port: 80
-    targetPort: 8080
-  type: LoadBalancer
+      # Allow time for graceful shutdown
+      terminationGracePeriodSeconds: 35
 ```
 
 ## Docker Compose
@@ -312,8 +377,70 @@ services:
       interval: 10s
       timeout: 5s
       retries: 3
-      start_period: 10s
-    stop_grace_period: 35s  # Slightly longer than shutdown timeout
+    stop_grace_period: 35s
+```
+
+## Complete Example
+
+```go
+package main
+
+import (
+    "context"
+    "log"
+    "net/http"
+    "time"
+
+    "github.com/bitechdev/ResolveSpec/pkg/server"
+)
+
+func main() {
+    // Create server manager
+    mgr := server.NewManager()
+
+    // Register shutdown callbacks
+    mgr.RegisterShutdownCallback(func(ctx context.Context) error {
+        log.Println("Cleanup: Closing database...")
+        // return db.Close()
+        return nil
+    })
+
+    // Create router
+    router := http.NewServeMux()
+    router.HandleFunc("/api/data", dataHandler)
+
+    // Add server
+    instance, err := mgr.Add(server.Config{
+        Name:            "api-server",
+        Host:            "0.0.0.0",
+        Port:            8080,
+        Handler:         router,
+        GZIP:            true,
+        ShutdownTimeout: 30 * time.Second,
+        DrainTimeout:    25 * time.Second,
+    })
+    if err != nil {
+        log.Fatal(err)
+    }
+
+    // Add health endpoints
+    router.HandleFunc("/health", instance.HealthCheckHandler())
+    router.HandleFunc("/ready", instance.ReadinessHandler())
+
+    // Start and wait for shutdown
+    log.Println("Starting server on :8080")
+    if err := mgr.ServeWithGracefulShutdown(); err != nil {
+        log.Printf("Server stopped: %v", err)
+    }
+
+    log.Println("Server shutdown complete")
+}
+
+func dataHandler(w http.ResponseWriter, r *http.Request) {
+    time.Sleep(100 * time.Millisecond) // Simulate work
+    w.WriteHeader(http.StatusOK)
+    w.Write([]byte(`{"message":"success"}`))
+}
 ```
 
 ## Testing Graceful Shutdown
@@ -330,7 +457,7 @@ SERVER_PID=$!
 # Wait for server to start
 sleep 2
 
-# Send some requests
+# Send requests
 for i in {1..10}; do
     curl http://localhost:8080/api/data &
 done
@@ -341,7 +468,7 @@ sleep 1
 # Send shutdown signal
 kill -TERM $SERVER_PID
 
-# Try to send more requests (should get 503)
+# Try more requests (should get 503)
 curl -v http://localhost:8080/api/data
 
 # Wait for server to stop
@@ -349,101 +476,13 @@ wait $SERVER_PID
 echo "Server stopped gracefully"
 ```
 
-### Expected Output
-
-```
-Starting server on :8080
-Received signal: terminated, initiating graceful shutdown
-Starting graceful shutdown...
-Waiting for 8 in-flight requests to complete...
-Waiting for 4 in-flight requests to complete...
-Waiting for 1 in-flight requests to complete...
-All requests drained in 2.3s
-Cleanup: Flushing metrics...
-Cleanup: Closing database...
-Shutting down HTTP server...
-Graceful shutdown complete
-Server stopped
-```
-
-## Monitoring In-Flight Requests
-
-```go
-// Get current in-flight count
-count := srv.InFlightRequests()
-fmt.Printf("In-flight requests: %d\n", count)
-
-// Check if shutting down
-if srv.IsShuttingDown() {
-    fmt.Println("Server is shutting down")
-}
-```
-
-## Advanced Usage
-
-### Custom Shutdown Logic
-
-```go
-// Implement custom shutdown
-go func() {
-    sigChan := make(chan os.Signal, 1)
-    signal.Notify(sigChan, os.Interrupt, syscall.SIGTERM)
-
-    <-sigChan
-    log.Println("Shutdown signal received")
-
-    // Custom pre-shutdown logic
-    log.Println("Running custom cleanup...")
-
-    // Shutdown with callbacks
-    ctx, cancel := context.WithTimeout(context.Background(), 30*time.Second)
-    defer cancel()
-
-    if err := srv.ShutdownWithCallbacks(ctx); err != nil {
-        log.Printf("Shutdown error: %v", err)
-    }
-}()
-
-// Start server
-srv.server.ListenAndServe()
-```
-
-### Multiple Servers
-
-```go
-// HTTP server
-httpSrv := server.NewGracefulServer(server.Config{
-    Addr:    ":8080",
-    Handler: httpRouter,
-})
-
-// HTTPS server
-httpsSrv := server.NewGracefulServer(server.Config{
-    Addr:    ":8443",
-    Handler: httpsRouter,
-})
-
-// Start both
-go httpSrv.ListenAndServe()
-go httpsSrv.ListenAndServe()
-
-// Shutdown both on signal
-sigChan := make(chan os.Signal, 1)
-signal.Notify(sigChan, os.Interrupt)
-<-sigChan
-
-ctx := context.Background()
-httpSrv.Shutdown(ctx)
-httpsSrv.Shutdown(ctx)
-```
-
 ## Best Practices
 
 1. **Set appropriate timeouts**
    - `DrainTimeout` < `ShutdownTimeout`
    - `ShutdownTimeout` < Kubernetes `terminationGracePeriodSeconds`
 
-2. **Register cleanup callbacks** for:
+2. **Use shutdown callbacks** for:
    - Database connections
    - Message queues
    - Metrics flushing
@@ -458,7 +497,12 @@ httpsSrv.Shutdown(ctx)
    - Set `preStop` hook in Kubernetes (5-10s delay)
    - Allows load balancer to deregister before shutdown
 
-5. **Monitoring**
+5. **HTTPS in production**
+   - Use AutoTLS for public-facing services
+   - Use certificate files for enterprise PKI
+   - Use self-signed only for development/testing
+
+6. **Monitoring**
    - Track in-flight requests in metrics
    - Alert on slow drains
    - Monitor shutdown duration
@@ -470,24 +514,63 @@ httpsSrv.Shutdown(ctx)
 ```go
 // Increase drain timeout
 config.DrainTimeout = 60 * time.Second
+config.ShutdownTimeout = 65 * time.Second
 ```
 
-### Requests Still Timing Out
+### Requests Timing Out
 
 ```go
 // Increase write timeout
 config.WriteTimeout = 30 * time.Second
 ```
 
-### Force Shutdown Not Working
-
-The server will force shutdown after `ShutdownTimeout` even if requests are still in-flight. Adjust timeouts as needed.
-
-### Debugging Shutdown
+### Certificate Issues
+
+```go
+// Verify certificate files exist and are readable
+if _, err := os.Stat(config.SSLCert); err != nil {
+    log.Fatalf("Certificate not found: %v", err)
+}
+
+// For AutoTLS, ensure:
+// - Port 443 is accessible
+// - Domains resolve to server IP
+// - Cache directory is writable
+```
+
+### Debug Logging
 
 ```go
-// Enable debug logging
 import "github.com/bitechdev/ResolveSpec/pkg/logger"
 
+// Enable debug logging
 logger.SetLevel("debug")
 ```
+
+## API Reference
+
+### Manager Methods
+
+- `NewManager()` - Create new server manager
+- `Add(cfg Config)` - Register server instance
+- `Get(name string)` - Get server by name
+- `Remove(name string)` - Stop and remove server
+- `StartAll()` - Start all registered servers
+- `StopAll()` - Stop all servers gracefully
+- `StopAllWithContext(ctx)` - Stop with timeout
+- `RestartAll()` - Restart all servers
+- `List()` - Get all server instances
+- `ServeWithGracefulShutdown()` - Start and block until shutdown
+- `RegisterShutdownCallback(cb)` - Register cleanup function
+
+### Instance Methods
+
+- `Start()` - Start the server
+- `Stop(ctx)` - Stop gracefully
+- `Addr()` - Get server address
+- `Name()` - Get server name
+- `HealthCheckHandler()` - Get health handler
+- `ReadinessHandler()` - Get readiness handler
+- `InFlightRequests()` - Get in-flight count
+- `IsShuttingDown()` - Check shutdown status
+- `Wait()` - Block until shutdown complete
diff --git a/pkg/server/example_test.go b/pkg/server/example_test.go
new file mode 100644
index 0000000..032b6f0
--- /dev/null
+++ b/pkg/server/example_test.go
@@ -0,0 +1,294 @@
+package server_test
+
+import (
+	"context"
+	"fmt"
+	"net/http"
+	"time"
+
+	"github.com/bitechdev/ResolveSpec/pkg/server"
+)
+
+// ExampleManager_basic demonstrates basic server manager usage
+func ExampleManager_basic() {
+	// Create a server manager
+	mgr := server.NewManager()
+
+	// Define a simple handler
+	handler := http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		w.WriteHeader(http.StatusOK)
+		fmt.Fprintln(w, "Hello from server!")
+	})
+
+	// Add an HTTP server
+	_, err := mgr.Add(server.Config{
+		Name:    "api-server",
+		Host:    "localhost",
+		Port:    8080,
+		Handler: handler,
+		GZIP:    true, // Enable GZIP compression
+	})
+	if err != nil {
+		panic(err)
+	}
+
+	// Start all servers
+	if err := mgr.StartAll(); err != nil {
+		panic(err)
+	}
+
+	// Server is now running...
+	// When done, stop gracefully
+	if err := mgr.StopAll(); err != nil {
+		panic(err)
+	}
+}
+
+// ExampleManager_https demonstrates HTTPS configurations
+func ExampleManager_https() {
+	mgr := server.NewManager()
+	handler := http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		fmt.Fprintln(w, "Secure connection!")
+	})
+
+	// Option 1: Use certificate files
+	_, err := mgr.Add(server.Config{
+		Name:    "https-server-files",
+		Host:    "localhost",
+		Port:    8443,
+		Handler: handler,
+		SSLCert: "/path/to/cert.pem",
+		SSLKey:  "/path/to/key.pem",
+	})
+	if err != nil {
+		panic(err)
+	}
+
+	// Option 2: Self-signed certificate (for development)
+	_, err = mgr.Add(server.Config{
+		Name:          "https-server-self-signed",
+		Host:          "localhost",
+		Port:          8444,
+		Handler:       handler,
+		SelfSignedSSL: true,
+	})
+	if err != nil {
+		panic(err)
+	}
+
+	// Option 3: Let's Encrypt / AutoTLS (for production)
+	_, err = mgr.Add(server.Config{
+		Name:           "https-server-letsencrypt",
+		Host:           "0.0.0.0",
+		Port:           443,
+		Handler:        handler,
+		AutoTLS:        true,
+		AutoTLSDomains: []string{"example.com", "www.example.com"},
+		AutoTLSEmail:   "admin@example.com",
+		AutoTLSCacheDir: "./certs-cache",
+	})
+	if err != nil {
+		panic(err)
+	}
+
+	// Start all servers
+	if err := mgr.StartAll(); err != nil {
+		panic(err)
+	}
+
+	// Cleanup
+	mgr.StopAll()
+}
+
+// ExampleManager_gracefulShutdown demonstrates graceful shutdown with callbacks
+func ExampleManager_gracefulShutdown() {
+	mgr := server.NewManager()
+
+	// Register shutdown callbacks for cleanup tasks
+	mgr.RegisterShutdownCallback(func(ctx context.Context) error {
+		fmt.Println("Closing database connections...")
+		// Close your database here
+		return nil
+	})
+
+	mgr.RegisterShutdownCallback(func(ctx context.Context) error {
+		fmt.Println("Flushing metrics...")
+		// Flush metrics here
+		return nil
+	})
+
+	// Add server with custom timeouts
+	handler := http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		// Simulate some work
+		time.Sleep(100 * time.Millisecond)
+		fmt.Fprintln(w, "Done!")
+	})
+
+	_, err := mgr.Add(server.Config{
+		Name:            "api-server",
+		Host:            "localhost",
+		Port:            8080,
+		Handler:         handler,
+		ShutdownTimeout: 30 * time.Second, // Max time for shutdown
+		DrainTimeout:    25 * time.Second, // Time to wait for in-flight requests
+		ReadTimeout:     10 * time.Second,
+		WriteTimeout:    10 * time.Second,
+		IdleTimeout:     120 * time.Second,
+	})
+	if err != nil {
+		panic(err)
+	}
+
+	// Start servers and block until shutdown signal (SIGINT/SIGTERM)
+	// This will automatically handle graceful shutdown with callbacks
+	if err := mgr.ServeWithGracefulShutdown(); err != nil {
+		fmt.Printf("Shutdown completed: %v\n", err)
+	}
+}
+
+// ExampleManager_healthChecks demonstrates health and readiness endpoints
+func ExampleManager_healthChecks() {
+	mgr := server.NewManager()
+
+	// Create a router with health endpoints
+	mux := http.NewServeMux()
+	mux.HandleFunc("/api/data", func(w http.ResponseWriter, r *http.Request) {
+		fmt.Fprintln(w, "Data endpoint")
+	})
+
+	// Add server
+	instance, err := mgr.Add(server.Config{
+		Name:    "api-server",
+		Host:    "localhost",
+		Port:    8080,
+		Handler: mux,
+	})
+	if err != nil {
+		panic(err)
+	}
+
+	// Add health and readiness endpoints
+	mux.HandleFunc("/health", instance.HealthCheckHandler())
+	mux.HandleFunc("/ready", instance.ReadinessHandler())
+
+	// Start the server
+	if err := mgr.StartAll(); err != nil {
+		panic(err)
+	}
+
+	// Health check returns:
+	// - 200 OK with {"status":"healthy"} when healthy
+	// - 503 Service Unavailable with {"status":"shutting_down"} when shutting down
+
+	// Readiness check returns:
+	// - 200 OK with {"ready":true,"in_flight_requests":N} when ready
+	// - 503 Service Unavailable with {"ready":false,"reason":"shutting_down"} when shutting down
+
+	// Cleanup
+	mgr.StopAll()
+}
+
+// ExampleManager_multipleServers demonstrates running multiple servers
+func ExampleManager_multipleServers() {
+	mgr := server.NewManager()
+
+	// Public API server
+	publicHandler := http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		fmt.Fprintln(w, "Public API")
+	})
+	_, err := mgr.Add(server.Config{
+		Name:    "public-api",
+		Host:    "0.0.0.0",
+		Port:    8080,
+		Handler: publicHandler,
+		GZIP:    true,
+	})
+	if err != nil {
+		panic(err)
+	}
+
+	// Admin API server (different port)
+	adminHandler := http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		fmt.Fprintln(w, "Admin API")
+	})
+	_, err = mgr.Add(server.Config{
+		Name:    "admin-api",
+		Host:    "localhost",
+		Port:    8081,
+		Handler: adminHandler,
+	})
+	if err != nil {
+		panic(err)
+	}
+
+	// Metrics server (internal only)
+	metricsHandler := http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		fmt.Fprintln(w, "Metrics data")
+	})
+	_, err = mgr.Add(server.Config{
+		Name:    "metrics",
+		Host:    "127.0.0.1",
+		Port:    9090,
+		Handler: metricsHandler,
+	})
+	if err != nil {
+		panic(err)
+	}
+
+	// Start all servers at once
+	if err := mgr.StartAll(); err != nil {
+		panic(err)
+	}
+
+	// Get specific server instance
+	publicInstance, err := mgr.Get("public-api")
+	if err != nil {
+		panic(err)
+	}
+	fmt.Printf("Public API running on: %s\n", publicInstance.Addr())
+
+	// List all servers
+	instances := mgr.List()
+	fmt.Printf("Running %d servers\n", len(instances))
+
+	// Stop all servers gracefully (in parallel)
+	if err := mgr.StopAll(); err != nil {
+		panic(err)
+	}
+}
+
+// ExampleManager_monitoring demonstrates monitoring server state
+func ExampleManager_monitoring() {
+	mgr := server.NewManager()
+
+	handler := http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		time.Sleep(50 * time.Millisecond) // Simulate work
+		fmt.Fprintln(w, "Done")
+	})
+
+	instance, err := mgr.Add(server.Config{
+		Name:    "api-server",
+		Host:    "localhost",
+		Port:    8080,
+		Handler: handler,
+	})
+	if err != nil {
+		panic(err)
+	}
+
+	if err := mgr.StartAll(); err != nil {
+		panic(err)
+	}
+
+	// Check server status
+	fmt.Printf("Server address: %s\n", instance.Addr())
+	fmt.Printf("Server name: %s\n", instance.Name())
+	fmt.Printf("Is shutting down: %v\n", instance.IsShuttingDown())
+	fmt.Printf("In-flight requests: %d\n", instance.InFlightRequests())
+
+	// Cleanup
+	mgr.StopAll()
+
+	// Wait for complete shutdown
+	instance.Wait()
+}
diff --git a/pkg/server/interfaces.go b/pkg/server/interfaces.go
index 892cb58..633c394 100644
--- a/pkg/server/interfaces.go
+++ b/pkg/server/interfaces.go
@@ -3,6 +3,7 @@ package server
 import (
 	"context"
 	"net/http"
+	"time"
 )
 
 // Config holds the configuration for a single web server instance.
@@ -11,11 +12,52 @@ type Config struct {
 	Host        string
 	Port        int
 	Description string
-	SSLCert     string
-	SSLKey      string
-	GZIP        bool
+
 	// Handler is the http.Handler (e.g., a router) to be served.
 	Handler http.Handler
+
+	// GZIP compression support
+	GZIP bool
+
+	// TLS/HTTPS configuration options (mutually exclusive)
+	// Option 1: Provide certificate and key files directly
+	SSLCert string
+	SSLKey  string
+
+	// Option 2: Use self-signed certificate (for development/testing)
+	// Generates a self-signed certificate automatically if no SSLCert/SSLKey provided
+	SelfSignedSSL bool
+
+	// Option 3: Use Let's Encrypt / Certbot for automatic TLS
+	// AutoTLS enables automatic certificate management via Let's Encrypt
+	AutoTLS bool
+	// AutoTLSDomains specifies the domains for Let's Encrypt certificates
+	AutoTLSDomains []string
+	// AutoTLSCacheDir specifies where to cache certificates (default: "./certs-cache")
+	AutoTLSCacheDir string
+	// AutoTLSEmail is the email for Let's Encrypt registration (optional but recommended)
+	AutoTLSEmail string
+
+	// Graceful shutdown configuration
+	// ShutdownTimeout is the maximum time to wait for graceful shutdown
+	// Default: 30 seconds
+	ShutdownTimeout time.Duration
+
+	// DrainTimeout is the time to wait for in-flight requests to complete
+	// before forcing shutdown. Default: 25 seconds
+	DrainTimeout time.Duration
+
+	// ReadTimeout is the maximum duration for reading the entire request
+	// Default: 15 seconds
+	ReadTimeout time.Duration
+
+	// WriteTimeout is the maximum duration before timing out writes of the response
+	// Default: 15 seconds
+	WriteTimeout time.Duration
+
+	// IdleTimeout is the maximum amount of time to wait for the next request
+	// Default: 60 seconds
+	IdleTimeout time.Duration
 }
 
 // Instance defines the interface for a single server instance.
@@ -24,11 +66,33 @@ type Instance interface {
 	// Start begins serving requests. This method should be non-blocking and
 	// run the server in a separate goroutine.
 	Start() error
+
 	// Stop gracefully shuts down the server without interrupting any active connections.
 	// It accepts a context to allow for a timeout.
 	Stop(ctx context.Context) error
+
 	// Addr returns the network address the server is listening on.
 	Addr() string
+
+	// Name returns the server instance name.
+	Name() string
+
+	// HealthCheckHandler returns a handler that responds to health checks.
+	// Returns 200 OK when healthy, 503 Service Unavailable when shutting down.
+	HealthCheckHandler() http.HandlerFunc
+
+	// ReadinessHandler returns a handler for readiness checks.
+	// Includes in-flight request count.
+	ReadinessHandler() http.HandlerFunc
+
+	// InFlightRequests returns the current number of in-flight requests.
+	InFlightRequests() int64
+
+	// IsShuttingDown returns true if the server is shutting down.
+	IsShuttingDown() bool
+
+	// Wait blocks until shutdown is complete.
+	Wait()
 }
 
 // Manager defines the interface for a server manager.
@@ -37,16 +101,37 @@ type Manager interface {
 	// Add registers a new server instance based on the provided configuration.
 	// The server is not started until StartAll or Start is called on the instance.
 	Add(cfg Config) (Instance, error)
+
 	// Get returns a server instance by its name.
 	Get(name string) (Instance, error)
+
 	// Remove stops and removes a server instance by its name.
 	Remove(name string) error
+
 	// StartAll starts all registered server instances that are not already running.
 	StartAll() error
+
 	// StopAll gracefully shuts down all running server instances.
+	// Executes shutdown callbacks and drains in-flight requests.
 	StopAll() error
+
+	// StopAllWithContext gracefully shuts down all running server instances with a context.
+	StopAllWithContext(ctx context.Context) error
+
 	// RestartAll gracefully restarts all running server instances.
 	RestartAll() error
+
 	// List returns all registered server instances.
 	List() []Instance
+
+	// ServeWithGracefulShutdown starts all servers and blocks until a shutdown signal is received.
+	// It handles SIGINT and SIGTERM signals and performs graceful shutdown with callbacks.
+	ServeWithGracefulShutdown() error
+
+	// RegisterShutdownCallback registers a callback to be called during shutdown.
+	// Useful for cleanup tasks like closing database connections, flushing metrics, etc.
+	RegisterShutdownCallback(cb ShutdownCallback)
 }
+
+// ShutdownCallback is a function called during graceful shutdown.
+type ShutdownCallback func(context.Context) error
diff --git a/pkg/server/manager.go b/pkg/server/manager.go
index 005d8fa..02f0c3a 100644
--- a/pkg/server/manager.go
+++ b/pkg/server/manager.go
@@ -4,26 +4,173 @@ import (
 	"context"
 	"crypto/tls"
 	"fmt"
+	"net"
 	"net/http"
+	"os"
+	"os/signal"
 	"sync"
+	"sync/atomic"
+	"syscall"
 	"time"
 
 	"github.com/bitechdev/ResolveSpec/pkg/logger"
 	"github.com/bitechdev/ResolveSpec/pkg/middleware"
 	"github.com/klauspost/compress/gzhttp"
-	"golang.org/x/net/http2"
 )
 
-// serverManager manages a collection of server instances.
+// gracefulServer wraps http.Server with graceful shutdown capabilities (internal type)
+type gracefulServer struct {
+	server           *http.Server
+	shutdownTimeout  time.Duration
+	drainTimeout     time.Duration
+	inFlightRequests atomic.Int64
+	isShuttingDown   atomic.Bool
+	shutdownOnce     sync.Once
+	shutdownComplete chan struct{}
+}
+
+// trackRequestsMiddleware tracks in-flight requests and blocks new requests during shutdown
+func (gs *gracefulServer) trackRequestsMiddleware(next http.Handler) http.Handler {
+	return http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		// Check if shutting down
+		if gs.isShuttingDown.Load() {
+			http.Error(w, `{"error":"service_unavailable","message":"Server is shutting down"}`, http.StatusServiceUnavailable)
+			return
+		}
+
+		// Increment in-flight counter
+		gs.inFlightRequests.Add(1)
+		defer gs.inFlightRequests.Add(-1)
+
+		// Serve the request
+		next.ServeHTTP(w, r)
+	})
+}
+
+// shutdown performs graceful shutdown with request draining
+func (gs *gracefulServer) shutdown(ctx context.Context) error {
+	var shutdownErr error
+
+	gs.shutdownOnce.Do(func() {
+		logger.Info("Starting graceful shutdown...")
+
+		// Mark as shutting down (new requests will be rejected)
+		gs.isShuttingDown.Store(true)
+
+		// Create context with timeout
+		shutdownCtx, cancel := context.WithTimeout(ctx, gs.shutdownTimeout)
+		defer cancel()
+
+		// Wait for in-flight requests to complete (with drain timeout)
+		drainCtx, drainCancel := context.WithTimeout(shutdownCtx, gs.drainTimeout)
+		defer drainCancel()
+
+		shutdownErr = gs.drainRequests(drainCtx)
+		if shutdownErr != nil {
+			logger.Error("Error draining requests: %v", shutdownErr)
+		}
+
+		// Shutdown the server
+		logger.Info("Shutting down HTTP server...")
+		if err := gs.server.Shutdown(shutdownCtx); err != nil {
+			logger.Error("Error shutting down server: %v", err)
+			if shutdownErr == nil {
+				shutdownErr = err
+			}
+		}
+
+		logger.Info("Graceful shutdown complete")
+		close(gs.shutdownComplete)
+	})
+
+	return shutdownErr
+}
+
+// drainRequests waits for in-flight requests to complete
+func (gs *gracefulServer) drainRequests(ctx context.Context) error {
+	ticker := time.NewTicker(100 * time.Millisecond)
+	defer ticker.Stop()
+
+	startTime := time.Now()
+
+	for {
+		inFlight := gs.inFlightRequests.Load()
+
+		if inFlight == 0 {
+			logger.Info("All requests drained in %v", time.Since(startTime))
+			return nil
+		}
+
+		select {
+		case <-ctx.Done():
+			logger.Warn("Drain timeout exceeded with %d requests still in flight", inFlight)
+			return fmt.Errorf("drain timeout exceeded: %d requests still in flight", inFlight)
+		case <-ticker.C:
+			logger.Debug("Waiting for %d in-flight requests to complete...", inFlight)
+		}
+	}
+}
+
+// inFlightRequests returns the current number of in-flight requests
+func (gs *gracefulServer) inFlightRequestsCount() int64 {
+	return gs.inFlightRequests.Load()
+}
+
+// isShutdown returns true if the server is shutting down
+func (gs *gracefulServer) isShutdown() bool {
+	return gs.isShuttingDown.Load()
+}
+
+// wait blocks until shutdown is complete
+func (gs *gracefulServer) wait() {
+	<-gs.shutdownComplete
+}
+
+// healthCheckHandler returns a handler that responds to health checks
+func (gs *gracefulServer) healthCheckHandler() http.HandlerFunc {
+	return func(w http.ResponseWriter, r *http.Request) {
+		if gs.isShutdown() {
+			http.Error(w, `{"status":"shutting_down"}`, http.StatusServiceUnavailable)
+			return
+		}
+
+		w.Header().Set("Content-Type", "application/json")
+		w.WriteHeader(http.StatusOK)
+		_, err := w.Write([]byte(`{"status":"healthy"}`))
+		if err != nil {
+			logger.Warn("Failed to write health check response: %v", err)
+		}
+	}
+}
+
+// readinessHandler returns a handler for readiness checks
+func (gs *gracefulServer) readinessHandler() http.HandlerFunc {
+	return func(w http.ResponseWriter, r *http.Request) {
+		if gs.isShutdown() {
+			http.Error(w, `{"ready":false,"reason":"shutting_down"}`, http.StatusServiceUnavailable)
+			return
+		}
+
+		inFlight := gs.inFlightRequestsCount()
+		w.Header().Set("Content-Type", "application/json")
+		w.WriteHeader(http.StatusOK)
+		fmt.Fprintf(w, `{"ready":true,"in_flight_requests":%d}`, inFlight)
+	}
+}
+
+// serverManager manages a collection of server instances with graceful shutdown support.
 type serverManager struct {
-	instances map[string]Instance
-	mu        sync.RWMutex
+	instances         map[string]Instance
+	mu                sync.RWMutex
+	shutdownCallbacks []ShutdownCallback
+	callbacksMu       sync.Mutex
 }
 
 // NewManager creates a new server manager.
 func NewManager() Manager {
 	return &serverManager{
-		instances: make(map[string]Instance),
+		instances:         make(map[string]Instance),
+		shutdownCallbacks: make([]ShutdownCallback, 0),
 	}
 }
 
@@ -74,7 +221,7 @@ func (sm *serverManager) Remove(name string) error {
 	ctx, cancel := context.WithTimeout(context.Background(), 10*time.Second)
 	defer cancel()
 	if err := instance.Stop(ctx); err != nil {
-		logger.Warn("Failed to gracefully stop server '%s' on remove: %v", name, err, context.Background())
+		logger.Warn("Failed to gracefully stop server '%s' on remove: %v", name, err)
 	}
 
 	delete(sm.instances, name)
@@ -94,7 +241,6 @@ func (sm *serverManager) StartAll() error {
 	}
 
 	if len(startErrors) > 0 {
-		// In a real-world scenario, you might want a more sophisticated error handling strategy
 		return fmt.Errorf("encountered errors while starting servers: %v", startErrors)
 	}
 	return nil
@@ -102,6 +248,11 @@ func (sm *serverManager) StartAll() error {
 
 // StopAll gracefully shuts down all running server instances.
 func (sm *serverManager) StopAll() error {
+	return sm.StopAllWithContext(context.Background())
+}
+
+// StopAllWithContext gracefully shuts down all running server instances with a context.
+func (sm *serverManager) StopAllWithContext(ctx context.Context) error {
 	sm.mu.RLock()
 	instancesToStop := make([]Instance, 0, len(sm.instances))
 	for _, instance := range sm.instances {
@@ -109,19 +260,38 @@ func (sm *serverManager) StopAll() error {
 	}
 	sm.mu.RUnlock()
 
-	logger.Info("Shutting down all servers...", context.Background())
+	logger.Info("Shutting down all servers...")
 
+	// Execute shutdown callbacks first
+	sm.callbacksMu.Lock()
+	callbacks := make([]ShutdownCallback, len(sm.shutdownCallbacks))
+	copy(callbacks, sm.shutdownCallbacks)
+	sm.callbacksMu.Unlock()
+
+	if len(callbacks) > 0 {
+		logger.Info("Executing %d shutdown callbacks...", len(callbacks))
+		for i, cb := range callbacks {
+			if err := cb(ctx); err != nil {
+				logger.Error("Shutdown callback %d failed: %v", i+1, err)
+			}
+		}
+	}
+
+	// Stop all instances in parallel
 	var shutdownErrors []error
 	var wg sync.WaitGroup
+	var errorsMu sync.Mutex
 
 	for _, instance := range instancesToStop {
 		wg.Add(1)
 		go func(inst Instance) {
 			defer wg.Done()
-			ctx, cancel := context.WithTimeout(context.Background(), 15*time.Second)
+			shutdownCtx, cancel := context.WithTimeout(ctx, 15*time.Second)
 			defer cancel()
-			if err := inst.Stop(ctx); err != nil {
-				shutdownErrors = append(shutdownErrors, fmt.Errorf("failed to stop server '%s': %w", inst.Addr(), err))
+			if err := inst.Stop(shutdownCtx); err != nil {
+				errorsMu.Lock()
+				shutdownErrors = append(shutdownErrors, fmt.Errorf("failed to stop server '%s': %w", inst.Name(), err))
+				errorsMu.Unlock()
 			}
 		}(instance)
 	}
@@ -131,13 +301,13 @@ func (sm *serverManager) StopAll() error {
 	if len(shutdownErrors) > 0 {
 		return fmt.Errorf("encountered errors while stopping servers: %v", shutdownErrors)
 	}
-	logger.Info("All servers stopped gracefully.", context.Background())
+	logger.Info("All servers stopped gracefully.")
 	return nil
 }
 
 // RestartAll gracefully restarts all running server instances.
 func (sm *serverManager) RestartAll() error {
-	logger.Info("Restarting all servers...", context.Background())
+	logger.Info("Restarting all servers...")
 	if err := sm.StopAll(); err != nil {
 		return fmt.Errorf("failed to stop servers during restart: %w", err)
 	}
@@ -148,7 +318,7 @@ func (sm *serverManager) RestartAll() error {
 	if err := sm.StartAll(); err != nil {
 		return fmt.Errorf("failed to start servers during restart: %w", err)
 	}
-	logger.Info("All servers restarted successfully.", context.Background())
+	logger.Info("All servers restarted successfully.")
 	return nil
 }
 
@@ -164,13 +334,46 @@ func (sm *serverManager) List() []Instance {
 	return instances
 }
 
+// RegisterShutdownCallback registers a callback to be called during shutdown.
+func (sm *serverManager) RegisterShutdownCallback(cb ShutdownCallback) {
+	sm.callbacksMu.Lock()
+	defer sm.callbacksMu.Unlock()
+	sm.shutdownCallbacks = append(sm.shutdownCallbacks, cb)
+}
+
+// ServeWithGracefulShutdown starts all servers and blocks until a shutdown signal is received.
+func (sm *serverManager) ServeWithGracefulShutdown() error {
+	// Start all servers
+	if err := sm.StartAll(); err != nil {
+		return fmt.Errorf("failed to start servers: %w", err)
+	}
+
+	logger.Info("All servers started. Waiting for shutdown signal...")
+
+	// Wait for interrupt signal
+	sigChan := make(chan os.Signal, 1)
+	signal.Notify(sigChan, os.Interrupt, syscall.SIGTERM, syscall.SIGINT)
+
+	sig := <-sigChan
+	logger.Info("Received signal: %v, initiating graceful shutdown", sig)
+
+	// Create context with timeout for shutdown
+	ctx, cancel := context.WithTimeout(context.Background(), 30*time.Second)
+	defer cancel()
+
+	return sm.StopAllWithContext(ctx)
+}
+
 // serverInstance is a concrete implementation of the Instance interface.
+// It wraps gracefulServer to provide graceful shutdown capabilities.
 type serverInstance struct {
-	cfg        Config
-	httpServer *http.Server
-	mu         sync.RWMutex
-	running    bool
-	stopCh     chan struct{}
+	cfg            Config
+	gracefulServer *gracefulServer
+	certFile       string // Path to certificate file (may be temporary for self-signed)
+	keyFile        string // Path to key file (may be temporary for self-signed)
+	mu             sync.RWMutex
+	running        bool
+	serverErr      chan error
 }
 
 // newInstance creates a new, unstarted server instance from a config.
@@ -179,12 +382,29 @@ func newInstance(cfg Config) (*serverInstance, error) {
 		return nil, fmt.Errorf("handler cannot be nil")
 	}
 
+	// Set default timeouts
+	if cfg.ShutdownTimeout == 0 {
+		cfg.ShutdownTimeout = 30 * time.Second
+	}
+	if cfg.DrainTimeout == 0 {
+		cfg.DrainTimeout = 25 * time.Second
+	}
+	if cfg.ReadTimeout == 0 {
+		cfg.ReadTimeout = 15 * time.Second
+	}
+	if cfg.WriteTimeout == 0 {
+		cfg.WriteTimeout = 15 * time.Second
+	}
+	if cfg.IdleTimeout == 0 {
+		cfg.IdleTimeout = 60 * time.Second
+	}
+
 	addr := fmt.Sprintf("%s:%d", cfg.Host, cfg.Port)
 	var handler http.Handler = cfg.Handler
 
 	// Wrap with GZIP handler if enabled
 	if cfg.GZIP {
-		gz, err := gzhttp.NewWrapper(gzhttp.BestSpeed)
+		gz, err := gzhttp.NewWrapper()
 		if err != nil {
 			return nil, fmt.Errorf("failed to create GZIP wrapper: %w", err)
 		}
@@ -194,20 +414,33 @@ func newInstance(cfg Config) (*serverInstance, error) {
 	// Wrap with the panic recovery middleware
 	handler = middleware.PanicRecovery(handler)
 
-	// Here you could add other default middleware like request logging, metrics, etc.
+	// Configure TLS if any TLS option is enabled
+	tlsConfig, certFile, keyFile, err := configureTLS(cfg)
+	if err != nil {
+		return nil, fmt.Errorf("failed to configure TLS: %w", err)
+	}
 
-	httpServer := &http.Server{
-		Addr:         addr,
-		Handler:      handler,
-		ReadTimeout:  15 * time.Second,
-		WriteTimeout: 15 * time.Second,
-		IdleTimeout:  60 * time.Second,
+	// Create gracefulServer
+	gracefulSrv := &gracefulServer{
+		server: &http.Server{
+			Addr:         addr,
+			Handler:      handler,
+			ReadTimeout:  cfg.ReadTimeout,
+			WriteTimeout: cfg.WriteTimeout,
+			IdleTimeout:  cfg.IdleTimeout,
+			TLSConfig:    tlsConfig,
+		},
+		shutdownTimeout:  cfg.ShutdownTimeout,
+		drainTimeout:     cfg.DrainTimeout,
+		shutdownComplete: make(chan struct{}),
 	}
 
 	return &serverInstance{
-		cfg:        cfg,
-		httpServer: httpServer,
-		stopCh:     make(chan struct{}),
+		cfg:            cfg,
+		gracefulServer: gracefulSrv,
+		certFile:       certFile,
+		keyFile:        keyFile,
+		serverErr:      make(chan error, 1),
 	}, nil
 }
 
@@ -220,42 +453,69 @@ func (s *serverInstance) Start() error {
 		return fmt.Errorf("server '%s' is already running", s.cfg.Name)
 	}
 
-	hasSSL := s.cfg.SSLCert != "" && s.cfg.SSLKey != ""
+	// Determine if we're using TLS
+	useTLS := s.cfg.SSLCert != "" || s.cfg.SSLKey != "" || s.cfg.SelfSignedSSL || s.cfg.AutoTLS
+
+	// Wrap handler with request tracking
+	s.gracefulServer.server.Handler = s.gracefulServer.trackRequestsMiddleware(s.gracefulServer.server.Handler)
 
 	go func() {
 		defer func() {
 			s.mu.Lock()
 			s.running = false
 			s.mu.Unlock()
-			logger.Info("Server '%s' stopped.", s.cfg.Name, context.Background())
+			logger.Info("Server '%s' stopped.", s.cfg.Name)
 		}()
 
 		var err error
 		protocol := "HTTP"
 
-		if hasSSL {
+		if useTLS {
 			protocol = "HTTPS"
-			// Configure TLS + HTTP/2
-			s.httpServer.TLSConfig = &tls.Config{
-				MinVersion: tls.VersionTLS12,
+			logger.Info("Starting %s server '%s' on %s", protocol, s.cfg.Name, s.Addr())
+
+			// For AutoTLS, we need to use a TLS listener
+			if s.cfg.AutoTLS {
+				// Create listener
+				ln, lnErr := net.Listen("tcp", s.gracefulServer.server.Addr)
+				if lnErr != nil {
+					err = fmt.Errorf("failed to create listener: %w", lnErr)
+				} else {
+					// Wrap with TLS
+					tlsListener := tls.NewListener(ln, s.gracefulServer.server.TLSConfig)
+					err = s.gracefulServer.server.Serve(tlsListener)
+				}
+			} else {
+				// Use certificate files (regular SSL or self-signed)
+				err = s.gracefulServer.server.ListenAndServeTLS(s.certFile, s.keyFile)
 			}
-			            logger.Info("Starting %s server '%s' on %s", protocol, s.cfg.Name, s.Addr(), context.Background())			err = s.httpServer.ListenAndServeTLS(s.cfg.SSLCert, s.cfg.SSLKey)
 		} else {
-			logger.Info("Starting %s server '%s' on %s", protocol, s.cfg.Name, s.Addr(), context.Background())
-			err = s.httpServer.ListenAndServe()
+			logger.Info("Starting %s server '%s' on %s", protocol, s.cfg.Name, s.Addr())
+			err = s.gracefulServer.server.ListenAndServe()
 		}
 
-		// If the server stopped for a reason other than a graceful shutdown, log the error.
+		// If the server stopped for a reason other than a graceful shutdown, log and report the error.
 		if err != nil && err != http.ErrServerClosed {
-			logger.Error("Server '%s' failed: %v", s.cfg.Name, err, context.Background())
+			logger.Error("Server '%s' failed: %v", s.cfg.Name, err)
+			select {
+			case s.serverErr <- err:
+			default:
+			}
 		}
 	}()
 
 	s.running = true
 	// A small delay to allow the goroutine to start and potentially fail on binding.
-	// A more robust solution might involve a channel signal.
 	time.Sleep(50 * time.Millisecond)
 
+	// Check if the server failed to start
+	select {
+	case err := <-s.serverErr:
+		s.running = false
+		return err
+	default:
+	}
+
 	return nil
 }
 
@@ -269,7 +529,7 @@ func (s *serverInstance) Stop(ctx context.Context) error {
 	}
 
 	logger.Info("Gracefully shutting down server '%s'...", s.cfg.Name)
-	err := s.httpServer.Shutdown(ctx)
+	err := s.gracefulServer.shutdown(ctx)
 	if err == nil {
 		s.running = false
 	}
@@ -278,5 +538,35 @@ func (s *serverInstance) Stop(ctx context.Context) error {
 
 // Addr returns the network address the server is listening on.
 func (s *serverInstance) Addr() string {
-	return s.httpServer.Addr
+	return s.gracefulServer.server.Addr
+}
+
+// Name returns the server instance name.
+func (s *serverInstance) Name() string {
+	return s.cfg.Name
+}
+
+// HealthCheckHandler returns a handler that responds to health checks.
+func (s *serverInstance) HealthCheckHandler() http.HandlerFunc {
+	return s.gracefulServer.healthCheckHandler()
+}
+
+// ReadinessHandler returns a handler for readiness checks.
+func (s *serverInstance) ReadinessHandler() http.HandlerFunc {
+	return s.gracefulServer.readinessHandler()
+}
+
+// InFlightRequests returns the current number of in-flight requests.
+func (s *serverInstance) InFlightRequests() int64 {
+	return s.gracefulServer.inFlightRequestsCount()
+}
+
+// IsShuttingDown returns true if the server is shutting down.
+func (s *serverInstance) IsShuttingDown() bool {
+	return s.gracefulServer.isShutdown()
+}
+
+// Wait blocks until shutdown is complete.
+func (s *serverInstance) Wait() {
+	s.gracefulServer.wait()
 }
diff --git a/pkg/server/manager_test.go b/pkg/server/manager_test.go
index 1ff08f7..8ad123b 100644
--- a/pkg/server/manager_test.go
+++ b/pkg/server/manager_test.go
@@ -1,10 +1,12 @@
 package server
 
 import (
+	"context"
 	"fmt"
 	"io"
 	"net"
 	"net/http"
+	"sync"
 	"testing"
 	"time"
 
@@ -123,3 +125,204 @@ func TestManagerErrorCases(t *testing.T) {
 	_, err = sm.Add(config3)
 	require.Error(t, err, "should not be able to add a server with a nil handler")
 }
+
+func TestGracefulShutdown(t *testing.T) {
+	logger.Init(true)
+	sm := NewManager()
+
+	requestsHandled := 0
+	var requestsMu sync.Mutex
+
+	handler := http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		requestsMu.Lock()
+		requestsHandled++
+		requestsMu.Unlock()
+		time.Sleep(100 * time.Millisecond)
+		w.WriteHeader(http.StatusOK)
+	})
+
+	testPort := getFreePort(t)
+	instance, err := sm.Add(Config{
+		Name:         "TestServer",
+		Host:         "localhost",
+		Port:         testPort,
+		Handler:      handler,
+		DrainTimeout: 2 * time.Second,
+	})
+	require.NoError(t, err)
+
+	err = sm.StartAll()
+	require.NoError(t, err)
+
+	// Give server time to start
+	time.Sleep(100 * time.Millisecond)
+
+	// Send some concurrent requests
+	var wg sync.WaitGroup
+	for i := 0; i < 5; i++ {
+		wg.Add(1)
+		go func() {
+			defer wg.Done()
+			client := &http.Client{Timeout: 5 * time.Second}
+			url := fmt.Sprintf("http://localhost:%d", testPort)
+			resp, err := client.Get(url)
+			if err == nil {
+				resp.Body.Close()
+			}
+		}()
+	}
+
+	// Wait a bit for requests to start
+	time.Sleep(50 * time.Millisecond)
+
+	// Check in-flight requests
+	inFlight := instance.InFlightRequests()
+	assert.Greater(t, inFlight, int64(0), "Should have in-flight requests")
+
+	// Stop the server
+	err = sm.StopAll()
+	require.NoError(t, err)
+
+	// Wait for all requests to complete
+	wg.Wait()
+
+	// Verify all requests were handled
+	requestsMu.Lock()
+	handled := requestsHandled
+	requestsMu.Unlock()
+	assert.GreaterOrEqual(t, handled, 1, "At least some requests should have been handled")
+
+	// Verify no in-flight requests
+	assert.Equal(t, int64(0), instance.InFlightRequests(), "Should have no in-flight requests after shutdown")
+}
+
+func TestHealthAndReadinessEndpoints(t *testing.T) {
+	logger.Init(true)
+	sm := NewManager()
+
+	mux := http.NewServeMux()
+	testPort := getFreePort(t)
+
+	instance, err := sm.Add(Config{
+		Name:    "TestServer",
+		Host:    "localhost",
+		Port:    testPort,
+		Handler: mux,
+	})
+	require.NoError(t, err)
+
+	// Add health and readiness endpoints
+	mux.HandleFunc("/health", instance.HealthCheckHandler())
+	mux.HandleFunc("/ready", instance.ReadinessHandler())
+
+	err = sm.StartAll()
+	require.NoError(t, err)
+
+	time.Sleep(100 * time.Millisecond)
+
+	client := &http.Client{Timeout: 2 * time.Second}
+	baseURL := fmt.Sprintf("http://localhost:%d", testPort)
+
+	// Test health endpoint
+	resp, err := client.Get(baseURL + "/health")
+	require.NoError(t, err)
+	assert.Equal(t, http.StatusOK, resp.StatusCode)
+	body, _ := io.ReadAll(resp.Body)
+	resp.Body.Close()
+	assert.Contains(t, string(body), "healthy")
+
+	// Test readiness endpoint
+	resp, err = client.Get(baseURL + "/ready")
+	require.NoError(t, err)
+	assert.Equal(t, http.StatusOK, resp.StatusCode)
+	body, _ = io.ReadAll(resp.Body)
+	resp.Body.Close()
+	assert.Contains(t, string(body), "ready")
+	assert.Contains(t, string(body), "in_flight_requests")
+
+	// Stop the server
+	sm.StopAll()
+}
+
+func TestRequestRejectionDuringShutdown(t *testing.T) {
+	logger.Init(true)
+	sm := NewManager()
+
+	handler := http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		time.Sleep(50 * time.Millisecond)
+		w.WriteHeader(http.StatusOK)
+	})
+
+	testPort := getFreePort(t)
+	_, err := sm.Add(Config{
+		Name:         "TestServer",
+		Host:         "localhost",
+		Port:         testPort,
+		Handler:      handler,
+		DrainTimeout: 1 * time.Second,
+	})
+	require.NoError(t, err)
+
+	err = sm.StartAll()
+	require.NoError(t, err)
+
+	time.Sleep(100 * time.Millisecond)
+
+	// Start shutdown in background
+	go func() {
+		time.Sleep(50 * time.Millisecond)
+		sm.StopAll()
+	}()
+
+	// Give shutdown time to start
+	time.Sleep(100 * time.Millisecond)
+
+	// Try to make a request after shutdown started
+	client := &http.Client{Timeout: 2 * time.Second}
+	url := fmt.Sprintf("http://localhost:%d", testPort)
+	resp, err := client.Get(url)
+
+	// The request should either fail (connection refused) or get 503
+	if err == nil {
+		assert.Equal(t, http.StatusServiceUnavailable, resp.StatusCode, "Should get 503 during shutdown")
+		resp.Body.Close()
+	}
+}
+
+func TestShutdownCallbacks(t *testing.T) {
+	logger.Init(true)
+	sm := NewManager()
+
+	callbackExecuted := false
+	var callbackMu sync.Mutex
+
+	sm.RegisterShutdownCallback(func(ctx context.Context) error {
+		callbackMu.Lock()
+		callbackExecuted = true
+		callbackMu.Unlock()
+		return nil
+	})
+
+	testPort := getFreePort(t)
+	_, err := sm.Add(Config{
+		Name:    "TestServer",
+		Host:    "localhost",
+		Port:    testPort,
+		Handler: http.NewServeMux(),
+	})
+	require.NoError(t, err)
+
+	err = sm.StartAll()
+	require.NoError(t, err)
+
+	time.Sleep(100 * time.Millisecond)
+
+	err = sm.StopAll()
+	require.NoError(t, err)
+
+	callbackMu.Lock()
+	executed := callbackExecuted
+	callbackMu.Unlock()
+
+	assert.True(t, executed, "Shutdown callback should have been executed")
+}
diff --git a/pkg/server/shutdown.go b/pkg/server/shutdown.go
deleted file mode 100644
index 9960405..0000000
--- a/pkg/server/shutdown.go
+++ /dev/null
@@ -1,296 +0,0 @@
-package server
-
-import (
-	"context"
-	"fmt"
-	"net/http"
-	"os"
-	"os/signal"
-	"sync"
-	"sync/atomic"
-	"syscall"
-	"time"
-
-	"github.com/bitechdev/ResolveSpec/pkg/logger"
-)
-
-// GracefulServer wraps http.Server with graceful shutdown capabilities
-type GracefulServer struct {
-	server           *http.Server
-	shutdownTimeout  time.Duration
-	drainTimeout     time.Duration
-	inFlightRequests atomic.Int64
-	isShuttingDown   atomic.Bool
-	shutdownOnce     sync.Once
-	shutdownComplete chan struct{}
-}
-
-// Config holds configuration for the graceful server
-type Config struct {
-	// Addr is the server address (e.g., ":8080")
-	Addr string
-
-	// Handler is the HTTP handler
-	Handler http.Handler
-
-	// ShutdownTimeout is the maximum time to wait for graceful shutdown
-	// Default: 30 seconds
-	ShutdownTimeout time.Duration
-
-	// DrainTimeout is the time to wait for in-flight requests to complete
-	// before forcing shutdown. Default: 25 seconds
-	DrainTimeout time.Duration
-
-	// ReadTimeout is the maximum duration for reading the entire request
-	ReadTimeout time.Duration
-
-	// WriteTimeout is the maximum duration before timing out writes of the response
-	WriteTimeout time.Duration
-
-	// IdleTimeout is the maximum amount of time to wait for the next request
-	IdleTimeout time.Duration
-}
-
-// NewGracefulServer creates a new graceful server
-func NewGracefulServer(config Config) *GracefulServer {
-	if config.ShutdownTimeout == 0 {
-		config.ShutdownTimeout = 30 * time.Second
-	}
-	if config.DrainTimeout == 0 {
-		config.DrainTimeout = 25 * time.Second
-	}
-	if config.ReadTimeout == 0 {
-		config.ReadTimeout = 10 * time.Second
-	}
-	if config.WriteTimeout == 0 {
-		config.WriteTimeout = 10 * time.Second
-	}
-	if config.IdleTimeout == 0 {
-		config.IdleTimeout = 120 * time.Second
-	}
-
-	gs := &GracefulServer{
-		server: &http.Server{
-			Addr:         config.Addr,
-			Handler:      config.Handler,
-			ReadTimeout:  config.ReadTimeout,
-			WriteTimeout: config.WriteTimeout,
-			IdleTimeout:  config.IdleTimeout,
-		},
-		shutdownTimeout:  config.ShutdownTimeout,
-		drainTimeout:     config.DrainTimeout,
-		shutdownComplete: make(chan struct{}),
-	}
-
-	return gs
-}
-
-// TrackRequestsMiddleware tracks in-flight requests and blocks new requests during shutdown
-func (gs *GracefulServer) TrackRequestsMiddleware(next http.Handler) http.Handler {
-	return http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
-		// Check if shutting down
-		if gs.isShuttingDown.Load() {
-			http.Error(w, `{"error":"service_unavailable","message":"Server is shutting down"}`, http.StatusServiceUnavailable)
-			return
-		}
-
-		// Increment in-flight counter
-		gs.inFlightRequests.Add(1)
-		defer gs.inFlightRequests.Add(-1)
-
-		// Serve the request
-		next.ServeHTTP(w, r)
-	})
-}
-
-// ListenAndServe starts the server and handles graceful shutdown
-func (gs *GracefulServer) ListenAndServe() error {
-	// Wrap handler with request tracking
-	gs.server.Handler = gs.TrackRequestsMiddleware(gs.server.Handler)
-
-	// Start server in goroutine
-	serverErr := make(chan error, 1)
-	go func() {
-		logger.Info("Starting server on %s", gs.server.Addr)
-		if err := gs.server.ListenAndServe(); err != nil && err != http.ErrServerClosed {
-			serverErr <- err
-		}
-		close(serverErr)
-	}()
-
-	// Wait for interrupt signal
-	sigChan := make(chan os.Signal, 1)
-	signal.Notify(sigChan, os.Interrupt, syscall.SIGTERM, syscall.SIGINT)
-
-	select {
-	case err := <-serverErr:
-		return err
-	case sig := <-sigChan:
-		logger.Info("Received signal: %v, initiating graceful shutdown", sig)
-		return gs.Shutdown(context.Background())
-	}
-}
-
-// Shutdown performs graceful shutdown with request draining
-func (gs *GracefulServer) Shutdown(ctx context.Context) error {
-	var shutdownErr error
-
-	gs.shutdownOnce.Do(func() {
-		logger.Info("Starting graceful shutdown...")
-
-		// Mark as shutting down (new requests will be rejected)
-		gs.isShuttingDown.Store(true)
-
-		// Create context with timeout
-		shutdownCtx, cancel := context.WithTimeout(ctx, gs.shutdownTimeout)
-		defer cancel()
-
-		// Wait for in-flight requests to complete (with drain timeout)
-		drainCtx, drainCancel := context.WithTimeout(shutdownCtx, gs.drainTimeout)
-		defer drainCancel()
-
-		shutdownErr = gs.drainRequests(drainCtx)
-		if shutdownErr != nil {
-			logger.Error("Error draining requests: %v", shutdownErr)
-		}
-
-		// Shutdown the server
-		logger.Info("Shutting down HTTP server...")
-		if err := gs.server.Shutdown(shutdownCtx); err != nil {
-			logger.Error("Error shutting down server: %v", err)
-			if shutdownErr == nil {
-				shutdownErr = err
-			}
-		}
-
-		logger.Info("Graceful shutdown complete")
-		close(gs.shutdownComplete)
-	})
-
-	return shutdownErr
-}
-
-// drainRequests waits for in-flight requests to complete
-func (gs *GracefulServer) drainRequests(ctx context.Context) error {
-	ticker := time.NewTicker(100 * time.Millisecond)
-	defer ticker.Stop()
-
-	startTime := time.Now()
-
-	for {
-		inFlight := gs.inFlightRequests.Load()
-
-		if inFlight == 0 {
-			logger.Info("All requests drained in %v", time.Since(startTime))
-			return nil
-		}
-
-		select {
-		case <-ctx.Done():
-			logger.Warn("Drain timeout exceeded with %d requests still in flight", inFlight)
-			return fmt.Errorf("drain timeout exceeded: %d requests still in flight", inFlight)
-		case <-ticker.C:
-			logger.Debug("Waiting for %d in-flight requests to complete...", inFlight)
-		}
-	}
-}
-
-// InFlightRequests returns the current number of in-flight requests
-func (gs *GracefulServer) InFlightRequests() int64 {
-	return gs.inFlightRequests.Load()
-}
-
-// IsShuttingDown returns true if the server is shutting down
-func (gs *GracefulServer) IsShuttingDown() bool {
-	return gs.isShuttingDown.Load()
-}
-
-// Wait blocks until shutdown is complete
-func (gs *GracefulServer) Wait() {
-	<-gs.shutdownComplete
-}
-
-// HealthCheckHandler returns a handler that responds to health checks
-// Returns 200 OK when healthy, 503 Service Unavailable when shutting down
-func (gs *GracefulServer) HealthCheckHandler() http.HandlerFunc {
-	return func(w http.ResponseWriter, r *http.Request) {
-		if gs.IsShuttingDown() {
-			http.Error(w, `{"status":"shutting_down"}`, http.StatusServiceUnavailable)
-			return
-		}
-
-		w.Header().Set("Content-Type", "application/json")
-		w.WriteHeader(http.StatusOK)
-		_, err := w.Write([]byte(`{"status":"healthy"}`))
-		if err != nil {
-			logger.Warn("Failed to write. %v", err)
-		}
-	}
-}
-
-// ReadinessHandler returns a handler for readiness checks
-// Includes in-flight request count
-func (gs *GracefulServer) ReadinessHandler() http.HandlerFunc {
-	return func(w http.ResponseWriter, r *http.Request) {
-		if gs.IsShuttingDown() {
-			http.Error(w, `{"ready":false,"reason":"shutting_down"}`, http.StatusServiceUnavailable)
-			return
-		}
-
-		inFlight := gs.InFlightRequests()
-		w.Header().Set("Content-Type", "application/json")
-		w.WriteHeader(http.StatusOK)
-		fmt.Fprintf(w, `{"ready":true,"in_flight_requests":%d}`, inFlight)
-	}
-}
-
-// ShutdownCallback is a function called during shutdown
-type ShutdownCallback func(context.Context) error
-
-// shutdownCallbacks stores registered shutdown callbacks
-var (
-	shutdownCallbacks   []ShutdownCallback
-	shutdownCallbacksMu sync.Mutex
-)
-
-// RegisterShutdownCallback registers a callback to be called during shutdown
-// Useful for cleanup tasks like closing database connections, flushing metrics, etc.
-func RegisterShutdownCallback(cb ShutdownCallback) {
-	shutdownCallbacksMu.Lock()
-	defer shutdownCallbacksMu.Unlock()
-	shutdownCallbacks = append(shutdownCallbacks, cb)
-}
-
-// executeShutdownCallbacks runs all registered shutdown callbacks
-func executeShutdownCallbacks(ctx context.Context) error {
-	shutdownCallbacksMu.Lock()
-	callbacks := make([]ShutdownCallback, len(shutdownCallbacks))
-	copy(callbacks, shutdownCallbacks)
-	shutdownCallbacksMu.Unlock()
-
-	var errors []error
-	for i, cb := range callbacks {
-		logger.Debug("Executing shutdown callback %d/%d", i+1, len(callbacks))
-		if err := cb(ctx); err != nil {
-			logger.Error("Shutdown callback %d failed: %v", i+1, err)
-			errors = append(errors, err)
-		}
-	}
-
-	if len(errors) > 0 {
-		return fmt.Errorf("shutdown callbacks failed: %v", errors)
-	}
-
-	return nil
-}
-
-// ShutdownWithCallbacks performs shutdown and executes all registered callbacks
-func (gs *GracefulServer) ShutdownWithCallbacks(ctx context.Context) error {
-	// Execute callbacks first
-	if err := executeShutdownCallbacks(ctx); err != nil {
-		logger.Error("Error executing shutdown callbacks: %v", err)
-	}
-
-	// Then shutdown the server
-	return gs.Shutdown(ctx)
-}
diff --git a/pkg/server/shutdown_test.go b/pkg/server/shutdown_test.go
deleted file mode 100644
index 8eef439..0000000
--- a/pkg/server/shutdown_test.go
+++ /dev/null
@@ -1,231 +0,0 @@
-package server
-
-import (
-	"context"
-	"net/http"
-	"net/http/httptest"
-	"sync"
-	"testing"
-	"time"
-)
-
-func TestGracefulServerTrackRequests(t *testing.T) {
-	srv := NewGracefulServer(Config{
-		Addr: ":0",
-		Handler: http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
-			time.Sleep(100 * time.Millisecond)
-			w.WriteHeader(http.StatusOK)
-		}),
-	})
-
-	handler := srv.TrackRequestsMiddleware(srv.server.Handler)
-
-	// Start some requests
-	var wg sync.WaitGroup
-	for i := 0; i < 5; i++ {
-		wg.Add(1)
-		go func() {
-			defer wg.Done()
-			req := httptest.NewRequest("GET", "/test", nil)
-			w := httptest.NewRecorder()
-			handler.ServeHTTP(w, req)
-		}()
-	}
-
-	// Wait a bit for requests to start
-	time.Sleep(10 * time.Millisecond)
-
-	// Check in-flight count
-	inFlight := srv.InFlightRequests()
-	if inFlight == 0 {
-		t.Error("Should have in-flight requests")
-	}
-
-	// Wait for all requests to complete
-	wg.Wait()
-
-	// Check that counter is back to zero
-	inFlight = srv.InFlightRequests()
-	if inFlight != 0 {
-		t.Errorf("In-flight requests should be 0, got %d", inFlight)
-	}
-}
-
-func TestGracefulServerRejectsRequestsDuringShutdown(t *testing.T) {
-	srv := NewGracefulServer(Config{
-		Addr: ":0",
-		Handler: http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
-			w.WriteHeader(http.StatusOK)
-		}),
-	})
-
-	handler := srv.TrackRequestsMiddleware(srv.server.Handler)
-
-	// Mark as shutting down
-	srv.isShuttingDown.Store(true)
-
-	// Try to make a request
-	req := httptest.NewRequest("GET", "/test", nil)
-	w := httptest.NewRecorder()
-	handler.ServeHTTP(w, req)
-
-	// Should get 503
-	if w.Code != http.StatusServiceUnavailable {
-		t.Errorf("Expected 503, got %d", w.Code)
-	}
-}
-
-func TestHealthCheckHandler(t *testing.T) {
-	srv := NewGracefulServer(Config{
-		Addr:    ":0",
-		Handler: http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {}),
-	})
-
-	handler := srv.HealthCheckHandler()
-
-	// Healthy
-	t.Run("Healthy", func(t *testing.T) {
-		req := httptest.NewRequest("GET", "/health", nil)
-		w := httptest.NewRecorder()
-		handler.ServeHTTP(w, req)
-
-		if w.Code != http.StatusOK {
-			t.Errorf("Expected 200, got %d", w.Code)
-		}
-
-		if w.Body.String() != `{"status":"healthy"}` {
-			t.Errorf("Unexpected body: %s", w.Body.String())
-		}
-	})
-
-	// Shutting down
-	t.Run("ShuttingDown", func(t *testing.T) {
-		srv.isShuttingDown.Store(true)
-
-		req := httptest.NewRequest("GET", "/health", nil)
-		w := httptest.NewRecorder()
-		handler.ServeHTTP(w, req)
-
-		if w.Code != http.StatusServiceUnavailable {
-			t.Errorf("Expected 503, got %d", w.Code)
-		}
-	})
-}
-
-func TestReadinessHandler(t *testing.T) {
-	srv := NewGracefulServer(Config{
-		Addr:    ":0",
-		Handler: http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {}),
-	})
-
-	handler := srv.ReadinessHandler()
-
-	// Ready with no in-flight requests
-	t.Run("Ready", func(t *testing.T) {
-		req := httptest.NewRequest("GET", "/ready", nil)
-		w := httptest.NewRecorder()
-		handler.ServeHTTP(w, req)
-
-		if w.Code != http.StatusOK {
-			t.Errorf("Expected 200, got %d", w.Code)
-		}
-
-		body := w.Body.String()
-		if body != `{"ready":true,"in_flight_requests":0}` {
-			t.Errorf("Unexpected body: %s", body)
-		}
-	})
-
-	// Not ready during shutdown
-	t.Run("NotReady", func(t *testing.T) {
-		srv.isShuttingDown.Store(true)
-
-		req := httptest.NewRequest("GET", "/ready", nil)
-		w := httptest.NewRecorder()
-		handler.ServeHTTP(w, req)
-
-		if w.Code != http.StatusServiceUnavailable {
-			t.Errorf("Expected 503, got %d", w.Code)
-		}
-	})
-}
-
-func TestShutdownCallbacks(t *testing.T) {
-	callbackExecuted := false
-
-	RegisterShutdownCallback(func(ctx context.Context) error {
-		callbackExecuted = true
-		return nil
-	})
-
-	ctx := context.Background()
-	err := executeShutdownCallbacks(ctx)
-
-	if err != nil {
-		t.Errorf("executeShutdownCallbacks() error = %v", err)
-	}
-
-	if !callbackExecuted {
-		t.Error("Shutdown callback was not executed")
-	}
-
-	// Reset for other tests
-	shutdownCallbacks = nil
-}
-
-func TestDrainRequests(t *testing.T) {
-	srv := NewGracefulServer(Config{
-		Addr:         ":0",
-		Handler:      http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {}),
-		DrainTimeout: 1 * time.Second,
-	})
-
-	// Simulate in-flight requests
-	srv.inFlightRequests.Add(3)
-
-	// Start draining in background
-	go func() {
-		time.Sleep(100 * time.Millisecond)
-		// Simulate requests completing
-		srv.inFlightRequests.Add(-3)
-	}()
-
-	ctx, cancel := context.WithTimeout(context.Background(), 2*time.Second)
-	defer cancel()
-
-	err := srv.drainRequests(ctx)
-	if err != nil {
-		t.Errorf("drainRequests() error = %v", err)
-	}
-
-	if srv.InFlightRequests() != 0 {
-		t.Errorf("In-flight requests should be 0, got %d", srv.InFlightRequests())
-	}
-}
-
-func TestDrainRequestsTimeout(t *testing.T) {
-	srv := NewGracefulServer(Config{
-		Addr:         ":0",
-		Handler:      http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {}),
-		DrainTimeout: 100 * time.Millisecond,
-	})
-
-	// Simulate in-flight requests that don't complete
-	srv.inFlightRequests.Add(5)
-
-	ctx, cancel := context.WithTimeout(context.Background(), 200*time.Millisecond)
-	defer cancel()
-
-	err := srv.drainRequests(ctx)
-	if err == nil {
-		t.Error("drainRequests() should timeout with error")
-	}
-
-	// Cleanup
-	srv.inFlightRequests.Add(-5)
-}
-
-func TestGetClientIP(t *testing.T) {
-	// This test is in ratelimit_test.go since getClientIP is used by rate limiter
-	// Including here for completeness of server tests
-}
diff --git a/pkg/server/tls.go b/pkg/server/tls.go
new file mode 100644
index 0000000..5961291
--- /dev/null
+++ b/pkg/server/tls.go
@@ -0,0 +1,190 @@
+package server
+
+import (
+	"crypto/ecdsa"
+	"crypto/elliptic"
+	"crypto/rand"
+	"crypto/tls"
+	"crypto/x509"
+	"crypto/x509/pkix"
+	"encoding/pem"
+	"fmt"
+	"math/big"
+	"net"
+	"os"
+	"path/filepath"
+	"time"
+
+	"golang.org/x/crypto/acme/autocert"
+)
+
+// generateSelfSignedCert generates a self-signed certificate for the given host.
+// Returns the certificate and private key in PEM format.
+func generateSelfSignedCert(host string) (certPEM, keyPEM []byte, err error) {
+	// Generate private key
+	priv, err := ecdsa.GenerateKey(elliptic.P256(), rand.Reader)
+	if err != nil {
+		return nil, nil, fmt.Errorf("failed to generate private key: %w", err)
+	}
+
+	// Create certificate template
+	notBefore := time.Now()
+	notAfter := notBefore.Add(365 * 24 * time.Hour) // Valid for 1 year
+
+	serialNumber, err := rand.Int(rand.Reader, new(big.Int).Lsh(big.NewInt(1), 128))
+	if err != nil {
+		return nil, nil, fmt.Errorf("failed to generate serial number: %w", err)
+	}
+
+	template := x509.Certificate{
+		SerialNumber: serialNumber,
+		Subject: pkix.Name{
+			Organization: []string{"ResolveSpec Self-Signed"},
+			CommonName:   host,
+		},
+		NotBefore:             notBefore,
+		NotAfter:              notAfter,
+		KeyUsage:              x509.KeyUsageKeyEncipherment | x509.KeyUsageDigitalSignature,
+		ExtKeyUsage:           []x509.ExtKeyUsage{x509.ExtKeyUsageServerAuth},
+		BasicConstraintsValid: true,
+	}
+
+	// Add host as DNS name or IP address
+	if ip := net.ParseIP(host); ip != nil {
+		template.IPAddresses = []net.IP{ip}
+	} else {
+		template.DNSNames = []string{host}
+	}
+
+	// Create certificate
+	derBytes, err := x509.CreateCertificate(rand.Reader, &template, &template, &priv.PublicKey, priv)
+	if err != nil {
+		return nil, nil, fmt.Errorf("failed to create certificate: %w", err)
+	}
+
+	// Encode certificate to PEM
+	certPEM = pem.EncodeToMemory(&pem.Block{Type: "CERTIFICATE", Bytes: derBytes})
+
+	// Encode private key to PEM
+	privBytes, err := x509.MarshalECPrivateKey(priv)
+	if err != nil {
+		return nil, nil, fmt.Errorf("failed to marshal private key: %w", err)
+	}
+	keyPEM = pem.EncodeToMemory(&pem.Block{Type: "EC PRIVATE KEY", Bytes: privBytes})
+
+	return certPEM, keyPEM, nil
+}
+
+// saveCertToTempFiles saves certificate and key PEM data to temporary files.
+// Returns the file paths for the certificate and key.
+func saveCertToTempFiles(certPEM, keyPEM []byte) (certFile, keyFile string, err error) {
+	// Create temporary directory
+	tmpDir, err := os.MkdirTemp("", "resolvespec-certs-*")
+	if err != nil {
+		return "", "", fmt.Errorf("failed to create temp directory: %w", err)
+	}
+
+	certFile = filepath.Join(tmpDir, "cert.pem")
+	keyFile = filepath.Join(tmpDir, "key.pem")
+
+	// Write certificate
+	if err := os.WriteFile(certFile, certPEM, 0600); err != nil {
+		os.RemoveAll(tmpDir)
+		return "", "", fmt.Errorf("failed to write certificate: %w", err)
+	}
+
+	// Write key
+	if err := os.WriteFile(keyFile, keyPEM, 0600); err != nil {
+		os.RemoveAll(tmpDir)
+		return "", "", fmt.Errorf("failed to write private key: %w", err)
+	}
+
+	return certFile, keyFile, nil
+}
+
+// setupAutoTLS configures automatic TLS certificate management using Let's Encrypt.
+// Returns a TLS config that can be used with http.Server.
+func setupAutoTLS(domains []string, email, cacheDir string) (*tls.Config, error) {
+	if len(domains) == 0 {
+		return nil, fmt.Errorf("at least one domain must be specified for AutoTLS")
+	}
+
+	// Set default cache directory
+	if cacheDir == "" {
+		cacheDir = "./certs-cache"
+	}
+
+	// Create cache directory if it doesn't exist
+	if err := os.MkdirAll(cacheDir, 0700); err != nil {
+		return nil, fmt.Errorf("failed to create certificate cache directory: %w", err)
+	}
+
+	// Create autocert manager
+	m := &autocert.Manager{
+		Prompt:      autocert.AcceptTOS,
+		Cache:       autocert.DirCache(cacheDir),
+		HostPolicy:  autocert.HostWhitelist(domains...),
+		Email:       email,
+	}
+
+	// Create TLS config
+	tlsConfig := m.TLSConfig()
+	tlsConfig.MinVersion = tls.VersionTLS12
+
+	return tlsConfig, nil
+}
+
+// configureTLS configures TLS for the server based on the provided configuration.
+// Returns the TLS config and certificate/key file paths (if applicable).
+func configureTLS(cfg Config) (*tls.Config, string, string, error) {
+	// Option 1: Certificate files provided
+	if cfg.SSLCert != "" && cfg.SSLKey != "" {
+		// Validate that files exist
+		if _, err := os.Stat(cfg.SSLCert); os.IsNotExist(err) {
+			return nil, "", "", fmt.Errorf("SSL certificate file not found: %s", cfg.SSLCert)
+		}
+		if _, err := os.Stat(cfg.SSLKey); os.IsNotExist(err) {
+			return nil, "", "", fmt.Errorf("SSL key file not found: %s", cfg.SSLKey)
+		}
+
+		// Return basic TLS config - cert/key will be loaded by ListenAndServeTLS
+		tlsConfig := &tls.Config{
+			MinVersion: tls.VersionTLS12,
+		}
+		return tlsConfig, cfg.SSLCert, cfg.SSLKey, nil
+	}
+
+	// Option 2: Auto TLS (Let's Encrypt)
+	if cfg.AutoTLS {
+		tlsConfig, err := setupAutoTLS(cfg.AutoTLSDomains, cfg.AutoTLSEmail, cfg.AutoTLSCacheDir)
+		if err != nil {
+			return nil, "", "", fmt.Errorf("failed to setup AutoTLS: %w", err)
+		}
+		return tlsConfig, "", "", nil
+	}
+
+	// Option 3: Self-signed certificate
+	if cfg.SelfSignedSSL {
+		host := cfg.Host
+		if host == "" || host == "0.0.0.0" {
+			host = "localhost"
+		}
+
+		certPEM, keyPEM, err := generateSelfSignedCert(host)
+		if err != nil {
+			return nil, "", "", fmt.Errorf("failed to generate self-signed certificate: %w", err)
+		}
+
+		certFile, keyFile, err := saveCertToTempFiles(certPEM, keyPEM)
+		if err != nil {
+			return nil, "", "", fmt.Errorf("failed to save self-signed certificate: %w", err)
+		}
+
+		tlsConfig := &tls.Config{
+			MinVersion: tls.VersionTLS12,
+		}
+		return tlsConfig, certFile, keyFile, nil
+	}
+
+	return nil, "", "", nil
+}