diff --git a/tools/thothctl/internal/pi/update.go b/tools/thothctl/internal/pi/update.go
index 4ce191a7..50b3826d 100644
--- a/tools/thothctl/internal/pi/update.go
+++ b/tools/thothctl/internal/pi/update.go
@@ -114,11 +114,7 @@ func updateWithHooks(ctx context.Context, runner Runner, request Request, hooks
 		}
 		if clearErr := setMaintenance(context.Background(), runner, false); clearErr != nil {
 			result = Result{Phase: PhaseFailed, StatePath: request.StatePath}
-			if retErr == nil {
-				retErr = errors.New("maintenance admission gate could not be cleared: recovery required")
-			} else {
-				retErr = fmt.Errorf("%w; maintenance admission gate could not be cleared: recovery required", retErr)
-			}
+			retErr = errors.Join(retErr, fmt.Errorf("maintenance admission gate could not be cleared: %w", clearErr))
 		}
 	}()
 
@@ -297,11 +293,7 @@ func rollbackWithHooks(ctx context.Context, runner Runner, statePath string, con
 		}
 		if clearErr := setMaintenance(context.Background(), runner, false); clearErr != nil {
 			result = Result{Phase: PhaseFailed, StatePath: statePath}
-			if retErr == nil {
-				retErr = errors.New("maintenance admission gate could not be cleared: recovery required")
-			} else {
-				retErr = fmt.Errorf("%w; maintenance admission gate could not be cleared: recovery required", retErr)
-			}
+			retErr = errors.Join(retErr, fmt.Errorf("maintenance admission gate could not be cleared: %w", clearErr))
 		}
 	}()
 	if maintenanceErr == nil {
@@ -481,7 +473,9 @@ func setMaintenance(ctx context.Context, runner Runner, enabled bool) error {
 	// reading the durable gate state before deciding that operator recovery is required.
 	observed, statusErr := MaintenanceStatus(ctx, runner)
 	if statusErr == nil && observed.Active == enabled && observed.Admissions == 0 {
-		if observed.RecoveryRequired {
+		// curl exit 22 means the server explicitly rejected the POST. A matching marker after
+		// that rejection selects the safest state, but cannot prove the failed write was durable.
+		if observed.RecoveryRequired || result.ExitCode == 22 {
 			return recoveryRequired("maintenance durability was explicitly not acknowledged", err)
 		}
 		return nil
diff --git a/tools/thothctl/internal/pi/update_test.go b/tools/thothctl/internal/pi/update_test.go
index 3f3391ce..e21dc94a 100644
--- a/tools/thothctl/internal/pi/update_test.go
+++ b/tools/thothctl/internal/pi/update_test.go
@@ -209,6 +209,62 @@ func TestMaintenanceReconciliationDoesNotMaskExplicitDurabilityFailure(t *testin
 	}
 }
 
+func TestMaintenanceReconciliationRequiresDurabilityProofAfterExplicitPOSTFailure(t *testing.T) {
+	fake := newFakeRunner()
+	fake.fail = "maintenance-activate-durability-without-status-flag"
+
+	err := setMaintenance(context.Background(), fake, true)
+
+	var recovery *RecoveryRequiredError
+	if err == nil || !errors.As(err, &recovery) || !recovery.RecoveryRequired() {
+		t.Fatalf("maintenance error = %v; want typed recovery-required result", err)
+	}
+	if !fake.maintenance {
+		t.Fatal("safe marker state was not retained after activation durability failure")
+	}
+}
+
+func TestSuccessfulLifecycleCommandsPreserveTypedRecoveryErrorFromMaintenanceCleanup(t *testing.T) {
+	for _, operation := range []string{"update", "rollback"} {
+		t.Run(operation, func(t *testing.T) {
+			fake := newFakeRunner()
+			statePath := filepath.Join(t.TempDir(), "state.json")
+			if operation == "rollback" {
+				if _, err := Update(context.Background(), fake, Request{
+					StatePath: statePath,
+					Version:   "0.81.0",
+					Source:    BuildSource,
+					Confirm:   true,
+				}); err != nil {
+					t.Fatal(err)
+				}
+			}
+			fake.failDeactivationDurability = true
+
+			var result Result
+			var err error
+			if operation == "update" {
+				result, err = Update(context.Background(), fake, Request{
+					StatePath: statePath,
+					Version:   "0.81.0",
+					Source:    BuildSource,
+					Confirm:   true,
+				})
+			} else {
+				result, err = Rollback(context.Background(), fake, statePath, true)
+			}
+
+			var recovery *RecoveryRequiredError
+			if err == nil || !errors.As(err, &recovery) || !recovery.RecoveryRequired() {
+				t.Fatalf("%s error = %v; want typed recovery-required result", operation, err)
+			}
+			if result.Phase != PhaseFailed {
+				t.Fatalf("%s phase = %q, want %q", operation, result.Phase, PhaseFailed)
+			}
+		})
+	}
+}
+
 func TestCompensationReactivatesMaintenanceAndRescansBeforeRollback(t *testing.T) {
 	fake := newFakeRunner()
 	fake.fail = "version"
@@ -742,6 +798,8 @@ type fakeRunner struct {
 	execFailuresWhileStopped      int
 	maintenanceHelperImages       []string
 	maintenanceClearImages        []string
+	failDeactivationDurability    bool
+	deactivationFailed            bool
 	restoredProofComplete         bool
 	candidateVersion              string
 	candidateExpectedVersion      string
@@ -822,7 +880,7 @@ func (f *fakeRunner) Run(_ context.Context, args []string, _ io.Reader) (compose
 		return compose.Result{Stdout: `[{"Type":"volume","Name":"settings","Source":"settings","Destination":"/data/settings","RW":true},{"Type":"volume","Name":"pi-state","Source":"pi-state","Destination":"/home/thoth/.pi","RW":true},{"Type":"volume","Name":"sessions","Source":"sessions","Destination":"/data/sessions","RW":true},{"Type":"volume","Name":"workspace-registry","Source":"workspace-registry","Destination":"/data/workspace-registry","RW":true}]`}, nil
 	case strings.Contains(call, "/internal/maintenance/activate"):
 		f.maintenance = true
-		if f.fail == "maintenance-activate-durability" {
+		if f.fail == "maintenance-activate-durability" || f.fail == "maintenance-activate-durability-without-status-flag" {
 			return compose.Result{ExitCode: 22}, errors.New("maintenance activation durability was not acknowledged")
 		}
 		if f.lostMaintenanceResponse == "activate" {
@@ -836,6 +894,10 @@ func (f *fakeRunner) Run(_ context.Context, args []string, _ io.Reader) (compose
 		}
 		f.maintenance = false
 		f.maintenanceClearImages = append(f.maintenanceClearImages, f.currentImage)
+		if f.failDeactivationDurability {
+			f.deactivationFailed = true
+			return compose.Result{ExitCode: 22}, errors.New("maintenance deactivation durability was not acknowledged")
+		}
 		if f.lostMaintenanceResponse == "deactivate" {
 			f.lostMaintenanceResponse = ""
 			return compose.Result{ExitCode: 52}, errors.New("lost deactivation response")
@@ -845,6 +907,9 @@ func (f *fakeRunner) Run(_ context.Context, args []string, _ io.Reader) (compose
 		if f.fail == "maintenance-activate-durability" {
 			return compose.Result{Stdout: fmt.Sprintf(`{"active":%t,"admissions":0,"recoveryRequired":true}`, f.maintenance)}, nil
 		}
+		if f.deactivationFailed {
+			return compose.Result{Stdout: fmt.Sprintf(`{"active":%t,"admissions":0,"recoveryRequired":true}`, f.maintenance)}, nil
+		}
 		return compose.Result{Stdout: fmt.Sprintf(`{"active":%t,"admissions":0}`, f.maintenance)}, nil
 	case strings.Contains(call, "/sessions?scope=all"):
 		if f.sessionsWire != "" {