diff --git a/package-lock.json b/package-lock.json
index aaaf674..26474d0 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -10,31 +10,19 @@
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@@ -1286,10 +1196,10 @@
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@@ -1303,6 +1213,24 @@
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-        "estree-walker": "^3.0.3",
-        "loupe": "^2.3.7",
-        "pretty-format": "^29.7.0"
-      },
-      "funding": {
-        "url": "https://opencollective.com/vitest"
-      }
-    },
-    "packages/claude-plugin/node_modules/assertion-error": {
-      "version": "1.1.0",
-      "resolved": "https://registry.npmjs.org/assertion-error/-/assertion-error-1.1.0.tgz",
-      "integrity": "sha512-jgsaNduz+ndvGyFt3uSuWqvy4lCnIJiovtouQN5JZHOKCS2QuhEdbcQHFhVksz2N2U9hXJo8odG7ETyWlEeuDw==",
-      "dev": true,
-      "license": "MIT",
-      "engines": {
-        "node": "*"
-      }
-    },
-    "packages/claude-plugin/node_modules/chai": {
-      "version": "4.5.0",
-      "resolved": "https://registry.npmjs.org/chai/-/chai-4.5.0.tgz",
-      "integrity": "sha512-RITGBfijLkBddZvnn8jdqoTypxvqbOLYQkGGxXzeFjVHvudaPw0HNFD9x928/eUwYWd2dPCugVqspGALTZZQKw==",
-      "dev": true,
-      "license": "MIT",
-      "dependencies": {
-        "assertion-error": "^1.1.0",
-        "check-error": "^1.0.3",
-        "deep-eql": "^4.1.3",
-        "get-func-name": "^2.0.2",
-        "loupe": "^2.3.6",
-        "pathval": "^1.1.1",
-        "type-detect": "^4.1.0"
-      },
-      "engines": {
-        "node": ">=4"
-      }
-    },
-    "packages/claude-plugin/node_modules/check-error": {
-      "version": "1.0.3",
-      "resolved": "https://registry.npmjs.org/check-error/-/check-error-1.0.3.tgz",
-      "integrity": "sha512-iKEoDYaRmd1mxM90a2OEfWhjsjPpYPuQ+lMYsoxB126+t8fw7ySEO48nmDg5COTjxDI65/Y2OWpeEHk3ZOe8zg==",
-      "dev": true,
-      "license": "MIT",
-      "dependencies": {
-        "get-func-name": "^2.0.2"
-      },
-      "engines": {
-        "node": "*"
-      }
-    },
-    "packages/claude-plugin/node_modules/deep-eql": {
-      "version": "4.1.4",
-      "resolved": "https://registry.npmjs.org/deep-eql/-/deep-eql-4.1.4.tgz",
-      "integrity": "sha512-SUwdGfqdKOwxCPeVYjwSyRpJ7Z+fhpwIAtmCUdZIWZ/YP5R9WAsyuSgpLVDi9bjWoN2LXHNss/dk3urXtdQxGg==",
-      "dev": true,
-      "license": "MIT",
-      "dependencies": {
-        "type-detect": "^4.0.0"
-      },
-      "engines": {
-        "node": ">=6"
-      }
-    },
-    "packages/claude-plugin/node_modules/loupe": {
-      "version": "2.3.7",
-      "resolved": "https://registry.npmjs.org/loupe/-/loupe-2.3.7.tgz",
-      "integrity": "sha512-zSMINGVYkdpYSOBmLi0D1Uo7JU9nVdQKrHxC8eYlV+9YKK9WePqAlL7lSlorG/U2Fw1w0hTBmaa/jrQ3UbPHtA==",
-      "dev": true,
-      "license": "MIT",
-      "dependencies": {
-        "get-func-name": "^2.0.1"
-      }
-    },
-    "packages/claude-plugin/node_modules/p-limit": {
-      "version": "5.0.0",
-      "resolved": "https://registry.npmjs.org/p-limit/-/p-limit-5.0.0.tgz",
-      "integrity": "sha512-/Eaoq+QyLSiXQ4lyYV23f14mZRQcXnxfHrN0vCai+ak9G0pp9iEQukIIZq5NccEvwRB8PUnZT0KsOoDCINS1qQ==",
-      "dev": true,
-      "license": "MIT",
-      "dependencies": {
-        "yocto-queue": "^1.0.0"
-      },
-      "engines": {
-        "node": ">=18"
-      },
-      "funding": {
-        "url": "https://github.com/sponsors/sindresorhus"
-      }
-    },
-    "packages/claude-plugin/node_modules/pathe": {
-      "version": "1.1.2",
-      "resolved": "https://registry.npmjs.org/pathe/-/pathe-1.1.2.tgz",
-      "integrity": "sha512-whLdWMYL2TwI08hn8/ZqAbrVemu0LNaNNJZX73O6qaIdCTfXutsLhMkjdENX0qhsQ9uIimo4/aQOmXkoon2nDQ==",
-      "dev": true,
-      "license": "MIT"
-    },
-    "packages/claude-plugin/node_modules/pathval": {
-      "version": "1.1.1",
-      "resolved": "https://registry.npmjs.org/pathval/-/pathval-1.1.1.tgz",
-      "integrity": "sha512-Dp6zGqpTdETdR63lehJYPeIOqpiNBNtc7BpWSLrOje7UaIsE5aY92r/AunQA7rsXvet3lrJ3JnZX29UPTKXyKQ==",
-      "dev": true,
-      "license": "MIT",
-      "engines": {
-        "node": "*"
-      }
-    },
-    "packages/claude-plugin/node_modules/tinypool": {
-      "version": "0.8.4",
-      "resolved": "https://registry.npmjs.org/tinypool/-/tinypool-0.8.4.tgz",
-      "integrity": "sha512-i11VH5gS6IFeLY3gMBQ00/MmLncVP7JLXOw1vlgkytLmJK7QnEr7NXf0LBdxfmNPAeyetukOk0bOYrJrFGjYJQ==",
-      "dev": true,
-      "license": "MIT",
-      "engines": {
-        "node": ">=14.0.0"
-      }
-    },
-    "packages/claude-plugin/node_modules/tinyspy": {
-      "version": "2.2.1",
-      "resolved": "https://registry.npmjs.org/tinyspy/-/tinyspy-2.2.1.tgz",
-      "integrity": "sha512-KYad6Vy5VDWV4GH3fjpseMQ/XU2BhIYP7Vzd0LG44qRWm/Yt2WCOTicFdvmgo6gWaqooMQCawTtILVQJupKu7A==",
-      "dev": true,
-      "license": "MIT",
-      "engines": {
-        "node": ">=14.0.0"
+        "vitest": "^4.1.8"
       }
     },
     "packages/claude-plugin/node_modules/typescript": {
@@ -7260,108 +6332,6 @@
         "node": ">=14.17"
       }
     },
-    "packages/claude-plugin/node_modules/vite-node": {
-      "version": "1.6.1",
-      "resolved": "https://registry.npmjs.org/vite-node/-/vite-node-1.6.1.tgz",
-      "integrity": "sha512-YAXkfvGtuTzwWbDSACdJSg4A4DZiAqckWe90Zapc/sEX3XvHcw1NdurM/6od8J207tSDqNbSsgdCacBgvJKFuA==",
-      "dev": true,
-      "license": "MIT",
-      "dependencies": {
-        "cac": "^6.7.14",
-        "debug": "^4.3.4",
-        "pathe": "^1.1.1",
-        "picocolors": "^1.0.0",
-        "vite": "^5.0.0"
-      },
-      "bin": {
-        "vite-node": "vite-node.mjs"
-      },
-      "engines": {
-        "node": "^18.0.0 || >=20.0.0"
-      },
-      "funding": {
-        "url": "https://opencollective.com/vitest"
-      }
-    },
-    "packages/claude-plugin/node_modules/vitest": {
-      "version": "1.6.1",
-      "resolved": "https://registry.npmjs.org/vitest/-/vitest-1.6.1.tgz",
-      "integrity": "sha512-Ljb1cnSJSivGN0LqXd/zmDbWEM0RNNg2t1QW/XUhYl/qPqyu7CsqeWtqQXHVaJsecLPuDoak2oJcZN2QoRIOag==",
-      "dev": true,
-      "license": "MIT",
-      "dependencies": {
-        "@vitest/expect": "1.6.1",
-        "@vitest/runner": "1.6.1",
-        "@vitest/snapshot": "1.6.1",
-        "@vitest/spy": "1.6.1",
-        "@vitest/utils": "1.6.1",
-        "acorn-walk": "^8.3.2",
-        "chai": "^4.3.10",
-        "debug": "^4.3.4",
-        "execa": "^8.0.1",
-        "local-pkg": "^0.5.0",
-        "magic-string": "^0.30.5",
-        "pathe": "^1.1.1",
-        "picocolors": "^1.0.0",
-        "std-env": "^3.5.0",
-        "strip-literal": "^2.0.0",
-        "tinybench": "^2.5.1",
-        "tinypool": "^0.8.3",
-        "vite": "^5.0.0",
-        "vite-node": "1.6.1",
-        "why-is-node-running": "^2.2.2"
-      },
-      "bin": {
-        "vitest": "vitest.mjs"
-      },
-      "engines": {
-        "node": "^18.0.0 || >=20.0.0"
-      },
-      "funding": {
-        "url": "https://opencollective.com/vitest"
-      },
-      "peerDependencies": {
-        "@edge-runtime/vm": "*",
-        "@types/node": "^18.0.0 || >=20.0.0",
-        "@vitest/browser": "1.6.1",
-        "@vitest/ui": "1.6.1",
-        "happy-dom": "*",
-        "jsdom": "*"
-      },
-      "peerDependenciesMeta": {
-        "@edge-runtime/vm": {
-          "optional": true
-        },
-        "@types/node": {
-          "optional": true
-        },
-        "@vitest/browser": {
-          "optional": true
-        },
-        "@vitest/ui": {
-          "optional": true
-        },
-        "happy-dom": {
-          "optional": true
-        },
-        "jsdom": {
-          "optional": true
-        }
-      }
-    },
-    "packages/claude-plugin/node_modules/yocto-queue": {
-      "version": "1.2.2",
-      "resolved": "https://registry.npmjs.org/yocto-queue/-/yocto-queue-1.2.2.tgz",
-      "integrity": "sha512-4LCcse/U2MHZ63HAJVE+v71o7yOdIe4cZ70Wpf8D/IyjDKYQLV5GD46B+hSTjJsvV5PztjvHoU580EftxjDZFQ==",
-      "dev": true,
-      "license": "MIT",
-      "engines": {
-        "node": ">=12.20"
-      },
-      "funding": {
-        "url": "https://github.com/sponsors/sindresorhus"
-      }
-    },
     "packages/mcp-server": {
       "name": "pluginos",
       "version": "0.4.3",
@@ -7378,12 +6348,12 @@
         "@pluginos/shared": "*",
         "@types/adm-zip": "^0.5.8",
         "@types/ws": "^8.5.0",
-        "@vitest/coverage-v8": "^2.1.9",
+        "@vitest/coverage-v8": "^4.1.8",
         "adm-zip": "^0.5.17",
         "tsup": "^8.5.1",
         "tsx": "^4.19.0",
         "typescript": "^5.5.0",
-        "vitest": "^2.1.0"
+        "vitest": "^4.1.8"
       },
       "engines": {
         "node": ">=18"
@@ -7407,9 +6377,9 @@
       "name": "@pluginos/shared",
       "version": "0.4.3",
       "devDependencies": {
-        "@vitest/coverage-v8": "^2.1.9",
+        "@vitest/coverage-v8": "^4.1.8",
         "typescript": "^5.5.0",
-        "vitest": "^2.1.0"
+        "vitest": "^4.1.8"
       }
     },
     "packages/shared/node_modules/typescript": {
diff --git a/package.json b/package.json
index c25e5e3..5eea0b2 100644
--- a/package.json
+++ b/package.json
@@ -22,14 +22,18 @@
   },
   "devDependencies": {
     "@eslint/js": "^10.0.1",
+    "@vitest/coverage-v8": "^4.1.8",
     "eslint": "^10.2.0",
     "eslint-config-prettier": "^10.1.8",
     "husky": "^9.1.7",
     "prettier": "^3.8.2",
-    "typescript-eslint": "^8.58.2"
+    "typescript-eslint": "^8.58.2",
+    "vitest": "^4.1.8"
   },
   "overrides": {
     "vite": "^6.4.2",
-    "esbuild": "^0.25.0"
+    "esbuild": "^0.25.0",
+    "vitest": "^4.1.8",
+    "@vitest/coverage-v8": "^4.1.8"
   }
 }
diff --git a/packages/bridge-plugin/package.json b/packages/bridge-plugin/package.json
index 464d676..5f29f89 100644
--- a/packages/bridge-plugin/package.json
+++ b/packages/bridge-plugin/package.json
@@ -16,7 +16,7 @@
     "html-webpack-plugin": "^5.6.0",
     "ts-loader": "^9.5.0",
     "typescript": "^5.5.0",
-    "vitest": "^2.1.0",
+    "vitest": "^4.1.8",
     "webpack": "^5.90.0",
     "webpack-cli": "^5.1.0"
   }
diff --git a/packages/bridge-plugin/src/__tests__/discovery.test.ts b/packages/bridge-plugin/src/__tests__/discovery.test.ts
new file mode 100644
index 0000000..52273cb
--- /dev/null
+++ b/packages/bridge-plugin/src/__tests__/discovery.test.ts
@@ -0,0 +1,136 @@
+import { describe, it, expect, beforeEach, afterEach, vi } from "vitest";
+import {
+  fetchStateJson,
+  rankCandidates,
+  discoverCandidatePorts,
+  type StateFile,
+  SUPPORTED_VERSION,
+} from "../discovery.js";
+
+describe("fetchStateJson", () => {
+  beforeEach(() => {
+    vi.stubGlobal("fetch", vi.fn());
+  });
+  afterEach(() => {
+    vi.unstubAllGlobals();
+  });
+
+  it("returns parsed state on 200 with a supported version", async () => {
+    const state: StateFile = {
+      version: 1,
+      pid: 1234,
+      port: 9500,
+      serverVersion: "0.4.3",
+      startedAt: 100,
+      parentPid: 99,
+      parentAlive: true,
+      socketPath: null,
+    };
+    (fetch as unknown as ReturnType<typeof vi.fn>).mockResolvedValueOnce({
+      ok: true,
+      json: async () => state,
+    });
+    const result = await fetchStateJson(9500);
+    expect(result).toEqual(state);
+  });
+
+  it("returns null on a non-200 response", async () => {
+    (fetch as unknown as ReturnType<typeof vi.fn>).mockResolvedValueOnce({ ok: false });
+    expect(await fetchStateJson(9500)).toBeNull();
+  });
+
+  it("returns null when fetch throws", async () => {
+    (fetch as unknown as ReturnType<typeof vi.fn>).mockRejectedValueOnce(new Error("boom"));
+    expect(await fetchStateJson(9500)).toBeNull();
+  });
+
+  it("returns null for a future version", async () => {
+    (fetch as unknown as ReturnType<typeof vi.fn>).mockResolvedValueOnce({
+      ok: true,
+      json: async () => ({ version: SUPPORTED_VERSION + 1, pid: 1, port: 9500 }),
+    });
+    expect(await fetchStateJson(9500)).toBeNull();
+  });
+});
+
+describe("rankCandidates", () => {
+  function makeState(overrides: Partial<StateFile>): StateFile {
+    return {
+      version: 1,
+      pid: 1,
+      port: 9500,
+      serverVersion: "0.4.3",
+      startedAt: 0,
+      parentPid: 99,
+      parentAlive: true,
+      socketPath: null,
+      ...overrides,
+    };
+  }
+
+  it("filters out candidates with parentAlive=false", () => {
+    const ranked = rankCandidates([
+      { port: 9500, state: makeState({ parentAlive: false, startedAt: 100 }) },
+      { port: 9501, state: makeState({ parentAlive: true, startedAt: 50 }) },
+    ]);
+    expect(ranked).toHaveLength(1);
+    expect(ranked[0].port).toBe(9501);
+  });
+
+  it("sorts by startedAt descending (newest first)", () => {
+    const ranked = rankCandidates([
+      { port: 9500, state: makeState({ startedAt: 100 }) },
+      { port: 9501, state: makeState({ startedAt: 200 }) },
+      { port: 9502, state: makeState({ startedAt: 150 }) },
+    ]);
+    expect(ranked.map((c) => c.port)).toEqual([9501, 9502, 9500]);
+  });
+});
+
+describe("discoverCandidatePorts (probe-and-rank end-to-end)", () => {
+  beforeEach(() => {
+    vi.stubGlobal("fetch", vi.fn());
+  });
+  afterEach(() => {
+    vi.unstubAllGlobals();
+  });
+
+  it("returns ranked candidates, excluding orphans", async () => {
+    const orphan: StateFile = {
+      version: 1,
+      pid: 1,
+      port: 9500,
+      serverVersion: "0.4.3",
+      startedAt: 100,
+      parentPid: 99,
+      parentAlive: false,
+      socketPath: null,
+    };
+    const live: StateFile = {
+      version: 1,
+      pid: 2,
+      port: 9501,
+      serverVersion: "0.4.3",
+      startedAt: 200,
+      parentPid: 100,
+      parentAlive: true,
+      socketPath: null,
+    };
+    const fetchMock = fetch as unknown as ReturnType<typeof vi.fn>;
+    fetchMock.mockImplementation(async (url: string) => {
+      if (url.includes(":9500")) return { ok: true, json: async () => orphan };
+      if (url.includes(":9501")) return { ok: true, json: async () => live };
+      throw new Error("ECONNREFUSED");
+    });
+    const ranked = await discoverCandidatePorts([9500, 9501, 9502]);
+    expect(ranked).toHaveLength(1);
+    expect(ranked[0].port).toBe(9501);
+  });
+
+  it("returns empty when no servers respond", async () => {
+    const fetchMock = fetch as unknown as ReturnType<typeof vi.fn>;
+    fetchMock.mockRejectedValue(new Error("ECONNREFUSED"));
+    const ranked = await discoverCandidatePorts([9500, 9501]);
+    expect(ranked).toEqual([]);
+  });
+});
diff --git a/packages/bridge-plugin/src/discovery.ts b/packages/bridge-plugin/src/discovery.ts
new file mode 100644
index 0000000..2a69a0a
--- /dev/null
+++ b/packages/bridge-plugin/src/discovery.ts
@@ -0,0 +1,63 @@
+export interface StateFile {
+  version: 1;
+  pid: number;
+  port: number;
+  serverVersion: string;
+  startedAt: number;
+  parentPid: number;
+  parentAlive: boolean;
+  socketPath: string | null;
+}
+
+export const SUPPORTED_VERSION = 1;
+export const FETCH_TIMEOUT_MS = 300;
+
+export interface DiscoveryCandidate {
+  port: number;
+  state: StateFile;
+}
+
+export async function fetchStateJson(port: number): Promise<StateFile | null> {
+  try {
+    const controller = new AbortController();
+    const t = setTimeout(() => controller.abort(), FETCH_TIMEOUT_MS);
+    let res: Response;
+    try {
+      res = await fetch(`http://127.0.0.1:${port}/state.json`, {
+        signal: controller.signal,
+      });
+      if (!res.ok) return null;
+      const body = (await res.json()) as unknown;
+      if (
+        typeof body === "object" &&
+        body !== null &&
+        typeof (body as { version?: unknown }).version === "number" &&
+        (body as { version: number }).version <= SUPPORTED_VERSION
+      ) {
+        return body as StateFile;
+      }
+      return null;
+    } finally {
+      clearTimeout(t);
+    }
+  } catch {
+    return null;
+  }
+}
+
+export function rankCandidates(candidates: DiscoveryCandidate[]): DiscoveryCandidate[] {
+  return candidates
+    .filter((c) => c.state.parentAlive !== false)
+    .sort((a, b) => b.state.startedAt - a.state.startedAt);
+}
+
+export async function discoverCandidatePorts(ports: number[]): Promise<DiscoveryCandidate[]> {
+  const probed = await Promise.all(
+    ports.map(async (port) => {
+      const state = await fetchStateJson(port);
+      return state ? { port, state } : null;
+    })
+  );
+  const candidates = probed.filter((c): c is DiscoveryCandidate => c !== null);
+  return rankCandidates(candidates);
+}
diff --git a/packages/bridge-plugin/src/ui-entry.ts b/packages/bridge-plugin/src/ui-entry.ts
index db5e8a4..63e1258 100644
--- a/packages/bridge-plugin/src/ui-entry.ts
+++ b/packages/bridge-plugin/src/ui-entry.ts
@@ -3,6 +3,7 @@ import { attachThemeListener, detectInitialTheme, applyTheme } from "./ui/theme"
 import { getLastPort, setLastPort } from "./ui/storage";
 import { ActivityLog, type LogEntry } from "./ui/activity-log";
 import { isCompatible } from "./ui/version-check";
+import { discoverCandidatePorts } from "./discovery";
 import {
   VERSION,
   DXT_DOWNLOAD_URL,
@@ -171,13 +172,29 @@ async function scanAndConnect(): Promise<void> {
     if (lastPort) order.push(lastPort);
     for (let p = PORT_MIN; p <= PORT_MAX; p++) if (p !== lastPort) order.push(p);
 
+    // Phase 1: discovery probe — find live servers via /state.json
+    const ranked = await discoverCandidatePorts(order);
+
+    // Phase 2: try ranked candidates first (parentAlive=true, newest first)
+    for (const candidate of ranked) {
+      const ok = await tryConnect(candidate.port);
+      if (ok) {
+        setLastPort(candidate.port);
+        return;
+      }
+    }
+
+    // Phase 3: fallback — try all ports in original order (preserves existing scan behavior)
+    const triedPorts = new Set(ranked.map((c) => c.port));
     for (const port of order) {
+      if (triedPorts.has(port)) continue;
       const ok = await tryConnect(port);
       if (ok) {
         setLastPort(port);
         return;
       }
     }
+
     setStatus("disconnected");
     scheduleReconnect();
   } finally {
diff --git a/packages/claude-plugin/package.json b/packages/claude-plugin/package.json
index eba7463..649e9f6 100644
--- a/packages/claude-plugin/package.json
+++ b/packages/claude-plugin/package.json
@@ -10,7 +10,7 @@
   },
   "devDependencies": {
     "tsx": "^4.0.0",
-    "vitest": "^1.0.0",
-    "typescript": "^5.0.0"
+    "typescript": "^5.0.0",
+    "vitest": "^4.1.8"
   }
 }
diff --git a/packages/claude-plugin/skills/pluginos-figma/SKILL.md b/packages/claude-plugin/skills/pluginos-figma/SKILL.md
index 9df2c55..a43d03b 100644
--- a/packages/claude-plugin/skills/pluginos-figma/SKILL.md
+++ b/packages/claude-plugin/skills/pluginos-figma/SKILL.md
@@ -59,6 +59,7 @@ If any `pluginos.*` tool returns "No plugin connected" or times out:
 1. Tell the user: "Open the PluginOS Bridge plugin in Figma (Plugins → PluginOS Bridge → Run), then let me know."
 2. Do NOT silently fall back to Figma MCP.
 3. Wait for confirmation before retrying.
+4. If the user relaunches the plugin mid-task, call `pluginos.wait_for_reconnect({ timeoutSec: 60 })` to gracefully block until reconnect, then retry the failed op.
 
 ## Don'ts
 
diff --git a/packages/mcp-server/package.json b/packages/mcp-server/package.json
index 698f9d7..ef4241f 100644
--- a/packages/mcp-server/package.json
+++ b/packages/mcp-server/package.json
@@ -53,11 +53,11 @@
     "@pluginos/shared": "*",
     "@types/adm-zip": "^0.5.8",
     "@types/ws": "^8.5.0",
-    "@vitest/coverage-v8": "^2.1.9",
+    "@vitest/coverage-v8": "^4.1.8",
     "adm-zip": "^0.5.17",
     "tsup": "^8.5.1",
     "tsx": "^4.19.0",
     "typescript": "^5.5.0",
-    "vitest": "^2.1.0"
+    "vitest": "^4.1.8"
   }
 }
diff --git a/packages/mcp-server/src/__tests__/http-state-endpoint.test.ts b/packages/mcp-server/src/__tests__/http-state-endpoint.test.ts
new file mode 100644
index 0000000..14c407c
--- /dev/null
+++ b/packages/mcp-server/src/__tests__/http-state-endpoint.test.ts
@@ -0,0 +1,47 @@
+import { describe, it, expect } from "vitest";
+import { createHttpServer } from "../http-server.js";
+import type { StateFile } from "../singleton/types.js";
+
+describe("HTTP /state.json endpoint", () => {
+  it("returns the current state object when set", async () => {
+    const state: StateFile = {
+      version: 1,
+      pid: 1234,
+      port: 9500,
+      serverVersion: "0.4.3",
+      startedAt: 1700000000000,
+      parentPid: 99,
+      parentAlive: true,
+      socketPath: null,
+    };
+    const server = createHttpServer(
+      () => "<html></html>",
+      () => state
+    );
+    await new Promise<void>((r) => server.listen(0, "127.0.0.1", () => r()));
+    const port = (server.address() as { port: number }).port;
+    try {
+      const res = await fetch(`http://127.0.0.1:${port}/state.json`);
+      expect(res.status).toBe(200);
+      const body = await res.json();
+      expect(body).toEqual(state);
+    } finally {
+      server.close();
+    }
+  });
+
+  it("returns 503 when no state is set", async () => {
+    const server = createHttpServer(
+      () => "<html></html>",
+      () => null
+    );
+    await new Promise<void>((r) => server.listen(0, "127.0.0.1", () => r()));
+    const port = (server.address() as { port: number }).port;
+    try {
+      const res = await fetch(`http://127.0.0.1:${port}/state.json`);
+      expect(res.status).toBe(503);
+    } finally {
+      server.close();
+    }
+  });
+});
diff --git a/packages/mcp-server/src/__tests__/wait-for-reconnect.test.ts b/packages/mcp-server/src/__tests__/wait-for-reconnect.test.ts
new file mode 100644
index 0000000..3feff43
--- /dev/null
+++ b/packages/mcp-server/src/__tests__/wait-for-reconnect.test.ts
@@ -0,0 +1,78 @@
+import { describe, it, expect, vi } from "vitest";
+import type { IPluginBridge } from "@pluginos/shared";
+import { createPluginOSServer } from "../server.js";
+import { Client } from "@modelcontextprotocol/sdk/client/index.js";
+import { InMemoryTransport } from "@modelcontextprotocol/sdk/inMemory.js";
+
+type ToolResult = { content: Array<{ type: string; text: string }>; isError?: boolean };
+
+function makeBridge(isConnected: () => boolean): IPluginBridge {
+  return {
+    sendAndWait: vi.fn(),
+    getStatus: vi.fn().mockReturnValue({
+      connected: isConnected(),
+      fileKey: "mock-file",
+      fileName: "Mock File",
+      currentPage: "Page 1",
+      port: 9500,
+      connectedFiles: 1,
+    }),
+    listFiles: vi.fn().mockReturnValue([]),
+    isConnected: vi.fn(isConnected),
+  } as unknown as IPluginBridge;
+}
+
+async function setupClient(bridge: IPluginBridge) {
+  const server = createPluginOSServer(bridge);
+  const [c, s] = InMemoryTransport.createLinkedPair();
+  await server.connect(s);
+  const client = new Client({ name: "t", version: "1" });
+  await client.connect(c);
+  return client;
+}
+
+describe("wait_for_reconnect tool", () => {
+  it("returns connected immediately when bridge is already connected", async () => {
+    const bridge = makeBridge(() => true);
+    const client = await setupClient(bridge);
+    const res = (await client.callTool({
+      name: "wait_for_reconnect",
+      arguments: { timeoutSec: 5 },
+    })) as ToolResult;
+    expect(res.isError).toBeFalsy();
+    const payload = JSON.parse(res.content[0].text);
+    expect(payload.connected).toBe(true);
+    expect(payload.waitedMs).toBeLessThan(700);
+  });
+
+  it("returns timeout response when bridge never connects", async () => {
+    const bridge = makeBridge(() => false);
+    const client = await setupClient(bridge);
+    const res = (await client.callTool({
+      name: "wait_for_reconnect",
+      arguments: { timeoutSec: 2 },
+    })) as ToolResult;
+    expect(res.isError).toBe(true);
+    const payload = JSON.parse(res.content[0].text);
+    expect(payload.connected).toBe(false);
+    expect(payload.waitedMs).toBeGreaterThanOrEqual(2000);
+  }, 5000);
+
+  it("returns connected when bridge connects mid-wait", async () => {
+    let connected = false;
+    const bridge = makeBridge(() => connected);
+    const client = await setupClient(bridge);
+    setTimeout(() => {
+      connected = true;
+    }, 500);
+    const res = (await client.callTool({
+      name: "wait_for_reconnect",
+      arguments: { timeoutSec: 5 },
+    })) as ToolResult;
+    expect(res.isError).toBeFalsy();
+    const payload = JSON.parse(res.content[0].text);
+    expect(payload.connected).toBe(true);
+    expect(payload.waitedMs).toBeGreaterThanOrEqual(500);
+    expect(payload.waitedMs).toBeLessThan(1500);
+  });
+});
diff --git a/packages/mcp-server/src/http-server.ts b/packages/mcp-server/src/http-server.ts
index 76c2486..68e8130 100644
--- a/packages/mcp-server/src/http-server.ts
+++ b/packages/mcp-server/src/http-server.ts
@@ -1,6 +1,10 @@
 import { createServer, IncomingMessage, ServerResponse, Server } from "http";
+import type { StateFile } from "./singleton/types.js";
 
-export function createHttpServer(getUiContent: () => string): Server {
+export function createHttpServer(
+  getUiContent: () => string,
+  getStateFile?: () => StateFile | null
+): Server {
   const server = createServer((req: IncomingMessage, res: ServerResponse) => {
     // CORS for Figma plugin iframe
     res.setHeader("Access-Control-Allow-Origin", "*");
@@ -13,6 +17,23 @@ export function createHttpServer(getUiContent: () => string): Server {
       return;
     }
 
+    if (req.url === "/state.json" && req.method === "GET") {
+      if (!getStateFile) {
+        res.writeHead(503, { "Content-Type": "text/plain" });
+        res.end("No state available");
+        return;
+      }
+      const state = getStateFile();
+      if (state === null) {
+        res.writeHead(503, { "Content-Type": "text/plain" });
+        res.end("No state available");
+        return;
+      }
+      res.writeHead(200, { "Content-Type": "application/json" });
+      res.end(JSON.stringify(state));
+      return;
+    }
+
     if (req.url === "/ui" || req.url === "/ui.html") {
       res.writeHead(200, {
         "Content-Type": "text/html; charset=utf-8",
diff --git a/packages/mcp-server/src/index.ts b/packages/mcp-server/src/index.ts
index 742eeed..d02c75a 100644
--- a/packages/mcp-server/src/index.ts
+++ b/packages/mcp-server/src/index.ts
@@ -5,6 +5,15 @@ import { createHttpServer } from "./http-server.js";
 import { readFileSync, existsSync } from "fs";
 import { join, dirname } from "path";
 import { fileURLToPath } from "url";
+import {
+  acquireSingletonLock,
+  writeSingletonState,
+  clearSingletonState,
+  buildStateFile,
+  writeStateFile,
+} from "./singleton/index.js";
+import { unlinkSync } from "node:fs";
+import type { SingletonInfo, StateFile } from "./singleton/index.js";
 
 export { createPluginOSServer } from "./server.js";
 export {
@@ -34,16 +43,120 @@ function loadUiContent(): string {
   return "<html><body><p>PluginOS UI not found. Run: npm run build -w packages/bridge-plugin</p></body></html>";
 }
 
-async function main() {
-  // Re-read on every request so rebuilds land without restarting the server.
-  // ui.html is ~70KB; the tradeoff is worth the smoother dev loop and avoids
-  // stale UIs when users swap between local and published builds.
-  const httpServer = createHttpServer(() => loadUiContent());
+// Capture the original parent PID at module load. process.ppid returns 1 (init)
+// on Unix after the actual parent dies due to re-parenting — checking against
+// the captured initial PID detects the orphan condition reliably.
+const INITIAL_PARENT_PID = process.ppid;
+
+let singletonInfo: SingletonInfo | null = null;
+let currentParentAlive = true;
+let parentLivenessInterval: NodeJS.Timeout | null = null;
+let selfTerminateTimeout: NodeJS.Timeout | null = null;
+let currentState: StateFile | null = null;
+
+const PARENT_LIVENESS_INTERVAL_MS = 10_000;
+const ORPHAN_GRACE_MS = 30_000;
+
+function isProcessAlive(pid: number): boolean {
+  try {
+    process.kill(pid, 0);
+    return true;
+  } catch (err) {
+    return (err as NodeJS.ErrnoException).code === "EPERM";
+  }
+}
+
+function registerShutdownHandlers(): void {
+  const cleanup = async (): Promise<void> => {
+    if (singletonInfo) {
+      await clearSingletonState(singletonInfo);
+    }
+    if (parentLivenessInterval) {
+      clearInterval(parentLivenessInterval);
+      parentLivenessInterval = null;
+    }
+    if (selfTerminateTimeout) {
+      clearTimeout(selfTerminateTimeout);
+      selfTerminateTimeout = null;
+    }
+  };
+  process.on("SIGTERM", async () => {
+    await cleanup();
+    process.exit(0);
+  });
+  process.on("SIGINT", async () => {
+    await cleanup();
+    process.exit(0);
+  });
+  process.on("exit", () => {
+    if (singletonInfo) {
+      try {
+        unlinkSync(singletonInfo.stateFilePath);
+      } catch {
+        // ignored
+      }
+      try {
+        unlinkSync(singletonInfo.pidFilePath);
+      } catch {
+        // ignored
+      }
+    }
+  });
+}
+
+async function startParentLivenessHeartbeat(initialState: StateFile): Promise<void> {
+  parentLivenessInterval = setInterval(async () => {
+    if (!singletonInfo) return;
+    const alive = isProcessAlive(INITIAL_PARENT_PID);
+    if (alive !== currentParentAlive) {
+      currentParentAlive = alive;
+      const updated: StateFile = { ...initialState, parentAlive: alive };
+      currentState = updated;
+      await writeStateFile(singletonInfo.stateFilePath, updated);
+    }
+    if (!alive && selfTerminateTimeout === null) {
+      console.error(
+        `[singleton] Parent PID ${initialState.parentPid} is dead. Self-terminating in ${ORPHAN_GRACE_MS / 1000}s.`
+      );
+      selfTerminateTimeout = setTimeout(() => {
+        console.error("[singleton] Grace period elapsed. Exiting.");
+        process.exit(0);
+      }, ORPHAN_GRACE_MS);
+    }
+  }, PARENT_LIVENESS_INTERVAL_MS);
+}
+
+async function main(): Promise<void> {
+  singletonInfo = await acquireSingletonLock();
+  if (singletonInfo.takeoverFromPid !== undefined) {
+    console.error(`PluginOS server: took over from PID ${singletonInfo.takeoverFromPid}`);
+  }
+  registerShutdownHandlers();
+
+  const httpServer = createHttpServer(
+    () => loadUiContent(),
+    () => currentState
+  );
 
   const wsServer = new WebSocketPluginBridge({ httpServer });
   const port = await wsServer.start();
   console.error(`PluginOS WebSocket + HTTP server on port ${port}`);
 
+  // Read package version for state.json
+  const pkgPath = join(__dirname, "..", "package.json");
+  const pkg = JSON.parse(readFileSync(pkgPath, "utf-8")) as { version: string };
+
+  const state = buildStateFile({
+    pid: process.pid,
+    port,
+    serverVersion: pkg.version,
+    parentPid: INITIAL_PARENT_PID,
+    parentAlive: true,
+  });
+  currentState = state;
+  await writeSingletonState(singletonInfo, state);
+  await startParentLivenessHeartbeat(state);
+
   const mcpServer = createPluginOSServer(wsServer);
   const transport = new StdioServerTransport();
   await mcpServer.connect(transport);
diff --git a/packages/mcp-server/src/server.ts b/packages/mcp-server/src/server.ts
index 8e8e4be..8d91106 100644
--- a/packages/mcp-server/src/server.ts
+++ b/packages/mcp-server/src/server.ts
@@ -206,5 +206,69 @@ export function createPluginOSServer(bridge: IPluginBridge) {
     }
   );
 
+  server.tool(
+    "wait_for_reconnect",
+    "Wait for the PluginOS Bridge plugin to reconnect after a disconnect. " +
+      "Returns when the bridge reports connected, or when timeoutSec elapses. " +
+      "Use this when a prior tool call returned 'No plugin connected' to gracefully " +
+      "wait for the user to relaunch the plugin instead of immediately failing back to chat.",
+    {
+      timeoutSec: z
+        .number()
+        .int()
+        .min(1)
+        .max(300)
+        .default(60)
+        .describe("Maximum seconds to wait. Default 60, max 300."),
+    },
+    async ({ timeoutSec }) => {
+      const startedAt = Date.now();
+      const startedHrTime = process.hrtime.bigint();
+      const timeoutNs = BigInt(timeoutSec) * 1_000_000_000n;
+
+      while (process.hrtime.bigint() - startedHrTime < timeoutNs) {
+        if (bridge.isConnected()) {
+          const status = bridge.getStatus();
+          return {
+            content: [
+              {
+                type: "text" as const,
+                text: JSON.stringify(
+                  {
+                    connected: true,
+                    waitedMs: Date.now() - startedAt,
+                    fileName: status.fileName,
+                    fileKey: status.fileKey,
+                  },
+                  null,
+                  2
+                ),
+              },
+            ],
+          };
+        }
+        await new Promise((r) => setTimeout(r, 500));
+      }
+
+      return {
+        content: [
+          {
+            type: "text" as const,
+            text: JSON.stringify(
+              {
+                connected: false,
+                waitedMs: Date.now() - startedAt,
+                timeoutSec,
+              },
+              null,
+              2
+            ),
+          },
+        ],
+        isError: true,
+      };
+    }
+  );
+
   return server;
 }
diff --git a/packages/mcp-server/src/singleton/__tests__/fixtures/mock-server.ts b/packages/mcp-server/src/singleton/__tests__/fixtures/mock-server.ts
new file mode 100644
index 0000000..21a0cd5
--- /dev/null
+++ b/packages/mcp-server/src/singleton/__tests__/fixtures/mock-server.ts
@@ -0,0 +1,45 @@
+import {
+  acquireSingletonLock,
+  writeSingletonState,
+  buildStateFile,
+  clearSingletonState,
+} from "../../index.js";
+
+const stateDir = process.env.PLUGINOS_STATE_DIR;
+if (!stateDir) {
+  console.error("PLUGINOS_STATE_DIR not set");
+  process.exit(2);
+}
+
+async function main(): Promise<void> {
+  const info = await acquireSingletonLock({ stateDir });
+  const state = buildStateFile({
+    pid: process.pid,
+    port: 9500,
+    serverVersion: "test",
+    parentPid: process.ppid,
+    parentAlive: true,
+  });
+  await writeSingletonState(info, state);
+
+  if (process.send) {
+    process.send({ ready: true, takeoverFromPid: info.takeoverFromPid });
+  }
+
+  await new Promise<void>((resolve) => {
+    // keepalive timer — without an active handle Node exits immediately
+    const keepalive = setInterval(() => {}, 60_000);
+
+    process.on("SIGTERM", async () => {
+      clearInterval(keepalive);
+      await clearSingletonState(info);
+      resolve();
+      process.exit(0);
+    });
+  });
+}
+
+main().catch((err) => {
+  console.error("mock-server fatal:", err);
+  process.exit(1);
+});
diff --git a/packages/mcp-server/src/singleton/__tests__/integration.test.ts b/packages/mcp-server/src/singleton/__tests__/integration.test.ts
new file mode 100644
index 0000000..ad26e4e
--- /dev/null
+++ b/packages/mcp-server/src/singleton/__tests__/integration.test.ts
@@ -0,0 +1,91 @@
+import { describe, it, expect, beforeEach, afterEach } from "vitest";
+import { fork, ChildProcess } from "node:child_process";
+import { mkdtemp, rm, readFile } from "node:fs/promises";
+import { tmpdir } from "node:os";
+import { join, dirname } from "node:path";
+import { fileURLToPath } from "node:url";
+
+const __dirname = dirname(fileURLToPath(import.meta.url));
+const fixturePath = join(__dirname, "fixtures", "mock-server.ts");
+
+interface ReadyMessage {
+  ready: boolean;
+  takeoverFromPid?: number;
+}
+
+function spawnMockServer(stateDir: string): Promise<{
+  proc: ChildProcess;
+  ready: ReadyMessage;
+}> {
+  return new Promise((resolve, reject) => {
+    const proc = fork(fixturePath, {
+      env: { ...process.env, PLUGINOS_STATE_DIR: stateDir },
+      execArgv: ["--import", "tsx"],
+      stdio: ["ignore", "pipe", "pipe", "ipc"],
+    });
+    proc.once("error", reject);
+    proc.once("message", (msg) => resolve({ proc, ready: msg as ReadyMessage }));
+  });
+}
+
+function waitForExit(proc: ChildProcess, timeoutMs: number): Promise<number | null> {
+  // If the process already exited, return immediately.
+  if (proc.exitCode !== null || proc.signalCode !== null) {
+    return Promise.resolve(proc.exitCode);
+  }
+  return new Promise((resolve) => {
+    let resolved = false;
+    proc.once("exit", (code) => {
+      if (!resolved) {
+        resolved = true;
+        resolve(code);
+      }
+    });
+    setTimeout(() => {
+      if (!resolved) {
+        resolved = true;
+        resolve(null);
+      }
+    }, timeoutMs);
+  });
+}
+
+describe("singleton integration: two-process takeover", () => {
+  let dir: string;
+
+  beforeEach(async () => {
+    dir = await mkdtemp(join(tmpdir(), "pluginos-integ-test-"));
+  });
+
+  afterEach(async () => {
+    await rm(dir, { recursive: true, force: true });
+  });
+
+  it("second invocation reaps the first and reports takeoverFromPid", async () => {
+    const first = await spawnMockServer(dir);
+    expect(first.ready.ready).toBe(true);
+    expect(first.ready.takeoverFromPid).toBeUndefined();
+
+    const firstPid = first.proc.pid!;
+
+    const second = await spawnMockServer(dir);
+    expect(second.ready.ready).toBe(true);
+    expect(second.ready.takeoverFromPid).toBe(firstPid);
+
+    const firstExitCode = await waitForExit(first.proc, 3000);
+    expect(firstExitCode).not.toBeNull();
+
+    const pidContent = (await readFile(join(dir, "server.pid"), "utf8")).trim();
+    expect(Number.parseInt(pidContent, 10)).toBe(second.proc.pid);
+
+    second.proc.kill("SIGTERM");
+    await waitForExit(second.proc, 3000);
+  }, 15000);
+
+  it("a fresh start with no prior state has no takeoverFromPid", async () => {
+    const one = await spawnMockServer(dir);
+    expect(one.ready.takeoverFromPid).toBeUndefined();
+    one.proc.kill("SIGTERM");
+    await waitForExit(one.proc, 3000);
+  }, 10000);
+});
diff --git a/packages/mcp-server/src/singleton/__tests__/lockfile.test.ts b/packages/mcp-server/src/singleton/__tests__/lockfile.test.ts
new file mode 100644
index 0000000..7b660d7
--- /dev/null
+++ b/packages/mcp-server/src/singleton/__tests__/lockfile.test.ts
@@ -0,0 +1,49 @@
+import { describe, it, expect, beforeEach, afterEach } from "vitest";
+import { mkdtemp, rm } from "node:fs/promises";
+import { tmpdir } from "node:os";
+import { join } from "node:path";
+import { acquireLock, releaseLock } from "../lockfile.js";
+
+describe("lockfile primitive", () => {
+  let dir: string;
+
+  beforeEach(async () => {
+    dir = await mkdtemp(join(tmpdir(), "pluginos-lock-test-"));
+  });
+
+  afterEach(async () => {
+    await rm(dir, { recursive: true, force: true });
+  });
+
+  it("acquires a lock on a fresh path", async () => {
+    const lockPath = join(dir, "server.pid.lock");
+    const result = await acquireLock(lockPath);
+    expect(result.acquired).toBe(true);
+    expect(result.oldPid).toBeNull();
+  });
+
+  it("fails to acquire when held by a live PID", async () => {
+    const lockPath = join(dir, "server.pid.lock");
+    await acquireLock(lockPath);
+    const result = await acquireLock(lockPath, { maxRetries: 1, retryDelayMs: 10 });
+    expect(result.acquired).toBe(false);
+    expect(result.oldPid).toBe(process.pid);
+  });
+
+  it("releases the lock", async () => {
+    const lockPath = join(dir, "server.pid.lock");
+    await acquireLock(lockPath);
+    await releaseLock(lockPath);
+    const result = await acquireLock(lockPath);
+    expect(result.acquired).toBe(true);
+  });
+
+  it("treats a lockfile with a dead PID as stale and takes over", async () => {
+    const lockPath = join(dir, "server.pid.lock");
+    const { writeFileSync } = await import("node:fs");
+    writeFileSync(lockPath, "999999999");
+    const result = await acquireLock(lockPath, { maxRetries: 1, retryDelayMs: 10 });
+    expect(result.acquired).toBe(true);
+    expect(result.oldPid).toBe(999999999);
+  });
+});
diff --git a/packages/mcp-server/src/singleton/__tests__/orchestrator.test.ts b/packages/mcp-server/src/singleton/__tests__/orchestrator.test.ts
new file mode 100644
index 0000000..f381dfc
--- /dev/null
+++ b/packages/mcp-server/src/singleton/__tests__/orchestrator.test.ts
@@ -0,0 +1,44 @@
+import { describe, it, expect, beforeEach, afterEach } from "vitest";
+import { mkdtemp, rm, writeFile } from "node:fs/promises";
+import { tmpdir } from "node:os";
+import { join } from "node:path";
+import { acquireSingletonLock } from "../index.js";
+
+describe("acquireSingletonLock", () => {
+  let stateDir: string;
+
+  beforeEach(async () => {
+    stateDir = await mkdtemp(join(tmpdir(), "pluginos-orch-test-"));
+  });
+
+  afterEach(async () => {
+    await rm(stateDir, { recursive: true, force: true });
+  });
+
+  it("acquires on a fresh dir with no prior server", async () => {
+    const info = await acquireSingletonLock({ stateDir });
+    expect(info.takeoverFromPid).toBeUndefined();
+    expect(info.stateDir).toBe(stateDir);
+    expect(info.pidFilePath).toBe(join(stateDir, "server.pid"));
+    expect(info.stateFilePath).toBe(join(stateDir, "state.json"));
+    expect(info.lockFilePath).toBe(join(stateDir, "server.pid.lock"));
+  });
+
+  it("reaps a stale PID and reports takeoverFromPid", async () => {
+    await writeFile(join(stateDir, "server.pid"), "999999998");
+    const info = await acquireSingletonLock({ stateDir });
+    expect(info.takeoverFromPid).toBe(999999998);
+  });
+
+  it("creates the state dir if missing", async () => {
+    const missingDir = join(stateDir, "nested", "pluginos");
+    const info = await acquireSingletonLock({ stateDir: missingDir });
+    expect(info.stateDir).toBe(missingDir);
+  });
+
+  it("returns a degraded info object when the state dir is not writable", async () => {
+    const badDir = "/dev/null/not-a-dir";
+    const info = await acquireSingletonLock({ stateDir: badDir });
+    expect(info.stateDir).toBe(badDir);
+  });
+});
diff --git a/packages/mcp-server/src/singleton/__tests__/pid-file.test.ts b/packages/mcp-server/src/singleton/__tests__/pid-file.test.ts
new file mode 100644
index 0000000..65383a8
--- /dev/null
+++ b/packages/mcp-server/src/singleton/__tests__/pid-file.test.ts
@@ -0,0 +1,47 @@
+import { describe, it, expect, beforeEach, afterEach } from "vitest";
+import { mkdtemp, rm, writeFile } from "node:fs/promises";
+import { tmpdir } from "node:os";
+import { join } from "node:path";
+import { writePidFile, readPidFile, removePidFile } from "../pid-file.js";
+
+describe("pid-file r/w", () => {
+  let dir: string;
+
+  beforeEach(async () => {
+    dir = await mkdtemp(join(tmpdir(), "pluginos-pid-test-"));
+  });
+
+  afterEach(async () => {
+    await rm(dir, { recursive: true, force: true });
+  });
+
+  it("writes a pid atomically (tmp + rename)", async () => {
+    const path = join(dir, "server.pid");
+    await writePidFile(path, 12345);
+    const read = await readPidFile(path);
+    expect(read).toBe(12345);
+  });
+
+  it("returns null for a missing file", async () => {
+    const path = join(dir, "missing.pid");
+    expect(await readPidFile(path)).toBeNull();
+  });
+
+  it("returns null for a corrupt file", async () => {
+    const path = join(dir, "corrupt.pid");
+    await writeFile(path, "not-a-number");
+    expect(await readPidFile(path)).toBeNull();
+  });
+
+  it("removes the pid file", async () => {
+    const path = join(dir, "server.pid");
+    await writePidFile(path, 42);
+    await removePidFile(path);
+    expect(await readPidFile(path)).toBeNull();
+  });
+
+  it("remove is a no-op when file is missing", async () => {
+    const path = join(dir, "missing.pid");
+    await expect(removePidFile(path)).resolves.toBeUndefined();
+  });
+});
diff --git a/packages/mcp-server/src/singleton/__tests__/state-file.test.ts b/packages/mcp-server/src/singleton/__tests__/state-file.test.ts
new file mode 100644
index 0000000..6a76582
--- /dev/null
+++ b/packages/mcp-server/src/singleton/__tests__/state-file.test.ts
@@ -0,0 +1,80 @@
+import { describe, it, expect, beforeEach, afterEach } from "vitest";
+import { mkdtemp, rm, writeFile } from "node:fs/promises";
+import { tmpdir } from "node:os";
+import { join } from "node:path";
+import { buildStateFile, writeStateFile, readStateFile, removeStateFile } from "../state-file.js";
+import type { StateFile } from "../types.js";
+
+describe("state-file", () => {
+  let dir: string;
+
+  beforeEach(async () => {
+    dir = await mkdtemp(join(tmpdir(), "pluginos-state-test-"));
+  });
+
+  afterEach(async () => {
+    await rm(dir, { recursive: true, force: true });
+  });
+
+  it("builds a state object with required fields", () => {
+    const state = buildStateFile({
+      pid: 1234,
+      port: 9500,
+      serverVersion: "0.4.3",
+      parentPid: 99,
+      parentAlive: true,
+    });
+    expect(state.version).toBe(1);
+    expect(state.pid).toBe(1234);
+    expect(state.port).toBe(9500);
+    expect(state.serverVersion).toBe("0.4.3");
+    expect(state.parentPid).toBe(99);
+    expect(state.parentAlive).toBe(true);
+    expect(state.socketPath).toBeNull();
+    expect(typeof state.startedAt).toBe("number");
+  });
+
+  it("writes atomically (tmp + rename) and reads back", async () => {
+    const path = join(dir, "state.json");
+    const state: StateFile = buildStateFile({
+      pid: 1234,
+      port: 9500,
+      serverVersion: "0.4.3",
+      parentPid: 99,
+      parentAlive: true,
+    });
+    await writeStateFile(path, state);
+    const read = await readStateFile(path);
+    expect(read).toEqual(state);
+  });
+
+  it("reads return null for missing files", async () => {
+    expect(await readStateFile(join(dir, "missing.json"))).toBeNull();
+  });
+
+  it("reads return null for malformed files", async () => {
+    const path = join(dir, "malformed.json");
+    await writeFile(path, "not-json");
+    expect(await readStateFile(path)).toBeNull();
+  });
+
+  it("reads return null for state with wrong version", async () => {
+    const path = join(dir, "future.json");
+    await writeFile(path, JSON.stringify({ version: 999, pid: 1, port: 9500 }));
+    expect(await readStateFile(path)).toBeNull();
+  });
+
+  it("removes the file", async () => {
+    const path = join(dir, "state.json");
+    const state = buildStateFile({
+      pid: 1234,
+      port: 9500,
+      serverVersion: "0.4.3",
+      parentPid: 99,
+      parentAlive: true,
+    });
+    await writeStateFile(path, state);
+    await removeStateFile(path);
+    expect(await readStateFile(path)).toBeNull();
+  });
+});
diff --git a/packages/mcp-server/src/singleton/__tests__/takeover.test.ts b/packages/mcp-server/src/singleton/__tests__/takeover.test.ts
new file mode 100644
index 0000000..47e5878
--- /dev/null
+++ b/packages/mcp-server/src/singleton/__tests__/takeover.test.ts
@@ -0,0 +1,57 @@
+import { describe, it, expect, vi } from "vitest";
+import { reapProcess } from "../takeover.js";
+
+describe("reapProcess", () => {
+  it("sends SIGTERM and returns true when process exits within grace", async () => {
+    const calls: Array<[number, NodeJS.Signals | 0]> = [];
+    let alive = true;
+    const kill = vi.fn((pid: number, sig: NodeJS.Signals | 0) => {
+      calls.push([pid, sig]);
+      if (sig === "SIGTERM") {
+        setTimeout(() => {
+          alive = false;
+        }, 50);
+      }
+      if (sig === 0 && !alive) {
+        const e = new Error("ESRCH") as NodeJS.ErrnoException;
+        e.code = "ESRCH";
+        throw e;
+      }
+      return true;
+    });
+    const result = await reapProcess(12345, { kill, graceMs: 500, pollMs: 25 });
+    expect(result.reaped).toBe(true);
+    expect(result.usedSignal).toBe("SIGTERM");
+    expect(calls.some(([, s]) => s === "SIGTERM")).toBe(true);
+    expect(calls.some(([, s]) => s === "SIGKILL")).toBe(false);
+  });
+
+  it("escalates to SIGKILL when SIGTERM doesn't take", async () => {
+    const calls: Array<[number, NodeJS.Signals | 0]> = [];
+    let alive = true;
+    const kill = vi.fn((pid: number, sig: NodeJS.Signals | 0) => {
+      calls.push([pid, sig]);
+      if (sig === "SIGKILL") {
+        // Process dies immediately on SIGKILL
+        alive = false;
+      }
+      if (sig === 0 && !alive) {
+        const e = new Error("ESRCH") as NodeJS.ErrnoException;
+        e.code = "ESRCH";
+        throw e;
+      }
+      return true;
+    });
+    const result = await reapProcess(12345, { kill, graceMs: 100, pollMs: 25 });
+    expect(result.reaped).toBe(true);
+    expect(result.usedSignal).toBe("SIGKILL");
+    expect(calls.some(([, s]) => s === "SIGTERM")).toBe(true);
+    expect(calls.some(([, s]) => s === "SIGKILL")).toBe(true);
+  });
+
+  it("returns reaped=false if the process never dies even after SIGKILL", async () => {
+    const kill = vi.fn(() => true);
+    const result = await reapProcess(12345, { kill, graceMs: 50, pollMs: 25, postKillWaitMs: 50 });
+    expect(result.reaped).toBe(false);
+  });
+});
diff --git a/packages/mcp-server/src/singleton/index.ts b/packages/mcp-server/src/singleton/index.ts
new file mode 100644
index 0000000..24a586a
--- /dev/null
+++ b/packages/mcp-server/src/singleton/index.ts
@@ -0,0 +1,94 @@
+import { mkdir, chmod } from "node:fs/promises";
+import { join } from "node:path";
+import { homedir } from "node:os";
+import { acquireLock, releaseLock } from "./lockfile.js";
+import { readPidFile, writePidFile, removePidFile } from "./pid-file.js";
+import { reapProcess } from "./takeover.js";
+import { writeStateFile, removeStateFile } from "./state-file.js";
+import type { SingletonInfo, StateFile } from "./types.js";
+
+export { buildStateFile, writeStateFile, readStateFile, removeStateFile } from "./state-file.js";
+export { reapProcess } from "./takeover.js";
+export type { StateFile, SingletonInfo } from "./types.js";
+
+export interface AcquireOptions {
+  stateDir?: string;
+}
+
+function defaultStateDir(): string {
+  return process.env.PLUGINOS_STATE_DIR ?? join(homedir(), ".pluginos");
+}
+
+function isProcessAlive(pid: number): boolean {
+  try {
+    process.kill(pid, 0);
+    return true;
+  } catch (err) {
+    return (err as NodeJS.ErrnoException).code === "EPERM";
+  }
+}
+
+export async function acquireSingletonLock(opts: AcquireOptions = {}): Promise<SingletonInfo> {
+  const stateDir = opts.stateDir ?? defaultStateDir();
+  const pidFilePath = join(stateDir, "server.pid");
+  const stateFilePath = join(stateDir, "state.json");
+  const lockFilePath = join(stateDir, "server.pid.lock");
+
+  try {
+    await mkdir(stateDir, { recursive: true });
+    await chmod(stateDir, 0o700).catch(() => {
+      // chmod can fail on Windows or special FS — ignore
+    });
+  } catch (err) {
+    console.error(
+      `[singleton] Failed to create state dir ${stateDir}: ${(err as Error).message}. Continuing in degraded mode.`
+    );
+    return { stateDir, pidFilePath, stateFilePath, lockFilePath };
+  }
+
+  const lock = await acquireLock(lockFilePath);
+  if (!lock.acquired) {
+    console.error(
+      `[singleton] Could not acquire lock at ${lockFilePath} after retries — proceeding without singleton enforcement.`
+    );
+    return { stateDir, pidFilePath, stateFilePath, lockFilePath };
+  }
+
+  let takeoverFromPid: number | undefined;
+  const oldPid = await readPidFile(pidFilePath);
+  if (oldPid === process.pid) {
+    // The PID file already points to us — nothing to reap.
+    await releaseLock(lockFilePath);
+    return { stateDir, pidFilePath, stateFilePath, lockFilePath };
+  }
+  if (oldPid !== null && isProcessAlive(oldPid)) {
+    const result = await reapProcess(oldPid);
+    if (result.reaped) {
+      takeoverFromPid = oldPid;
+      console.error(`[singleton] Reaped PID ${oldPid} (signal: ${result.usedSignal}). Took over.`);
+    } else {
+      console.error(
+        `[singleton] Could not reap PID ${oldPid} — proceeding anyway. Port collision may occur.`
+      );
+    }
+  } else if (oldPid !== null) {
+    takeoverFromPid = oldPid;
+    console.error(`[singleton] Found stale PID file (${oldPid} not alive). Took over.`);
+  }
+
+  await releaseLock(lockFilePath);
+  return { takeoverFromPid, stateDir, pidFilePath, stateFilePath, lockFilePath };
+}
+
+export async function writeSingletonState(info: SingletonInfo, state: StateFile): Promise<void> {
+  try {
+    await writePidFile(info.pidFilePath, state.pid);
+    await writeStateFile(info.stateFilePath, state);
+  } catch (err) {
+    console.error(`[singleton] Failed to write state files: ${(err as Error).message}`);
+  }
+}
+
+export async function clearSingletonState(info: SingletonInfo): Promise<void> {
+  await Promise.allSettled([removeStateFile(info.stateFilePath), removePidFile(info.pidFilePath)]);
+}
diff --git a/packages/mcp-server/src/singleton/lockfile.ts b/packages/mcp-server/src/singleton/lockfile.ts
new file mode 100644
index 0000000..db13ab4
--- /dev/null
+++ b/packages/mcp-server/src/singleton/lockfile.ts
@@ -0,0 +1,75 @@
+import { open, readFile, unlink } from "node:fs/promises";
+import type { LockAcquisition } from "./types.js";
+
+export interface AcquireOptions {
+  maxRetries?: number;
+  retryDelayMs?: number;
+}
+
+function isProcessAlive(pid: number): boolean {
+  try {
+    process.kill(pid, 0);
+    return true;
+  } catch (err) {
+    return (err as NodeJS.ErrnoException).code === "EPERM";
+  }
+}
+
+async function readPidFromLockfile(path: string): Promise<number | null> {
+  try {
+    const content = (await readFile(path, "utf8")).trim();
+    const pid = Number.parseInt(content, 10);
+    return Number.isFinite(pid) ? pid : null;
+  } catch {
+    return null;
+  }
+}
+
+export async function acquireLock(
+  path: string,
+  opts: AcquireOptions = {}
+): Promise<LockAcquisition> {
+  const maxRetries = opts.maxRetries ?? 5;
+  const retryDelayMs = opts.retryDelayMs ?? 200;
+  let stalePid: number | null = null;
+
+  for (let attempt = 0; attempt <= maxRetries; attempt++) {
+    try {
+      const fh = await open(path, "wx");
+      try {
+        await fh.write(String(process.pid));
+      } finally {
+        await fh.close();
+      }
+      return { acquired: true, oldPid: stalePid };
+    } catch (err) {
+      if ((err as NodeJS.ErrnoException).code !== "EEXIST") throw err;
+
+      const oldPid = await readPidFromLockfile(path);
+      if (oldPid !== null && !isProcessAlive(oldPid)) {
+        stalePid = oldPid;
+        try {
+          await unlink(path);
+        } catch {
+          // race with another process — proceed
+        }
+        continue;
+      }
+
+      if (attempt === maxRetries) {
+        return { acquired: false, oldPid };
+      }
+      await new Promise((r) => setTimeout(r, retryDelayMs));
+    }
+  }
+
+  return { acquired: false, oldPid: null };
+}
+
+export async function releaseLock(path: string): Promise<void> {
+  try {
+    await unlink(path);
+  } catch {
+    // best-effort
+  }
+}
diff --git a/packages/mcp-server/src/singleton/pid-file.ts b/packages/mcp-server/src/singleton/pid-file.ts
new file mode 100644
index 0000000..aa1854b
--- /dev/null
+++ b/packages/mcp-server/src/singleton/pid-file.ts
@@ -0,0 +1,25 @@
+import { writeFile, readFile, rename, unlink } from "node:fs/promises";
+
+export async function writePidFile(path: string, pid: number): Promise<void> {
+  const tmp = `${path}.tmp`;
+  await writeFile(tmp, String(pid));
+  await rename(tmp, path);
+}
+
+export async function readPidFile(path: string): Promise<number | null> {
+  try {
+    const content = (await readFile(path, "utf8")).trim();
+    const pid = Number.parseInt(content, 10);
+    return Number.isFinite(pid) ? pid : null;
+  } catch {
+    return null;
+  }
+}
+
+export async function removePidFile(path: string): Promise<void> {
+  try {
+    await unlink(path);
+  } catch (err) {
+    if ((err as NodeJS.ErrnoException).code !== "ENOENT") throw err;
+  }
+}
diff --git a/packages/mcp-server/src/singleton/state-file.ts b/packages/mcp-server/src/singleton/state-file.ts
new file mode 100644
index 0000000..d610462
--- /dev/null
+++ b/packages/mcp-server/src/singleton/state-file.ts
@@ -0,0 +1,54 @@
+import { writeFile, readFile, rename, unlink } from "node:fs/promises";
+import type { StateFile } from "./types.js";
+
+export interface BuildStateInput {
+  pid: number;
+  port: number;
+  serverVersion: string;
+  parentPid: number;
+  parentAlive: boolean;
+}
+
+export function buildStateFile(input: BuildStateInput): StateFile {
+  return {
+    version: 1,
+    pid: input.pid,
+    port: input.port,
+    serverVersion: input.serverVersion,
+    startedAt: Date.now(),
+    parentPid: input.parentPid,
+    parentAlive: input.parentAlive,
+    socketPath: null,
+  };
+}
+
+export async function writeStateFile(path: string, state: StateFile): Promise<void> {
+  const tmp = `${path}.tmp`;
+  await writeFile(tmp, JSON.stringify(state, null, 2));
+  await rename(tmp, path);
+}
+
+export async function readStateFile(path: string): Promise<StateFile | null> {
+  try {
+    const raw = await readFile(path, "utf8");
+    const parsed = JSON.parse(raw) as unknown;
+    if (
+      typeof parsed === "object" &&
+      parsed !== null &&
+      (parsed as { version?: unknown }).version === 1
+    ) {
+      return parsed as StateFile;
+    }
+    return null;
+  } catch {
+    return null;
+  }
+}
+
+export async function removeStateFile(path: string): Promise<void> {
+  try {
+    await unlink(path);
+  } catch (err) {
+    if ((err as NodeJS.ErrnoException).code !== "ENOENT") throw err;
+  }
+}
diff --git a/packages/mcp-server/src/singleton/takeover.ts b/packages/mcp-server/src/singleton/takeover.ts
new file mode 100644
index 0000000..140efe2
--- /dev/null
+++ b/packages/mcp-server/src/singleton/takeover.ts
@@ -0,0 +1,80 @@
+export interface ReapOptions {
+  kill?: (pid: number, signal: NodeJS.Signals | 0) => boolean;
+  graceMs?: number;
+  pollMs?: number;
+  postKillWaitMs?: number;
+}
+
+export interface ReapResult {
+  reaped: boolean;
+  usedSignal: NodeJS.Signals | null;
+}
+
+function defaultKill(pid: number, signal: NodeJS.Signals | 0): boolean {
+  return process.kill(pid, signal as NodeJS.Signals);
+}
+
+function isAlive(pid: number, kill: (pid: number, signal: 0) => boolean): boolean {
+  try {
+    kill(pid, 0);
+    return true;
+  } catch (err) {
+    const code = (err as NodeJS.ErrnoException).code;
+    if (code === "EPERM") return true;
+    if (code === "ESRCH") return false;
+    return false;
+  }
+}
+
+async function pollUntilDead(
+  pid: number,
+  kill: (pid: number, signal: 0) => boolean,
+  timeoutMs: number,
+  pollMs: number
+): Promise<boolean> {
+  const deadline = Date.now() + timeoutMs;
+  while (Date.now() < deadline) {
+    if (!isAlive(pid, kill)) return true;
+    await new Promise((r) => setTimeout(r, pollMs));
+  }
+  return !isAlive(pid, kill);
+}
+
+export async function reapProcess(pid: number, opts: ReapOptions = {}): Promise<ReapResult> {
+  if (pid === process.pid) {
+    return { reaped: false, usedSignal: null };
+  }
+  const kill = opts.kill ?? defaultKill;
+  const graceMs = opts.graceMs ?? 1000;
+  const pollMs = opts.pollMs ?? 100;
+  const postKillWaitMs = opts.postKillWaitMs ?? 200;
+
+  try {
+    kill(pid, "SIGTERM");
+  } catch {
+    // process may already be dead — that's fine
+  }
+
+  const diedFromSigterm = await pollUntilDead(
+    pid,
+    (p, s) => kill(p, s as NodeJS.Signals | 0),
+    graceMs,
+    pollMs
+  );
+  if (diedFromSigterm) {
+    return { reaped: true, usedSignal: "SIGTERM" };
+  }
+
+  try {
+    kill(pid, "SIGKILL");
+  } catch {
+    // proceed
+  }
+  const diedFromSigkill = await pollUntilDead(
+    pid,
+    (p, s) => kill(p, s as NodeJS.Signals | 0),
+    postKillWaitMs,
+    pollMs
+  );
+  return { reaped: diedFromSigkill, usedSignal: diedFromSigkill ? "SIGKILL" : null };
+}
diff --git a/packages/mcp-server/src/singleton/types.ts b/packages/mcp-server/src/singleton/types.ts
new file mode 100644
index 0000000..73d8dac
--- /dev/null
+++ b/packages/mcp-server/src/singleton/types.ts
@@ -0,0 +1,25 @@
+// packages/mcp-server/src/singleton/types.ts
+
+export interface StateFile {
+  version: 1;
+  pid: number;
+  port: number;
+  serverVersion: string;
+  startedAt: number;
+  parentPid: number;
+  parentAlive: boolean;
+  socketPath: string | null;
+}
+
+export interface SingletonInfo {
+  takeoverFromPid?: number;
+  stateDir: string;
+  pidFilePath: string;
+  stateFilePath: string;
+  lockFilePath: string;
+}
+
+export interface LockAcquisition {
+  acquired: boolean;
+  oldPid: number | null;
+}
diff --git a/packages/shared/package.json b/packages/shared/package.json
index cc84225..24117b4 100644
--- a/packages/shared/package.json
+++ b/packages/shared/package.json
@@ -11,8 +11,8 @@
     "test:coverage": "vitest run --coverage"
   },
   "devDependencies": {
-    "@vitest/coverage-v8": "^2.1.9",
+    "@vitest/coverage-v8": "^4.1.8",
     "typescript": "^5.5.0",
-    "vitest": "^2.1.0"
+    "vitest": "^4.1.8"
   }
 }