diff --git a/cmd/picoclaw/main_test.go b/cmd/picoclaw/main_test.go
index cb221dece..f18013371 100644
--- a/cmd/picoclaw/main_test.go
+++ b/cmd/picoclaw/main_test.go
@@ -9,7 +9,9 @@ import (
 	"github.com/stretchr/testify/require"
 
 	"github.com/sipeed/picoclaw/cmd/picoclaw/internal"
+	"github.com/sipeed/picoclaw/pkg/agent"
 	"github.com/sipeed/picoclaw/pkg/config"
+	"github.com/sipeed/picoclaw/pkg/security"
 )
 
 func TestNewPicoclawCommand(t *testing.T) {
@@ -57,3 +59,24 @@ func TestNewPicoclawCommand(t *testing.T) {
 		assert.False(t, subcmd.Hidden)
 	}
 }
+
+func TestSecurityShieldRegistration_Regression(t *testing.T) {
+	// Initialize security hooks (registers them in pkg/agent)
+	security.Init()
+
+	expectedHooks := []string{
+		"security_policy",
+		"security_canary",
+		"security_behavior",
+		"security_pii",
+		"security_ipia",
+	}
+
+	for _, name := range expectedHooks {
+		t.Run(name, func(t *testing.T) {
+			assert.True(t, agent.IsBuiltinHookRegistered(name),
+				"Builtin hook %q is not registered. This usually means pkg/security was deleted "+
+					"or security.Init() is no longer called in main().", name)
+		})
+	}
+}
diff --git a/pkg/agent/hook_mount.go b/pkg/agent/hook_mount.go
index c92145f1f..aa2e38d60 100644
--- a/pkg/agent/hook_mount.go
+++ b/pkg/agent/hook_mount.go
@@ -8,8 +8,17 @@ import (
 	"time"
 
 	"github.com/sipeed/picoclaw/pkg/config"
+	"github.com/sipeed/picoclaw/pkg/logger"
 )
 
+// IsBuiltinHookRegistered returns true if a builtin hook factory is registered with the given name.
+func IsBuiltinHookRegistered(name string) bool {
+	builtinHookRegistryMu.RLock()
+	defer builtinHookRegistryMu.RUnlock()
+	_, exists := builtinHookRegistry[name]
+	return exists
+}
+
 type hookRuntime struct {
 	initOnce sync.Once
 	mu       sync.Mutex
@@ -143,19 +152,25 @@ func (al *AgentLoop) loadConfiguredHooks(ctx context.Context) (err error) {
 		spec := al.cfg.Hooks.Builtins[name]
 		factory, ok := lookupBuiltinHook(name)
 		if !ok {
+			logger.WarnCF("agent", "Builtin hook not registered", map[string]any{"hook": name})
 			return fmt.Errorf("builtin hook %q is not registered", name)
 		}
 
+		logger.DebugCF("agent", "Executing builtin hook factory", map[string]any{"hook": name})
 		hook, factoryErr := factory(ctx, spec)
 		if factoryErr != nil {
+			logger.ErrorCF("agent", "Builtin hook factory failed", map[string]any{"hook": name, "error": factoryErr.Error()})
 			return fmt.Errorf("build builtin hook %q: %w", name, factoryErr)
 		}
+		logger.DebugCF("agent", "Builtin hook factory finished", map[string]any{"hook": name})
+
 		if err := al.MountHook(HookRegistration{
 			Name:     name,
 			Priority: spec.Priority,
 			Source:   HookSourceInProcess,
 			Hook:     hook,
 		}); err != nil {
+			logger.ErrorCF("agent", "Failed to mount builtin hook", map[string]any{"hook": name, "error": err.Error()})
 			return fmt.Errorf("mount builtin hook %q: %w", name, err)
 		}
 		mounted = append(mounted, name)
diff --git a/pkg/security/policy/checker.go b/pkg/security/policy/checker.go
index f4b5e13b7..eb51ea467 100644
--- a/pkg/security/policy/checker.go
+++ b/pkg/security/policy/checker.go
@@ -55,7 +55,7 @@ func (c *Checker) ApproveTool(ctx context.Context, req *agent.ToolApprovalReques
 		if c.Config.AllowedTools[req.Tool] {
 			allowed = true
 		} else {
-			// Check for prefix matches (e.g. "monday" matches "mcp_monday_...")
+			// Check for prefix matches (e.g. "github" matches "mcp_github_...")
 			// Match logic consistent with ToolRegistry.Filter
 			for w, ok := range c.Config.AllowedTools {
 				if !ok {