Add opt-in PII redaction with typed tokens

cmd/entire/cli/checkpoint/temporary.go

@@ -922,6 +922,8 @@ func addDirectoryToEntriesWithAbsPath(repo *git.Repository, dirPathAbs, dirPathR
 
 		treePath := filepath.ToSlash(filepath.Join(dirPathRel, relWithinDir))
 
+		// Use redacted blob creation for metadata files (transcripts, prompts, etc.)
+		// to ensure PII and secrets are redacted before writing to git.
 		blobHash, mode, err := createRedactedBlobFromFile(repo, path, treePath)
 		if err != nil {
 			return fmt.Errorf("failed to create blob for %s: %w", path, err)

cmd/entire/cli/settings/settings.go

@@ -49,6 +49,24 @@ type EntireSettings struct {
 	// Telemetry controls anonymous usage analytics.
 	// nil = not asked yet (show prompt), true = opted in, false = opted out
 	Telemetry *bool `json:"telemetry,omitempty"`
+
+	// Redaction configures PII redaction behavior for transcripts and metadata.
+	Redaction *RedactionSettings `json:"redaction,omitempty"`
+}
+
+// RedactionSettings configures redaction behavior beyond the default secret detection.
+type RedactionSettings struct {
+	PII *PIISettings `json:"pii,omitempty"`
+}
+
+// PIISettings configures PII detection categories.
+// When Enabled is true, email and phone default to true; address defaults to false.
+type PIISettings struct {
+	Enabled        bool              `json:"enabled"`
+	Email          *bool             `json:"email,omitempty"`
+	Phone          *bool             `json:"phone,omitempty"`
+	Address        *bool             `json:"address,omitempty"`
+	CustomPatterns map[string]string `json:"custom_patterns,omitempty"`
 }
 
 // Load loads the Entire settings from .entire/settings.json,
@@ -204,6 +222,15 @@ func mergeJSON(settings *EntireSettings, data []byte) error {
 		settings.Telemetry = &t
 	}
 
+	// Override redaction if present
+	if redactionRaw, ok := raw["redaction"]; ok {
+		var r RedactionSettings
+		if err := json.Unmarshal(redactionRaw, &r); err != nil {
+			return fmt.Errorf("parsing redaction field: %w", err)
+		}
+		settings.Redaction = &r
+	}
+
 	return nil
 }
 

cmd/entire/cli/settings/settings_test.go

@@ -59,7 +59,8 @@ func TestLoad_AcceptsValidKeys(t *testing.T) {
 		"local_dev": false,
 		"log_level": "debug",
 		"strategy_options": {"key": "value"},
-		"telemetry": true
+		"telemetry": true,
+		"redaction": {"pii": {"enabled": true, "email": true, "phone": false}}
 	}`
 	if err := os.WriteFile(settingsFile, []byte(settingsContent), 0644); err != nil {
 		t.Fatalf("failed to write settings file: %v", err)
@@ -92,6 +93,21 @@ func TestLoad_AcceptsValidKeys(t *testing.T) {
 	if settings.Telemetry == nil || !*settings.Telemetry {
 		t.Error("expected telemetry to be true")
 	}
+	if settings.Redaction == nil {
+		t.Fatal("expected redaction to be non-nil")
+	}
+	if settings.Redaction.PII == nil {
+		t.Fatal("expected redaction.pii to be non-nil")
+	}
+	if !settings.Redaction.PII.Enabled {
+		t.Error("expected redaction.pii.enabled to be true")
+	}
+	if settings.Redaction.PII.Email == nil || !*settings.Redaction.PII.Email {
+		t.Error("expected redaction.pii.email to be true")
+	}
+	if settings.Redaction.PII.Phone == nil || *settings.Redaction.PII.Phone {
+		t.Error("expected redaction.pii.phone to be false")
+	}
 }
 
 func TestLoad_LocalSettingsRejectsUnknownKeys(t *testing.T) {
@@ -135,6 +151,74 @@ func TestLoad_LocalSettingsRejectsUnknownKeys(t *testing.T) {
 	}
 }
 
+func TestLoad_MissingRedactionIsNil(t *testing.T) {
+	tmpDir := t.TempDir()
+	entireDir := filepath.Join(tmpDir, ".entire")
+	if err := os.MkdirAll(entireDir, 0755); err != nil {
+		t.Fatalf("failed to create .entire directory: %v", err)
+	}
+
+	settingsFile := filepath.Join(entireDir, "settings.json")
+	if err := os.WriteFile(settingsFile, []byte(`{"strategy": "manual-commit"}`), 0644); err != nil {
+		t.Fatalf("failed to write settings file: %v", err)
+	}
+	if err := os.MkdirAll(filepath.Join(tmpDir, ".git"), 0755); err != nil {
+		t.Fatalf("failed to create .git directory: %v", err)
+	}
+	t.Chdir(tmpDir)
+
+	settings, err := Load()
+	if err != nil {
+		t.Fatalf("unexpected error: %v", err)
+	}
+	if settings.Redaction != nil {
+		t.Error("expected redaction to be nil when not in settings")
+	}
+}
+
+func TestLoad_LocalOverridesRedaction(t *testing.T) {
+	tmpDir := t.TempDir()
+	entireDir := filepath.Join(tmpDir, ".entire")
+	if err := os.MkdirAll(entireDir, 0755); err != nil {
+		t.Fatalf("failed to create .entire directory: %v", err)
+	}
+
+	// Base settings: PII disabled
+	settingsFile := filepath.Join(entireDir, "settings.json")
+	if err := os.WriteFile(settingsFile, []byte(`{"strategy": "manual-commit", "redaction": {"pii": {"enabled": false}}}`), 0644); err != nil {
+		t.Fatalf("failed to write settings file: %v", err)
+	}
+
+	// Local override: PII enabled with custom patterns
+	localFile := filepath.Join(entireDir, "settings.local.json")
+	localContent := `{"redaction": {"pii": {"enabled": true, "custom_patterns": {"employee_id": "EMP-\\d{6}"}}}}`
+	if err := os.WriteFile(localFile, []byte(localContent), 0644); err != nil {
+		t.Fatalf("failed to write local settings file: %v", err)
+	}
+
+	if err := os.MkdirAll(filepath.Join(tmpDir, ".git"), 0755); err != nil {
+		t.Fatalf("failed to create .git directory: %v", err)
+	}
+	t.Chdir(tmpDir)
+
+	settings, err := Load()
+	if err != nil {
+		t.Fatalf("unexpected error: %v", err)
+	}
+	if settings.Redaction == nil || settings.Redaction.PII == nil {
+		t.Fatal("expected redaction.pii to be non-nil after local override")
+	}
+	if !settings.Redaction.PII.Enabled {
+		t.Error("expected local override to enable PII")
+	}
+	if settings.Redaction.PII.CustomPatterns == nil {
+		t.Fatal("expected custom_patterns to be non-nil")
+	}
+	if settings.Redaction.PII.CustomPatterns["employee_id"] != `EMP-\d{6}` {
+		t.Errorf("expected employee_id pattern, got %v", settings.Redaction.PII.CustomPatterns)
+	}
+}
+
 // containsUnknownField checks if the error message indicates an unknown field
 func containsUnknownField(msg string) bool {
 	// Go's json package reports unknown fields with this message format

cmd/entire/cli/strategy/auto_commit.go

@@ -121,6 +121,8 @@ func (s *AutoCommitStrategy) PrePush(remote string) error {
 }
 
 func (s *AutoCommitStrategy) SaveStep(ctx StepContext) error {
+	EnsureRedactionConfigured()
+
 	repo, err := OpenRepository()
 	if err != nil {
 		return fmt.Errorf("failed to open git repository: %w", err)
@@ -501,6 +503,7 @@ func (s *AutoCommitStrategy) GetSessionInfo() (*SessionInfo, error) {
 // 1. Commit code changes to active branch (no trailers - clean history)
 // 2. Commit task metadata to entire/checkpoints/v1 branch with checkpoint format
 func (s *AutoCommitStrategy) SaveTaskStep(ctx TaskStepContext) error {
+	EnsureRedactionConfigured()
 	repo, err := OpenRepository()
 	if err != nil {
 		return fmt.Errorf("failed to open git repository: %w", err)

cmd/entire/cli/strategy/common.go

@@ -17,7 +17,9 @@ import (
 	"github.com/entireio/cli/cmd/entire/cli/checkpoint"
 	"github.com/entireio/cli/cmd/entire/cli/checkpoint/id"
 	"github.com/entireio/cli/cmd/entire/cli/paths"
+	"github.com/entireio/cli/cmd/entire/cli/settings"
 	"github.com/entireio/cli/cmd/entire/cli/trailers"
+	"github.com/entireio/cli/redact"
 
 	"github.com/go-git/go-git/v5"
 	"github.com/go-git/go-git/v5/plumbing"
@@ -238,6 +240,35 @@ var (
 	protectedDirsCache []string
 )
 
+var initRedactionOnce sync.Once
+
+// EnsureRedactionConfigured loads PII redaction settings and configures the
+// redact package. Called once before any checkpoint writes. No-op if PII is
+// not enabled in settings.
+func EnsureRedactionConfigured() {
+	initRedactionOnce.Do(func() {
+		s, err := settings.Load()
+		if err != nil {
+			fmt.Fprintf(os.Stderr, "[entire] Warning: failed to load settings for PII redaction: %v\n", err)
+			return
+		}
+		if s.Redaction == nil || s.Redaction.PII == nil || !s.Redaction.PII.Enabled {
+			return
+		}
+		pii := s.Redaction.PII
+		cfg := redact.PIIConfig{
+			Enabled:        true,
+			Categories:     make(map[redact.PIICategory]bool),
+			CustomPatterns: pii.CustomPatterns,
+		}
+		// Email and phone default to true when PII is enabled; address defaults to false.
+		cfg.Categories[redact.PIIEmail] = pii.Email == nil || *pii.Email
+		cfg.Categories[redact.PIIPhone] = pii.Phone == nil || *pii.Phone
+		cfg.Categories[redact.PIIAddress] = pii.Address != nil && *pii.Address
+		redact.ConfigurePII(cfg)
+	})
+}
+
 // homeRelativePath strips the $HOME/ prefix from an absolute path,
 // returning a home-relative path suitable for persisting in metadata.
 // Returns "" if the path is empty or not under $HOME.

cmd/entire/cli/strategy/manual_commit_condensation.go

@@ -648,6 +648,7 @@ func generateContextFromPrompts(prompts []string) []byte {
 // CondenseSessionByID force-condenses a session by its ID and cleans up.
 // This is used by "entire doctor" to salvage stuck sessions.
 func (s *ManualCommitStrategy) CondenseSessionByID(sessionID string) error {
+	EnsureRedactionConfigured()
 	ctx := logging.WithComponent(context.Background(), "condense-by-id")
 
 	// Load session state

cmd/entire/cli/strategy/manual_commit_git.go

@@ -22,6 +22,8 @@ import (
 // SaveStep saves a checkpoint to the shadow branch.
 // Uses checkpoint.GitStore.WriteTemporary for git operations.
 func (s *ManualCommitStrategy) SaveStep(ctx StepContext) error {
+	EnsureRedactionConfigured()
+
 	repo, err := OpenRepository()
 	if err != nil {
 		return fmt.Errorf("failed to open git repository: %w", err)
@@ -166,6 +168,7 @@ func (s *ManualCommitStrategy) SaveStep(ctx StepContext) error {
 // SaveTaskStep saves a task step checkpoint to the shadow branch.
 // Uses checkpoint.GitStore.WriteTemporaryTask for git operations.
 func (s *ManualCommitStrategy) SaveTaskStep(ctx TaskStepContext) error {
+	EnsureRedactionConfigured()
 	repo, err := OpenRepository()
 	if err != nil {
 		return fmt.Errorf("failed to open git repository: %w", err)

cmd/entire/cli/strategy/manual_commit_hooks.go

@@ -550,6 +550,8 @@ func (h *postCommitActionHandler) HandleWarnStaleSession(_ *session.State) error
 //
 //nolint:unparam // error return required by interface but hooks must return nil
 func (s *ManualCommitStrategy) PostCommit() error {
+	EnsureRedactionConfigured()
+
 	logCtx := logging.WithComponent(context.Background(), "checkpoint")
 
 	repo, err := OpenRepository()