pkg: apply managed DNS mode in the macOS package

cmd/cli/cli.go

@@ -151,6 +151,25 @@ func isMobile() bool {
 	return runtime.GOOS == "android" || runtime.GOOS == "ios"
 }
 
+func updateConfigInterceptMode(cfg *ctrld.Config, mode string) bool {
+	desired := ""
+	switch mode {
+	case "dns", "hard":
+		desired = mode
+	case "off":
+		desired = ""
+	case "":
+		return false
+	default:
+		return false
+	}
+	if cfg.Service.InterceptMode == desired {
+		return false
+	}
+	cfg.Service.InterceptMode = desired
+	return true
+}
+
 // isAndroid reports whether the current OS is Android.
 func isAndroid() bool {
 	return runtime.GOOS == "android"
@@ -367,14 +386,12 @@ func run(appCallback *AppCallback, stopCh chan struct{}) {
 		processLogAndCacheFlags(v, &cfg)
 	}
 
-	// Persist intercept_mode to config when provided via CLI flag on full install.
+	// Keep config and the explicit CLI/service mode in sync. In particular, "off"
-	// This ensures the config file reflects the actual running mode for RMM/MDM visibility.
+	// must clear a previously persisted dns/hard value or the next service start
-	if interceptMode == "dns" || interceptMode == "hard" {
+	// would silently re-enable interception from config.
-		if cfg.Service.InterceptMode != interceptMode {
+	if updateConfigInterceptMode(&cfg, interceptMode) {
-			cfg.Service.InterceptMode = interceptMode
+		updated = true
-			updated = true
+		p.Info().Msgf("writing intercept_mode = %q to config", cfg.Service.InterceptMode)
-			p.Info().Msgf("writing intercept_mode = %q to config", interceptMode)
-		}
 	}
 
 	// Persist firewall_mode to config only when provided via CLI flag.

cmd/cli/commands_service_start.go

@@ -118,21 +118,23 @@ func (sc *ServiceCommand) Start(cmd *cobra.Command, args []string) error {
 	svcExists := serviceConfigFileExists()
 	logger.Debug().Msgf("intercept upgrade check: args=%v interceptOnly=%v svcConfigExists=%v interceptMode=%q", osArgsEarly, interceptOnly, svcExists, interceptMode)
 	if interceptOnly && svcExists {
-		// Remove any existing intercept flags before applying the new value.
+		// Replace any existing split or --intercept-mode=<value> form. Keep an
-		_ = removeServiceFlag("--intercept-mode")
+		// explicit "off" argument so it overrides a previously persisted config
+		// value while the service clears that value on startup.
+		if err := removeServiceFlag("--intercept-mode"); err != nil {
+			logger.Fatal().Err(err).Msg("failed to remove existing intercept mode from service arguments")
+		}
 
 		if interceptMode == "off" {
-			// "off" = remove intercept mode entirely (just the removal above).
+			logger.Notice().Msg("Existing service detected — disabling intercept mode")
-			logger.Notice().Msg("Existing service detected — removing --intercept-mode from service arguments")
 		} else {
-			// Add the new mode value.
 			logger.Notice().Msgf("Existing service detected — appending --intercept-mode %s to service arguments", interceptMode)
-			if err := appendServiceFlag("--intercept-mode"); err != nil {
+		}
-				logger.Fatal().Err(err).Msg("failed to append intercept flag to service arguments")
+		if err := appendServiceFlag("--intercept-mode"); err != nil {
-			}
+			logger.Fatal().Err(err).Msg("failed to append intercept flag to service arguments")
-			if err := appendServiceFlag(interceptMode); err != nil {
+		}
-				logger.Fatal().Err(err).Msg("failed to append intercept mode value to service arguments")
+		if err := appendServiceFlag(interceptMode); err != nil {
-			}
+			logger.Fatal().Err(err).Msg("failed to append intercept mode value to service arguments")
 		}
 
 		// Stop the service if running (bypasses ctrld pin — this is an

cmd/cli/intercept_mode_config_test.go

@@ -0,0 +1,38 @@
+package cli
+
+import (
+	"testing"
+
+	"github.com/Control-D-Inc/ctrld"
+)
+
+func TestUpdateConfigInterceptMode(t *testing.T) {
+	tests := []struct {
+		name        string
+		current     string
+		mode        string
+		want        string
+		wantUpdated bool
+	}{
+		{name: "empty flag preserves config", current: "dns", mode: "", want: "dns"},
+		{name: "dns is persisted", mode: "dns", want: "dns", wantUpdated: true},
+		{name: "hard is persisted", current: "dns", mode: "hard", want: "hard", wantUpdated: true},
+		{name: "off clears persisted mode", current: "dns", mode: "off", want: "", wantUpdated: true},
+		{name: "off is idempotent", mode: "off", want: ""},
+		{name: "invalid flag preserves config", current: "hard", mode: "invalid", want: "hard"},
+	}
+
+	for _, tc := range tests {
+		t.Run(tc.name, func(t *testing.T) {
+			cfg := &ctrld.Config{}
+			cfg.Service.InterceptMode = tc.current
+			updated := updateConfigInterceptMode(cfg, tc.mode)
+			if updated != tc.wantUpdated {
+				t.Fatalf("updateConfigInterceptMode() updated = %v, want %v", updated, tc.wantUpdated)
+			}
+			if cfg.Service.InterceptMode != tc.want {
+				t.Fatalf("service.intercept_mode = %q, want %q", cfg.Service.InterceptMode, tc.want)
+			}
+		})
+	}
+}

cmd/cli/main_test.go

@@ -5,6 +5,7 @@ import (
 	"os"
 	"os/exec"
 	"strings"
+	"sync"
 	"testing"
 
 	"go.uber.org/zap"
@@ -13,7 +14,28 @@ import (
 	"github.com/Control-D-Inc/ctrld"
 )
 
-var logOutput strings.Builder
+// logOutput is the log sink for the whole test binary. Tests share it with any
+// background goroutine the code under test starts (watchdogs, timers), so it
+// must tolerate concurrent writes.
+var logOutput syncBuffer
+
+// syncBuffer is a strings.Builder guarded by a mutex.
+type syncBuffer struct {
+	mu sync.Mutex
+	sb strings.Builder
+}
+
+func (b *syncBuffer) Write(p []byte) (int, error) {
+	b.mu.Lock()
+	defer b.mu.Unlock()
+	return b.sb.Write(p)
+}
+
+func (b *syncBuffer) String() string {
+	b.mu.Lock()
+	defer b.mu.Unlock()
+	return b.sb.String()
+}
 
 // envFakeVersionOutput makes this test binary impersonate a ctrld executable: when
 // set, the process writes the value to stdout and exits without running any test, so

cmd/cli/prog.go

@@ -923,11 +923,12 @@ func (p *prog) setDNS() {
 
 	// Validate and resolve intercept mode.
 	// CLI flag (--intercept-mode) takes priority over config file.
-	// Valid values: "" (off), "dns" (with VPN split routing), "hard" (all DNS through ctrld).
+	// Valid values: "" (use config), "off" (explicitly disable), "dns" (with VPN
+	// split routing), and "hard" (all DNS through ctrld).
 	if interceptMode != "" && !validInterceptMode(interceptMode) {
 		p.Fatal().Msgf("invalid --intercept-mode value %q: must be 'off', 'dns', or 'hard'", interceptMode)
 	}
-	if interceptMode == "" || interceptMode == "off" {
+	if interceptMode == "" {
 		interceptMode = p.configuredInterceptMode()
 		if interceptMode != "" && interceptMode != "off" {
 			p.Info().Msgf("Intercept mode enabled via config (intercept_mode = %q)", interceptMode)

cmd/cli/prog_intercept_fallback_test.go

@@ -132,6 +132,22 @@ func (h *interceptFallbackHarness) run(t *testing.T) {
 	p.setDNS()
 }
 
+func TestSetDNSExplicitOffOverridesConfig(t *testing.T) {
+	h := newInterceptFallbackHarness(t, &ctrld.ListenerConfig{IP: "127.0.0.1", Port: 53})
+	interceptMode = "off"
+	dnsIntercept = false
+	hardIntercept = false
+
+	h.run(t)
+
+	if h.interceptCalls != 0 {
+		t.Fatalf("intercept start called %d time(s), want 0: explicit off must override service.intercept_mode", h.interceptCalls)
+	}
+	if h.installCalls != 1 {
+		t.Fatalf("interface DNS installed %d time(s), want 1", h.installCalls)
+	}
+}
+
 // TestSetDNSRefusesUnreachableFallback is the behaviour test for the reported outage: it
 // drives the real setDNS() lifecycle rather than the classification helper alone.
 //

cmd/cli/service.go

@@ -124,6 +124,11 @@ func (s *systemd) Start() error {
 // This is necessary for running self-upgrade flow.
 func ensureSystemdKillMode(r io.Reader) (opts []*unit.UnitOption, change bool) {
 	opts, err := unit.DeserializeOptions(r)
+	// staticcheck sees only the explicit non-nil sends on the lexer's error
+	// channel, so it reports this comparison as always true. On success the
+	// lexer sends nothing and closes the channel, so the receive yields a nil
+	// error and this branch is not taken.
+	//lint:ignore SA4023 upstream delivers a nil error by closing the channel
 	if err != nil {
 		mainLog.Load().Error().Err(err).Msg("Failed to deserialize options")
 		return

cmd/cli/service_args_darwin.go

@@ -24,19 +24,19 @@ func serviceConfigFileExists() bool {
 // to intercept mode without losing the existing --cd flag and other arguments.
 //
 // On macOS, this modifies the launchd plist at /Library/LaunchDaemons/ctrld.plist
-// using the "defaults" command, which is the standard way to edit plists.
+// using PlistBuddy for exact array reads and writes.
 //
 // The function is idempotent: if the flag already exists, it's a no-op.
 func appendServiceFlag(flag string) error {
 	// Read current ProgramArguments from plist.
-	out, err := exec.Command("defaults", "read", launchdPlistPath, "ProgramArguments").CombinedOutput()
+	out, err := exec.Command("/usr/libexec/PlistBuddy", "-c", "Print :ProgramArguments", launchdPlistPath).CombinedOutput()
 	if err != nil {
 		return fmt.Errorf("failed to read plist ProgramArguments: %w (output: %s)", err, strings.TrimSpace(string(out)))
 	}
 
-	// Check if the flag is already present (idempotent).
+	// Check exact array entries. A substring match can confuse a mode such as "off"
-	args := string(out)
+	// with an unrelated path or argument and leave the flag without its value.
-	if strings.Contains(args, flag) {
+	if serviceArgumentPresent(out, flag) {
 		mainLog.Load().Debug().Msgf("Service flag %q already present in plist, skipping", flag)
 		return nil
 	}
@@ -61,9 +61,8 @@ func verifyServiceRegistration() error {
 	return nil
 }
 
-// removeServiceFlag removes a CLI flag (and its value, if the next argument is not
+// removeServiceFlag removes both "--flag value" and "--flag=value" forms from the
-// a flag) from the installed service's launch arguments. For example, removing
+// installed service's launch arguments.
-// "--intercept-mode" also removes the following "dns" or "hard" value argument.
 //
 // The function is idempotent: if the flag doesn't exist, it's a no-op.
 func removeServiceFlag(flag string) error {
@@ -92,22 +91,14 @@ func removeServiceFlag(flag string) error {
 		entries = append(entries, trimmed)
 	}
 
-	index := -1
+	index, hasValue := serviceFlagPosition(entries, flag)
-	for i, entry := range entries {
-		if entry == flag {
-			index = i
-			break
-		}
-	}
 
 	if index < 0 {
 		mainLog.Load().Debug().Msgf("Service flag %q not present in plist, skipping removal", flag)
 		return nil
 	}
 
-	// Check if the next entry is a value (not a flag). If so, delete it first
+	// Delete a separate value first. An inline --flag=value entry is one array item.
-	// (deleting by index shifts subsequent entries down, so delete value before flag).
-	hasValue := index+1 < len(entries) && !strings.HasPrefix(entries[index+1], "-")
 	if hasValue {
 		delVal := exec.Command(
 			"/usr/libexec/PlistBuddy",
@@ -132,3 +123,24 @@ func removeServiceFlag(flag string) error {
 	mainLog.Load().Info().Msgf("Removed %q from service launch arguments", flag)
 	return nil
 }
+
+func serviceArgumentPresent(out []byte, argument string) bool {
+	for _, line := range strings.Split(string(out), "\n") {
+		if strings.TrimSpace(line) == argument {
+			return true
+		}
+	}
+	return false
+}
+
+func serviceFlagPosition(entries []string, flag string) (index int, hasValue bool) {
+	for i, entry := range entries {
+		switch {
+		case entry == flag:
+			return i, i+1 < len(entries) && !strings.HasPrefix(entries[i+1], "-")
+		case strings.HasPrefix(entry, flag+"="):
+			return i, false
+		}
+	}
+	return -1, false
+}

cmd/cli/service_args_darwin_test.go

@@ -0,0 +1,58 @@
+//go:build darwin
+
+package cli
+
+import "testing"
+
+func TestServiceArgumentPresent(t *testing.T) {
+	out := []byte("Array {\n    /usr/local/bin/ctrld\n    run\n    --config=/Users/officer/ctrld.toml\n    --intercept-mode=dns\n}\n")
+	if !serviceArgumentPresent(out, "--intercept-mode=dns") {
+		t.Fatal("exact inline argument was not found")
+	}
+	if serviceArgumentPresent(out, "--intercept-mode") {
+		t.Fatal("inline flag was mistaken for a separate flag argument")
+	}
+	if serviceArgumentPresent(out, "off") {
+		t.Fatal("substring in an unrelated path was mistaken for the off argument")
+	}
+}
+
+func TestServiceFlagPosition(t *testing.T) {
+	tests := []struct {
+		name         string
+		entries      []string
+		wantIndex    int
+		wantHasValue bool
+	}{
+		{
+			name:         "split form",
+			entries:      []string{"run", "--cd=uid", "--intercept-mode", "dns"},
+			wantIndex:    2,
+			wantHasValue: true,
+		},
+		{
+			name:      "inline form",
+			entries:   []string{"run", "--cd=uid", "--intercept-mode=dns"},
+			wantIndex: 2,
+		},
+		{
+			name:      "flag followed by another flag",
+			entries:   []string{"run", "--intercept-mode", "--config=/etc/ctrld.toml"},
+			wantIndex: 1,
+		},
+		{
+			name:      "absent",
+			entries:   []string{"run", "--cd=uid"},
+			wantIndex: -1,
+		},
+	}
+
+	for _, tc := range tests {
+		t.Run(tc.name, func(t *testing.T) {
+			index, hasValue := serviceFlagPosition(tc.entries, "--intercept-mode")
+			if index != tc.wantIndex || hasValue != tc.wantHasValue {
+				t.Fatalf("serviceFlagPosition() = (%d, %v), want (%d, %v)", index, hasValue, tc.wantIndex, tc.wantHasValue)
+			}
+		})
+	}
+}

cmd/cli/service_args_others.go

@@ -3,10 +3,14 @@
 package cli
 
 import (
-	"fmt"
+	"errors"
 	"os"
 )
 
+// errServiceFlagsUnsupported is returned by the service-argument helpers on
+// platforms that do not store service arguments in a file ctrld can rewrite.
+var errServiceFlagsUnsupported = errors.New("modifying service flags is not supported on this platform; use intercept_mode in config instead")
+
 // serviceConfigFileExists checks common service config file locations on Linux.
 func serviceConfigFileExists() bool {
 	// systemd unit file
@@ -24,7 +28,7 @@ func serviceConfigFileExists() bool {
 // Linux services (systemd) store args in unit files; intercept mode
 // should be set via the config file (intercept_mode) on these platforms.
 func appendServiceFlag(flag string) error {
-	return fmt.Errorf("appending service flags is not supported on this platform; use intercept_mode in config instead")
+	return errServiceFlagsUnsupported
 }
 
 // verifyServiceRegistration is a no-op on this platform.
@@ -34,5 +38,5 @@ func verifyServiceRegistration() error {
 
 // removeServiceFlag is not yet implemented on this platform.
 func removeServiceFlag(flag string) error {
-	return fmt.Errorf("removing service flags is not supported on this platform; use intercept_mode in config instead")
+	return errServiceFlagsUnsupported
 }

cmd/cli/service_args_windows.go

@@ -47,8 +47,9 @@ func appendServiceFlag(flag string) error {
 		return fmt.Errorf("failed to read service config: %w", err)
 	}
 
-	// Check if flag already present (idempotent).
+	// Check exact arguments so a short mode such as "off" is not confused with
-	if strings.Contains(config.BinaryPathName, flag) {
+	// an unrelated path or value.
+	if binaryPathArgumentPresent(config.BinaryPathName, flag) {
 		mainLog.Load().Debug().Msgf("Service flag %q already present in BinPath, skipping", flag)
 		return nil
 	}
@@ -103,9 +104,8 @@ func verifyServiceRegistration() error {
 	return nil
 }
 
-// removeServiceFlag removes a CLI flag (and its value, if present) from the installed
+// removeServiceFlag removes both "--flag value" and "--flag=value" forms from the
-// Windows service's BinPath. For example, removing "--intercept-mode" also removes
+// installed Windows service's BinPath. The function is idempotent.
-// the following "dns" or "hard" value. The function is idempotent.
 func removeServiceFlag(flag string) error {
 	m, err := mgr.Connect()
 	if err != nil {
@@ -124,25 +124,12 @@ func removeServiceFlag(flag string) error {
 		return fmt.Errorf("failed to read service config: %w", err)
 	}
 
-	if !strings.Contains(config.BinaryPathName, flag) {
+	updatedPath, removed := removeBinaryPathFlag(config.BinaryPathName, flag)
+	if !removed {
 		mainLog.Load().Debug().Msgf("Service flag %q not present in BinPath, skipping removal", flag)
 		return nil
 	}
-
+	config.BinaryPathName = updatedPath
-	// Split BinPath into parts, find and remove the flag + its value (if any).
-	parts := strings.Fields(config.BinaryPathName)
-	var newParts []string
-	for i := 0; i < len(parts); i++ {
-		if parts[i] == flag {
-			// Skip the flag. Also skip the next part if it's a value (not a flag).
-			if i+1 < len(parts) && !strings.HasPrefix(parts[i+1], "-") {
-				i++ // skip value too
-			}
-			continue
-		}
-		newParts = append(newParts, parts[i])
-	}
-	config.BinaryPathName = strings.Join(newParts, " ")
 
 	if err := s.UpdateConfig(config); err != nil {
 		return fmt.Errorf("failed to update service config: %w", err)
@@ -151,3 +138,32 @@ func removeServiceFlag(flag string) error {
 	mainLog.Load().Info().Msgf("Removed %q from service BinPath", flag)
 	return nil
 }
+
+func binaryPathArgumentPresent(binaryPath, argument string) bool {
+	for _, part := range strings.Fields(binaryPath) {
+		if part == argument {
+			return true
+		}
+	}
+	return false
+}
+
+func removeBinaryPathFlag(binaryPath, flag string) (string, bool) {
+	parts := strings.Fields(binaryPath)
+	newParts := make([]string, 0, len(parts))
+	removed := false
+	for i := 0; i < len(parts); i++ {
+		switch {
+		case parts[i] == flag:
+			removed = true
+			if i+1 < len(parts) && !strings.HasPrefix(parts[i+1], "-") {
+				i++
+			}
+		case strings.HasPrefix(parts[i], flag+"="):
+			removed = true
+		default:
+			newParts = append(newParts, parts[i])
+		}
+	}
+	return strings.Join(newParts, " "), removed
+}

cmd/cli/service_args_windows_test.go

@@ -0,0 +1,54 @@
+//go:build windows
+
+package cli
+
+import "testing"
+
+func TestBinaryPathArgumentPresent(t *testing.T) {
+	path := `C:\ControlD\ctrld.exe run --config=C:\Users\officer\ctrld.toml --intercept-mode=dns`
+	if !binaryPathArgumentPresent(path, "--intercept-mode=dns") {
+		t.Fatal("exact inline argument was not found")
+	}
+	if binaryPathArgumentPresent(path, "--intercept-mode") {
+		t.Fatal("inline flag was mistaken for a separate flag argument")
+	}
+	if binaryPathArgumentPresent(path, "off") {
+		t.Fatal("substring in an unrelated path was mistaken for the off argument")
+	}
+}
+
+func TestRemoveBinaryPathFlag(t *testing.T) {
+	tests := []struct {
+		name        string
+		binaryPath  string
+		wantPath    string
+		wantRemoved bool
+	}{
+		{
+			name:        "split form",
+			binaryPath:  `ctrld.exe run --cd=uid --intercept-mode dns --config=ctrld.toml`,
+			wantPath:    `ctrld.exe run --cd=uid --config=ctrld.toml`,
+			wantRemoved: true,
+		},
+		{
+			name:        "inline form",
+			binaryPath:  `ctrld.exe run --cd=uid --intercept-mode=dns --config=ctrld.toml`,
+			wantPath:    `ctrld.exe run --cd=uid --config=ctrld.toml`,
+			wantRemoved: true,
+		},
+		{
+			name:       "absent",
+			binaryPath: `ctrld.exe run --cd=uid`,
+			wantPath:   `ctrld.exe run --cd=uid`,
+		},
+	}
+
+	for _, tc := range tests {
+		t.Run(tc.name, func(t *testing.T) {
+			path, removed := removeBinaryPathFlag(tc.binaryPath, "--intercept-mode")
+			if path != tc.wantPath || removed != tc.wantRemoved {
+				t.Fatalf("removeBinaryPathFlag() = (%q, %v), want (%q, %v)", path, removed, tc.wantPath, tc.wantRemoved)
+			}
+		})
+	}
+}

test-scripts/darwin/test-pkg-intercept-mode.sh

@@ -0,0 +1,123 @@
+#!/bin/sh
+set -eu
+
+repo_root=$(CDPATH= cd -- "$(dirname -- "$0")/../.." && pwd)
+postinstall="$repo_root/scripts/pkg/postinstall"
+fixture=$(mktemp -d "${TMPDIR:-/tmp}/ctrld-pkg-intercept.XXXXXX")
+trap 'rm -rf "$fixture"' EXIT HUP INT TERM
+
+bin="$fixture/bin"
+mkdir -p "$bin"
+
+cat >"$bin/defaults" <<'EOF'
+#!/bin/sh
+key=${3:-}
+case "$key" in
+    ProvisionToken)
+        [ "${FAKE_TOKEN_PRESENT:-0}" = "1" ] || exit 1
+        printf '%s\n' "${FAKE_TOKEN:-test-token}"
+        ;;
+    InterceptMode)
+        [ "${FAKE_MODE_PRESENT:-0}" = "1" ] || exit 1
+        printf '%s\n' "${FAKE_MODE:-}"
+        ;;
+    CustomHostname|UseDevEnvironment)
+        exit 1
+        ;;
+    *)
+        exit 1
+        ;;
+esac
+EOF
+
+cat >"$bin/launchctl" <<'EOF'
+#!/bin/sh
+printf 'launchctl %s\n' "$*" >>"$CALLS"
+exit 0
+EOF
+
+cat >"$bin/ctrld" <<'EOF'
+#!/bin/sh
+printf 'ctrld %s\n' "$*" >>"$CALLS"
+case " $* " in
+    *" --cd-org="*) : >"$CTRLD_POSTINSTALL_PLIST" ;;
+esac
+exit 0
+EOF
+
+chmod +x "$bin/defaults" "$bin/launchctl" "$bin/ctrld"
+
+assert_contains() {
+    expected=$1
+    file=$2
+    if ! grep -Fq -- "$expected" "$file"; then
+        printf 'FAIL: expected %s in %s\n' "$expected" "$file" >&2
+        sed -n '1,120p' "$file" >&2
+        exit 1
+    fi
+}
+
+assert_not_contains() {
+    unexpected=$1
+    file=$2
+    if grep -Fq -- "$unexpected" "$file"; then
+        printf 'FAIL: did not expect %s in %s\n' "$unexpected" "$file" >&2
+        sed -n '1,120p' "$file" >&2
+        exit 1
+    fi
+}
+
+run_case() {
+    name=$1
+    existing=$2
+    mode_present=$3
+    mode=$4
+    case_dir="$fixture/$name"
+    mkdir -p "$case_dir"
+    plist="$case_dir/ctrld.plist"
+    prefs="$case_dir/preferences"
+    calls="$case_dir/calls"
+    output="$case_dir/output"
+    : >"$calls"
+    if [ "$existing" = "1" ]; then
+        : >"$plist"
+    fi
+
+    PATH="$bin:$PATH" \
+    CALLS="$calls" \
+    FAKE_TOKEN_PRESENT=1 \
+    FAKE_TOKEN=test-token \
+    FAKE_MODE_PRESENT="$mode_present" \
+    FAKE_MODE="$mode" \
+    CTRLD_POSTINSTALL_PLIST="$plist" \
+    CTRLD_POSTINSTALL_CTRLD="$bin/ctrld" \
+    CTRLD_POSTINSTALL_PREFS="$prefs" \
+    "$postinstall" >"$output" 2>&1
+
+    printf '%s\n' "$case_dir"
+}
+
+case_dir=$(run_case fresh-legacy 0 0 '')
+assert_contains 'ctrld start --cd-org=test-token' "$case_dir/calls"
+assert_not_contains '--intercept-mode' "$case_dir/calls"
+
+case_dir=$(run_case fresh-standard 0 1 standard)
+assert_contains 'ctrld start --cd-org=test-token' "$case_dir/calls"
+assert_not_contains '--intercept-mode' "$case_dir/calls"
+
+case_dir=$(run_case fresh-intercept 0 1 intercept-dns)
+assert_contains 'ctrld start --cd-org=test-token --intercept-mode dns' "$case_dir/calls"
+
+case_dir=$(run_case upgrade-legacy 1 0 '')
+assert_contains 'launchctl load' "$case_dir/calls"
+assert_not_contains 'ctrld start' "$case_dir/calls"
+
+case_dir=$(run_case upgrade-standard 1 1 standard)
+assert_contains 'ctrld start --intercept-mode off' "$case_dir/calls"
+assert_not_contains 'launchctl load' "$case_dir/calls"
+
+case_dir=$(run_case upgrade-intercept 1 1 intercept-dns)
+assert_contains 'ctrld start --intercept-mode dns' "$case_dir/calls"
+assert_not_contains 'launchctl load' "$case_dir/calls"
+
+printf 'PASS: pkg postinstall preserves legacy mode and applies standard/intercept-dns policy\n'