diff --git a/internal/engine/secretspush.go b/internal/engine/secretspush.go
index b00488c6..a7f8caaf 100644
--- a/internal/engine/secretspush.go
+++ b/internal/engine/secretspush.go
@@ -301,6 +301,20 @@ func (e *Engine) currentSecretEngine(ctx context.Context, current string) (*Engi
 	return releaseEngine, nil
 }
 
+// DeployedSecretGeneration reads the active generation against the immutable
+// declaration graph that produced the deployed release. A new project may add
+// or remove secret-consuming workloads; using its graph to inspect the old
+// runtime mistakes that intentional transition for partial live state.
+func (e *Engine) DeployedSecretGeneration(ctx context.Context, releaseID string, composeBytes []byte) (string, error) {
+	releaseEngine, err := e.engineFromReleaseSnapshotFor(ctx, releaseID, "deploy planning")
+	if err != nil {
+		return "", err
+	}
+	graph := releaseEngine.Spec.SecretDeclarationGraph()
+	workloads := affectedLiveSecretWorkloads(releaseEngine.Spec, graph)
+	return app.SecretGenerationFromCompose(composeBytes, workloads)
+}
+
 func (e *Engine) cleanupSecretUploads(ctx context.Context) error {
 	return e.mutateChecked(ctx, "clean abandoned secret uploads", "rm -rf "+q(e.base()+"/.secret-upload-")+"*")
 }
diff --git a/internal/onebox/plan_deploy.go b/internal/onebox/plan_deploy.go
index 97f6ff63..a81fdb68 100644
--- a/internal/onebox/plan_deploy.go
+++ b/internal/onebox/plan_deploy.go
@@ -71,7 +71,7 @@ func (s *Service) PlanDeploy(ctx context.Context, _ PlanDeployRequest) (DeployPl
 	secretGraph := lp.resolved.SecretDeclarationGraph()
 	if len(secretGraph) > 0 {
 		if hostState.CurrentRelease != "" {
-			activeSecretGeneration, err = app.SecretGenerationFromCompose([]byte(liveRedacted), secretGraphWorkloads(secretGraph))
+			activeSecretGeneration, err = e.DeployedSecretGeneration(ctx, hostState.CurrentRelease, []byte(liveRedacted))
 			if err != nil {
 				return DeployPlan{}, fmt.Errorf("read live secret generation: %w", err)
 			}
@@ -230,16 +230,6 @@ func (s *Service) PlanDeploy(ctx context.Context, _ PlanDeployRequest) (DeployPl
 	return plan, nil
 }
 
-func secretGraphWorkloads(graph []app.SecretDeclaration) []string {
-	set := map[string]bool{}
-	for _, declaration := range graph {
-		for _, workload := range declaration.AffectedWorkloads {
-			set[workload] = true
-		}
-	}
-	return sortedNames(set)
-}
-
 func classifyDeployment(steps []OperationStep, currentRelease string) (RiskClass, ReversibilityClass, ApprovalClass) {
 	for _, step := range steps {
 		if step.DataEffect == DataEffectDestructive {
diff --git a/internal/onebox/service_test.go b/internal/onebox/service_test.go
index 6fbfbd11..d9029934 100644
--- a/internal/onebox/service_test.go
+++ b/internal/onebox/service_test.go
@@ -210,3 +210,86 @@ func TestPlanDeployRetainsComposeBuildImageForBoundReplay(t *testing.T) {
 		}
 	}
 }
+
+func TestPlanDeployUsesDeployedSecretGraphDuringTransition(t *testing.T) {
+	fakeSops(t)
+	dir := t.TempDir()
+	write := func(name, body string) {
+		t.Helper()
+		if err := os.WriteFile(filepath.Join(dir, name), []byte(body), 0o600); err != nil {
+			t.Fatal(err)
+		}
+	}
+	imageWeb := "ghcr.io/example/web@sha256:" + strings.Repeat("1", 64)
+	imageWorker := "ghcr.io/example/worker@sha256:" + strings.Repeat("2", 64)
+	project := func(workerSecret bool) string {
+		workerEnv := ""
+		if workerSecret {
+			workerEnv = "\n    env_files: [{file: worker.enc.env, provider: sops}]"
+		}
+		return `api_version: onebox.run/v1
+app: demo
+environments:
+  production: {server: deploy@example.invalid}
+workloads:
+  web:
+    role: application
+    image: ` + imageWeb + `
+    strategy: recreate
+    env_files: [{file: web.enc.env, provider: sops}]
+  worker:
+    role: daemon
+    image: ` + imageWorker + workerEnv + `
+deployment: {order: [web, worker]}
+`
+	}
+	write("web.enc.env", "WEB_TOKEN=web\n")
+	write("worker.enc.env", "WORKER_TOKEN=worker\n")
+	write("ob.yml", project(true))
+
+	const oldGeneration = "sg-111111111111111111111111"
+	liveCompose := `services:
+  web:
+    image: ` + imageWeb + `
+    env_file: [.ob-secret-generations/` + oldGeneration + `/.ob-decrypted-sops-web.enc.env]
+    labels: {ob.app: demo, ob.release: R0, ob.workload: web, ob.secret-generation: ` + oldGeneration + `}
+  worker:
+    image: ` + imageWorker + `
+    labels: {ob.app: demo, ob.release: R0, ob.workload: worker}
+`
+	fake := serviceFake()
+	baseDynamic := fake.Dynamic
+	fake.Dynamic = func(command string) (transport.Result, bool) {
+		switch {
+		case strings.Contains(command, "ob.snapshot.yml"):
+			return transport.Result{Stdout: project(false)}, true
+		case strings.Contains(command, "cat ") && strings.Contains(command, "compose.yaml"):
+			return transport.Result{Stdout: liveCompose}, true
+		case strings.Contains(command, "docker ps") && strings.Contains(command, "--format"):
+			return transport.Result{Stdout: "S1|web|R0|Up\nW1|worker|R0|Up\n"}, true
+		default:
+			return baseDynamic(command)
+		}
+	}
+	service := New(Options{
+		ConfigPath: filepath.Join(dir, "ob.yml"),
+		Now:        func() time.Time { return time.Date(2026, 8, 23, 19, 0, 0, 0, time.UTC) },
+		Connect: func(context.Context, transport.Route) (transport.Transport, error) {
+			return fake, nil
+		},
+	})
+	plan, err := service.PlanDeploy(context.Background(), PlanDeployRequest{})
+	if err != nil {
+		t.Fatal(err)
+	}
+	if plan.Artifact.SecretGeneration == "" || plan.Artifact.SecretGeneration == oldGeneration {
+		t.Fatalf("replacement generation = %q", plan.Artifact.SecretGeneration)
+	}
+	for _, secret := range []string{"web.enc.env", "worker.enc.env"} {
+		staged := app.EnvFile{File: secret, Provider: "sops"}.StagedPath()
+		want := app.SecretGenerationPath(plan.Artifact.SecretGeneration, staged)
+		if !strings.Contains(plan.Artifact.RenderedCompose, want) {
+			t.Fatalf("planned runtime does not select %s:\n%s", want, plan.Artifact.RenderedCompose)
+		}
+	}
+}