diff --git a/cmd/server/main.go b/cmd/server/main.go
index dee87ae..ca674b8 100644
--- a/cmd/server/main.go
+++ b/cmd/server/main.go
@@ -38,7 +38,7 @@ func main() {
 	configPath := os.Getenv("LLAMACTL_CONFIG_PATH")
 	cfg, err := config.LoadConfig(configPath)
 	if err != nil {
-		fmt.Printf("Error loading config: %v\n", err)
+		fmt.Printf("Error loading config: %w\n", err)
 		fmt.Println("Using default configuration.")
 	}
 
@@ -50,12 +50,12 @@ func main() {
 	// Create the data directory if it doesn't exist
 	if cfg.Instances.AutoCreateDirs {
 		if err := os.MkdirAll(cfg.Instances.InstancesDir, 0755); err != nil {
-			fmt.Printf("Error creating config directory %s: %v\n", cfg.Instances.InstancesDir, err)
+			fmt.Printf("Error creating config directory %s: %w\n", cfg.Instances.InstancesDir, err)
 			fmt.Println("Persistence will not be available.")
 		}
 
 		if err := os.MkdirAll(cfg.Instances.LogsDir, 0755); err != nil {
-			fmt.Printf("Error creating log directory %s: %v\n", cfg.Instances.LogsDir, err)
+			fmt.Printf("Error creating log directory %s: %w\n", cfg.Instances.LogsDir, err)
 			fmt.Println("Instance logs will not be available.")
 		}
 	}
@@ -81,7 +81,7 @@ func main() {
 	go func() {
 		fmt.Printf("Llamactl server listening on %s:%d\n", cfg.Server.Host, cfg.Server.Port)
 		if err := server.ListenAndServe(); err != nil && err != http.ErrServerClosed {
-			fmt.Printf("Error starting server: %v\n", err)
+			fmt.Printf("Error starting server: %w\n", err)
 		}
 	}()
 
@@ -90,7 +90,7 @@ func main() {
 	fmt.Println("Shutting down server...")
 
 	if err := server.Close(); err != nil {
-		fmt.Printf("Error shutting down server: %v\n", err)
+		fmt.Printf("Error shutting down server: %w\n", err)
 	} else {
 		fmt.Println("Server shut down gracefully.")
 	}
diff --git a/pkg/instance/process.go b/pkg/instance/process.go
index 94e057f..89db565 100644
--- a/pkg/instance/process.go
+++ b/pkg/instance/process.go
@@ -143,7 +143,7 @@ func (p *process) stop() error {
 	// Stop the process with SIGINT if cmd exists
 	if p.cmd != nil && p.cmd.Process != nil {
 		if err := p.cmd.Process.Signal(syscall.SIGINT); err != nil {
-			log.Printf("Failed to send SIGINT to instance %s: %v", p.instance.Name, err)
+			log.Printf("Failed to send SIGINT to instance %s: %w", p.instance.Name, err)
 		}
 	}
 
@@ -161,7 +161,7 @@ func (p *process) stop() error {
 		if p.cmd != nil && p.cmd.Process != nil {
 			killErr := p.cmd.Process.Kill()
 			if killErr != nil {
-				log.Printf("Failed to force kill instance %s: %v", p.instance.Name, killErr)
+				log.Printf("Failed to force kill instance %s: %w", p.instance.Name, killErr)
 			}
 			log.Printf("Instance %s did not stop in time, force killed", p.instance.Name)
 
@@ -292,7 +292,7 @@ func (p *process) monitorProcess() {
 
 	// Log the exit
 	if err != nil {
-		log.Printf("Instance %s crashed with error: %v", p.instance.Name, err)
+		log.Printf("Instance %s crashed with error: %w", p.instance.Name, err)
 		// Handle auto-restart logic
 		p.handleAutoRestart(err)
 	} else {
@@ -376,7 +376,7 @@ func (p *process) handleAutoRestart(err error) {
 
 	// Restart the instance
 	if err := p.start(); err != nil {
-		log.Printf("Failed to restart instance %s: %v", p.instance.Name, err)
+		log.Printf("Failed to restart instance %s: %w", p.instance.Name, err)
 	} else {
 		log.Printf("Successfully restarted instance %s", p.instance.Name)
 		// Clear the cancel function
diff --git a/pkg/manager/lifecycle.go b/pkg/manager/lifecycle.go
index cc147df..7d052f1 100644
--- a/pkg/manager/lifecycle.go
+++ b/pkg/manager/lifecycle.go
@@ -102,7 +102,7 @@ func (l *lifecycleManager) checkTimeouts() {
 	for _, name := range timeoutInstances {
 		log.Printf("Instance %s has timed out, stopping it", name)
 		if _, err := l.manager.StopInstance(name); err != nil {
-			log.Printf("Error stopping instance %s: %v", name, err)
+			log.Printf("Error stopping instance %s: %w", name, err)
 		} else {
 			log.Printf("Instance %s stopped successfully", name)
 		}
diff --git a/pkg/manager/manager.go b/pkg/manager/manager.go
index 3f3733a..2ed3a2a 100644
--- a/pkg/manager/manager.go
+++ b/pkg/manager/manager.go
@@ -56,13 +56,13 @@ func New(globalConfig *config.AppConfig) InstanceManager {
 	portRange := globalConfig.Instances.PortRange
 	ports, err := newPortAllocator(portRange[0], portRange[1])
 	if err != nil {
-		log.Fatalf("Failed to create port allocator: %v", err)
+		log.Fatalf("Failed to create port allocator: %w", err)
 	}
 
 	// Initialize persistence
 	persistence, err := newInstancePersister(globalConfig.Instances.InstancesDir)
 	if err != nil {
-		log.Fatalf("Failed to create instance persister: %v", err)
+		log.Fatalf("Failed to create instance persister: %w", err)
 	}
 
 	// Initialize remote manager
@@ -83,7 +83,7 @@ func New(globalConfig *config.AppConfig) InstanceManager {
 
 	// Load existing instances from disk
 	if err := im.loadInstances(); err != nil {
-		log.Printf("Error loading instances: %v", err)
+		log.Printf("Error loading instances: %w", err)
 	}
 
 	// Start the lifecycle manager
@@ -116,7 +116,7 @@ func (im *instanceManager) Shutdown() {
 				defer wg.Done()
 				fmt.Printf("Stopping instance %s...\n", inst.Name)
 				if err := inst.Stop(); err != nil {
-					fmt.Printf("Error stopping instance %s: %v\n", inst.Name, err)
+					fmt.Printf("Error stopping instance %s: %w\n", inst.Name, err)
 				}
 			}(inst)
 		}
@@ -140,7 +140,7 @@ func (im *instanceManager) loadInstances() error {
 	// Process each loaded instance
 	for _, persistedInst := range instances {
 		if err := im.loadInstance(persistedInst); err != nil {
-			log.Printf("Failed to load instance %s: %v", persistedInst.Name, err)
+			log.Printf("Failed to load instance %s: %w", persistedInst.Name, err)
 			continue
 		}
 	}
@@ -251,12 +251,12 @@ func (im *instanceManager) autoStartInstances() {
 			// Remote instance - use remote manager with context
 			ctx := context.Background()
 			if _, err := im.remote.startInstance(ctx, node, inst.Name); err != nil {
-				log.Printf("Failed to auto-start remote instance %s: %v", inst.Name, err)
+				log.Printf("Failed to auto-start remote instance %s: %w", inst.Name, err)
 			}
 		} else {
 			// Local instance - call Start() directly
 			if err := inst.Start(); err != nil {
-				log.Printf("Failed to auto-start instance %s: %v", inst.Name, err)
+				log.Printf("Failed to auto-start instance %s: %w", inst.Name, err)
 			}
 		}
 	}
diff --git a/pkg/manager/operations.go b/pkg/manager/operations.go
index 14b86a7..a94e2e5 100644
--- a/pkg/manager/operations.go
+++ b/pkg/manager/operations.go
@@ -166,7 +166,7 @@ func (im *instanceManager) CreateInstance(name string, options *instance.Options
 
 	// Persist instance (best-effort, don't fail if persistence fails)
 	if err := im.persistInstance(inst); err != nil {
-		log.Printf("Warning: failed to persist instance %s: %v", name, err)
+		log.Printf("Warning: failed to persist instance %s: %w", name, err)
 	}
 
 	return inst, nil
@@ -394,7 +394,7 @@ func (im *instanceManager) StartInstance(name string) (*instance.Instance, error
 
 	// Persist instance (best-effort, don't fail if persistence fails)
 	if err := im.persistInstance(inst); err != nil {
-		log.Printf("Warning: failed to persist instance %s: %v", name, err)
+		log.Printf("Warning: failed to persist instance %s: %w", name, err)
 	}
 
 	return inst, nil
@@ -453,7 +453,7 @@ func (im *instanceManager) StopInstance(name string) (*instance.Instance, error)
 
 	// Persist instance (best-effort, don't fail if persistence fails)
 	if err := im.persistInstance(inst); err != nil {
-		log.Printf("Warning: failed to persist instance %s: %v", name, err)
+		log.Printf("Warning: failed to persist instance %s: %w", name, err)
 	}
 
 	return inst, nil
@@ -499,7 +499,7 @@ func (im *instanceManager) RestartInstance(name string) (*instance.Instance, err
 
 	// Persist the restarted instance
 	if err := im.persistInstance(inst); err != nil {
-		log.Printf("Warning: failed to persist instance %s: %v", name, err)
+		log.Printf("Warning: failed to persist instance %s: %w", name, err)
 	}
 
 	return inst, nil
diff --git a/pkg/manager/persistence.go b/pkg/manager/persistence.go
index 01fe11f..8bad44f 100644
--- a/pkg/manager/persistence.go
+++ b/pkg/manager/persistence.go
@@ -162,8 +162,8 @@ func (p *instancePersister) loadAll() ([]*instance.Instance, error) {
 
 		inst, err := p.loadInstanceFile(instanceName, instancePath)
 		if err != nil {
-			log.Printf("Failed to load instance %s: %v", instanceName, err)
-			loadErrors = append(loadErrors, fmt.Sprintf("%s: %v", instanceName, err))
+			log.Printf("Failed to load instance %s: %w", instanceName, err)
+			loadErrors = append(loadErrors, fmt.Sprintf("%s: %w", instanceName, err))
 			continue
 		}
 
diff --git a/pkg/server/handlers.go b/pkg/server/handlers.go
index 78b83c5..390c130 100644
--- a/pkg/server/handlers.go
+++ b/pkg/server/handlers.go
@@ -25,7 +25,7 @@ func writeError(w http.ResponseWriter, status int, code, details string) {
 	w.Header().Set("Content-Type", "application/json")
 	w.WriteHeader(status)
 	if err := json.NewEncoder(w).Encode(errorResponse{Error: code, Details: details}); err != nil {
-		log.Printf("Failed to encode error response: %v", err)
+		log.Printf("Failed to encode error response: %w", err)
 	}
 }
 
@@ -34,7 +34,7 @@ func writeJSON(w http.ResponseWriter, status int, data any) {
 	w.Header().Set("Content-Type", "application/json")
 	w.WriteHeader(status)
 	if err := json.NewEncoder(w).Encode(data); err != nil {
-		log.Printf("Failed to encode JSON response: %v", err)
+		log.Printf("Failed to encode JSON response: %w", err)
 	}
 }
 
@@ -43,7 +43,7 @@ func writeText(w http.ResponseWriter, status int, data string) {
 	w.Header().Set("Content-Type", "text/plain")
 	w.WriteHeader(status)
 	if _, err := w.Write([]byte(data)); err != nil {
-		log.Printf("Failed to write text response: %v", err)
+		log.Printf("Failed to write text response: %w", err)
 	}
 }
 
diff --git a/pkg/server/routes.go b/pkg/server/routes.go
index 6587601..87c9148 100644
--- a/pkg/server/routes.go
+++ b/pkg/server/routes.go
@@ -159,7 +159,7 @@ func SetupRouter(handler *Handler) *chi.Mux {
 
 	// Serve WebUI files
 	if err := webui.SetupWebUI(r); err != nil {
-		fmt.Printf("Failed to set up WebUI: %v\n", err)
+		fmt.Printf("Failed to set up WebUI: %w\n", err)
 	}
 
 	return r