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/doctor.go

@@ -38,6 +38,9 @@ For each stuck session, you can choose to:
 
 Use --force to condense all fixable sessions without prompting.  Sessions that can't
 be condensed will be discarded.`,
+		PreRun: func(_ *cobra.Command, _ []string) {
+			strategy.EnsureRedactionConfigured()
+		},
 		RunE: func(cmd *cobra.Command, _ []string) error {
 			return runSessionsFix(cmd, forceFlag)
 		},

cmd/entire/cli/hooks_git_cmd.go

@@ -81,6 +81,10 @@ func initHookLogging() func() {
 		// Init failed - logging will use stderr fallback
 		return func() {}
 	}
+
+	// Configure PII redaction once at startup (reads settings, no-op if disabled).
+	strategy.EnsureRedactionConfigured()
+
 	return logging.Close
 }
 

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 +222,84 @@ func mergeJSON(settings *EntireSettings, data []byte) error {
 		settings.Telemetry = &t
 	}
 
+	// Merge redaction sub-fields if present (field-level, not wholesale replace).
+	if redactionRaw, ok := raw["redaction"]; ok {
+		if settings.Redaction == nil {
+			settings.Redaction = &RedactionSettings{}
+		}
+		if err := mergeRedaction(settings.Redaction, redactionRaw); err != nil {
+			return fmt.Errorf("parsing redaction field: %w", err)
+		}
+	}
+
+	return nil
+}
+
+// mergeRedaction merges redaction overrides into existing RedactionSettings.
+// Only fields present in the override JSON are applied.
+func mergeRedaction(dst *RedactionSettings, data json.RawMessage) error {
+	var raw map[string]json.RawMessage
+	if err := json.Unmarshal(data, &raw); err != nil {
+		return fmt.Errorf("parsing redaction: %w", err)
+	}
+	if piiRaw, ok := raw["pii"]; ok {
+		if dst.PII == nil {
+			dst.PII = &PIISettings{}
+		}
+		if err := mergePIISettings(dst.PII, piiRaw); err != nil {
+			return err
+		}
+	}
+	return nil
+}
+
+// mergePIISettings merges PII overrides into existing PIISettings.
+// Only fields present in the override JSON are applied; missing fields
+// are preserved from the base settings.
+func mergePIISettings(dst *PIISettings, data json.RawMessage) error {
+	var raw map[string]json.RawMessage
+	if err := json.Unmarshal(data, &raw); err != nil {
+		return fmt.Errorf("parsing pii: %w", err)
+	}
+	if v, ok := raw["enabled"]; ok {
+		if err := json.Unmarshal(v, &dst.Enabled); err != nil {
+			return fmt.Errorf("parsing pii.enabled: %w", err)
+		}
+	}
+	if v, ok := raw["email"]; ok {
+		var b bool
+		if err := json.Unmarshal(v, &b); err != nil {
+			return fmt.Errorf("parsing pii.email: %w", err)
+		}
+		dst.Email = &b
+	}
+	if v, ok := raw["phone"]; ok {
+		var b bool
+		if err := json.Unmarshal(v, &b); err != nil {
+			return fmt.Errorf("parsing pii.phone: %w", err)
+		}
+		dst.Phone = &b
+	}
+	if v, ok := raw["address"]; ok {
+		var b bool
+		if err := json.Unmarshal(v, &b); err != nil {
+			return fmt.Errorf("parsing pii.address: %w", err)
+		}
+		dst.Address = &b
+	}
+	if v, ok := raw["custom_patterns"]; ok {
+		var cp map[string]string
+		if err := json.Unmarshal(v, &cp); err != nil {
+			return fmt.Errorf("parsing pii.custom_patterns: %w", err)
+		}
+		if dst.CustomPatterns == nil {
+			dst.CustomPatterns = cp
+		} else {
+			for k, val := range cp {
+				dst.CustomPatterns[k] = val
+			}
+		}
+	}
 	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 +151,121 @@ 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)
+	}
+}
+
+func TestLoad_LocalMergesRedactionSubfields(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: PII enabled with email=true, phone=true
+	baseContent := `{"strategy":"manual-commit","redaction":{"pii":{"enabled":true,"email":true,"phone":true}}}`
+	if err := os.WriteFile(filepath.Join(entireDir, "settings.json"), []byte(baseContent), 0644); err != nil {
+		t.Fatalf("failed to write settings file: %v", err)
+	}
+
+	// Local: adds custom_patterns only — should NOT erase email/phone from base
+	localContent := `{"redaction":{"pii":{"enabled":true,"custom_patterns":{"ssn":"\\d{3}-\\d{2}-\\d{4}"}}}}`
+	if err := os.WriteFile(filepath.Join(entireDir, "settings.local.json"), []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")
+	}
+	// email and phone from base should survive local merge
+	if settings.Redaction.PII.Email == nil || !*settings.Redaction.PII.Email {
+		t.Error("expected email=true from base to survive local merge")
+	}
+	if settings.Redaction.PII.Phone == nil || !*settings.Redaction.PII.Phone {
+		t.Error("expected phone=true from base to survive local merge")
+	}
+	// custom_patterns from local should be present
+	if settings.Redaction.PII.CustomPatterns == nil {
+		t.Fatal("expected custom_patterns from local to be present")
+	}
+	if _, ok := settings.Redaction.PII.CustomPatterns["ssn"]; !ok {
+		t.Error("expected ssn pattern from local override")
+	}
+}
+
 // 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/common.go

@@ -5,6 +5,7 @@ import (
 	"encoding/json"
 	"errors"
 	"fmt"
+	"log/slog"
 	"os"
 	"os/exec"
 	"path/filepath"
@@ -16,8 +17,11 @@ import (
 	"github.com/entireio/cli/cmd/entire/cli/agent"
 	"github.com/entireio/cli/cmd/entire/cli/checkpoint"
 	"github.com/entireio/cli/cmd/entire/cli/checkpoint/id"
+	"github.com/entireio/cli/cmd/entire/cli/logging"
 	"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 +242,37 @@ var (
 	protectedDirsCache []string
 )
 
+var initRedactionOnce sync.Once
+
+// EnsureRedactionConfigured loads PII redaction settings and configures the
+// redact package. No-op if PII is not enabled in settings.
+// Must be called at each process entry point before checkpoint writes
+// (e.g., hook PersistentPreRunE, doctor PreRun).
+func EnsureRedactionConfigured() {
+	initRedactionOnce.Do(func() {
+		s, err := settings.Load()
+		if err != nil {
+			logCtx := logging.WithComponent(context.Background(), "redaction")
+			logging.Warn(logCtx, "failed to load settings for PII redaction", slog.String("error", err.Error()))
+			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)
+	})
+}
+
 // isSpecificAgentType returns true if the agent type is a known, specific value
 // (not empty and not the generic "Agent" fallback).
 func isSpecificAgentType(t agent.AgentType) bool {