diff --git a/server/src/__tests__/health.test.ts b/server/src/__tests__/health.test.ts
index 69449e1f6e..ed95872338 100644
--- a/server/src/__tests__/health.test.ts
+++ b/server/src/__tests__/health.test.ts
@@ -68,6 +68,7 @@ describe("GET /health", () => {
 
   afterEach(() => {
     vi.restoreAllMocks();
+    vi.unstubAllEnvs();
   });
   it("returns 200 with status ok", async () => {
     const app = createApp();
@@ -425,4 +426,77 @@ describe("GET /health", () => {
       serverInfo: testServerInfo,
     });
   });
+
+  it("reports bootstrap_pending in authenticated mode when no instance admin exists", async () => {
+    const { healthRoutes } = await import("../routes/health.js");
+    const db = {
+      execute: vi.fn().mockResolvedValue([{ "?column?": 1 }]),
+      select: vi.fn(() => ({
+        from: vi.fn(() => ({
+          where: vi.fn().mockResolvedValue([{ count: 0 }]),
+        })),
+      })),
+    } as unknown as Db;
+    const app = express();
+    app.use((req, _res, next) => {
+      (req as any).actor = { type: "none", source: "none" };
+      next();
+    });
+    app.use(
+      "/health",
+      healthRoutes(db, {
+        deploymentMode: "authenticated",
+        deploymentExposure: "public",
+        authReady: true,
+        companyDeletionEnabled: false,
+        serverInfo: testServerInfo,
+      }),
+    );
+
+    const res = await request(app).get("/health");
+
+    expect(res.status).toBe(200);
+    expect(res.body).toMatchObject({
+      status: "ok",
+      bootstrapStatus: "bootstrap_pending",
+      bootstrapInviteActive: false,
+    });
+  });
+
+  it("reports bootstrapStatus ready for cloud-managed instances regardless of instance admin count", async () => {
+    vi.stubEnv("PAPERCLIP_CLOUD_TENANT_SERVER_TOKEN", "test-tenant-server-token");
+    const { healthRoutes } = await import("../routes/health.js");
+    const db = {
+      execute: vi.fn().mockResolvedValue([{ "?column?": 1 }]),
+      select: vi.fn(() => ({
+        from: vi.fn(() => ({
+          where: vi.fn().mockResolvedValue([{ count: 0 }]),
+        })),
+      })),
+    } as unknown as Db;
+    const app = express();
+    app.use((req, _res, next) => {
+      (req as any).actor = { type: "none", source: "none" };
+      next();
+    });
+    app.use(
+      "/health",
+      healthRoutes(db, {
+        deploymentMode: "authenticated",
+        deploymentExposure: "public",
+        authReady: true,
+        companyDeletionEnabled: false,
+        serverInfo: testServerInfo,
+      }),
+    );
+
+    const res = await request(app).get("/health");
+
+    expect(res.status).toBe(200);
+    expect(res.body).toMatchObject({
+      status: "ok",
+      bootstrapStatus: "ready",
+      bootstrapInviteActive: false,
+    });
+  });
 });
diff --git a/server/src/middleware/auth.ts b/server/src/middleware/auth.ts
index 7b68a395ed..5a60ccee90 100644
--- a/server/src/middleware/auth.ts
+++ b/server/src/middleware/auth.ts
@@ -375,6 +375,19 @@ export function actorMiddleware(db: Db, opts: ActorMiddlewareOptions): RequestHa
   };
 }
 
+/**
+ * Whether this instance is managed by a Paperclip Cloud control plane.
+ * When the tenant server token is configured, the control plane owns the
+ * user/identity lifecycle for this instance: users arrive through trusted
+ * headers (resolveCloudTenantActor) and are deliberately never granted
+ * instance_admin. Surfaces that assume a self-hosted operator will claim
+ * the instance (e.g. the first-admin bootstrap gate) should treat a
+ * cloud-managed instance as already set up.
+ */
+export function isCloudManagedInstance(): boolean {
+  return Boolean(process.env.PAPERCLIP_CLOUD_TENANT_SERVER_TOKEN?.trim());
+}
+
 export async function resolveCloudTenantActor(db: Db, req: Request): Promise<Express.Request["actor"] | null> {
   const expectedToken = process.env.PAPERCLIP_CLOUD_TENANT_SERVER_TOKEN?.trim();
   if (!expectedToken) return null;
diff --git a/server/src/routes/health.ts b/server/src/routes/health.ts
index fef83f7ad9..760e3e11da 100644
--- a/server/src/routes/health.ts
+++ b/server/src/routes/health.ts
@@ -5,6 +5,7 @@ import { and, count, eq, gt, inArray, isNull, sql } from "drizzle-orm";
 import { heartbeatRuns, instanceUserRoles, invites } from "@paperclipai/db";
 import type { DeploymentExposure, DeploymentMode } from "@paperclipai/shared";
 import { readPersistedDevServerStatus, toDevServerHealthStatus, writeDevServerRestartRequest } from "../dev-server-status.js";
+import { isCloudManagedInstance } from "../middleware/auth.js";
 import { logger } from "../middleware/logger.js";
 import { getServerInfoSnapshot, type ServerInfoSnapshot } from "../server-info.js";
 import {
@@ -148,7 +149,13 @@ export function healthRoutes(
 
     let bootstrapStatus: "ready" | "bootstrap_pending" = "ready";
     let bootstrapInviteActive = false;
-    if (opts.deploymentMode === "authenticated") {
+    // Cloud-managed instances have no first-admin concept: the control
+    // plane owns identity and its trusted-header users are deliberately
+    // never instance_admin, so the role-count gate below would report
+    // bootstrap_pending forever and lock every managed tenant out at the
+    // claim screen. Self-hosted deployments (no tenant server token) are
+    // unaffected.
+    if (opts.deploymentMode === "authenticated" && !isCloudManagedInstance()) {
       const roleCount = await db
         .select({ count: count() })
         .from(instanceUserRoles)