diff --git a/packages/web/server/lib/opencode/lifecycle.js b/packages/web/server/lib/opencode/lifecycle.js
index 03734316..6131f547 100644
--- a/packages/web/server/lib/opencode/lifecycle.js
+++ b/packages/web/server/lib/opencode/lifecycle.js
@@ -53,8 +53,35 @@ export const createOpenCodeLifecycleRuntime = (deps) => {
     now = Date.now,
   } = deps;
 
+  const killProcessOnPortWin32 = (port) => {
+    try {
+      const result = spawnSync('netstat', ['-ano'], { encoding: 'utf8', timeout: 5000, windowsHide: true });
+      const output = result.stdout || '';
+      const myPid = process.pid;
+      const listeningPidPattern = /^\s*TCP\s+\S*:(\d+)\s+\S+\s+LISTENING\s+(\d+)\s*$/gim;
+      const pids = new Set();
+      let match;
+      while ((match = listeningPidPattern.exec(output)) !== null) {
+        if (Number.parseInt(match[1], 10) !== port) continue;
+        const pid = Number.parseInt(match[2], 10);
+        if (pid && pid !== myPid) pids.add(pid);
+      }
+      for (const pid of pids) {
+        try {
+          spawnSync('taskkill', ['/PID', String(pid), '/F'], { stdio: 'ignore', timeout: 3000, windowsHide: true });
+        } catch {
+        }
+      }
+    } catch {
+    }
+  };
+
   const killProcessOnPort = (port) => {
-    if (!port || process.platform === 'win32') return;
+    if (!port) return;
+    if (process.platform === 'win32') {
+      killProcessOnPortWin32(port);
+      return;
+    }
     try {
       const result = spawnSync('lsof', ['-ti', `:${port}`], { encoding: 'utf8', timeout: 5000, windowsHide: true });
       const output = result.stdout || '';
@@ -698,10 +725,11 @@ export const createOpenCodeLifecycleRuntime = (deps) => {
       }
 
       // The restart may have landed on a NEW port (the old one can remain
-      // occupied by an orphaned process, e.g. Windows killProcessOnPort is a
-      // no-op). Upstream event readers pinned to the old process would keep
-      // the UI silent forever, so rebind them to the current port. Best
-      // effort: a failure here must not fail the restart itself.
+      // occupied if killProcessOnPort/waitForPortRelease didn't free it in
+      // time, on any platform). Upstream event readers pinned to the old
+      // process would keep the UI silent forever, so rebind them to the
+      // current port. Best effort: a failure here must not fail the restart
+      // itself.
       try {
         onOpenCodeRestarted?.();
       } catch (error) {
diff --git a/packages/web/server/lib/opencode/lifecycle.test.js b/packages/web/server/lib/opencode/lifecycle.test.js
index a5a6d39d..84bbf29b 100644
--- a/packages/web/server/lib/opencode/lifecycle.test.js
+++ b/packages/web/server/lib/opencode/lifecycle.test.js
@@ -2,11 +2,12 @@ import { EventEmitter } from 'node:events';
 import { afterEach, describe, expect, it, vi } from 'vitest';
 
 const spawnMock = vi.fn();
+const spawnSyncMock = vi.fn();
 const recordStartupPerformanceMock = vi.fn();
 
 vi.mock('node:child_process', () => ({
   spawn: spawnMock,
-  spawnSync: vi.fn(),
+  spawnSync: spawnSyncMock,
 }));
 vi.mock('./startup-performance.js', () => ({
   recordStartupPerformance: recordStartupPerformanceMock,
@@ -20,6 +21,7 @@ const originalFetch = globalThis.fetch;
 
 afterEach(() => {
   spawnMock.mockReset();
+  spawnSyncMock.mockReset();
   recordStartupPerformanceMock.mockReset();
   globalThis.fetch = originalFetch;
   if (typeof originalOpencodeBinary === 'string') {
@@ -613,3 +615,75 @@ describe('OpenCode lifecycle', () => {
     await server.close();
   });
 });
+
+describe('killProcessOnPort on Windows', () => {
+  const originalPlatform = process.platform;
+
+  afterEach(() => {
+    Object.defineProperty(process, 'platform', { value: originalPlatform });
+  });
+
+  const setPlatform = (platform) => {
+    Object.defineProperty(process, 'platform', { value: platform, configurable: true });
+  };
+
+  const netstatOutput = (port, pid) => [
+    '',
+    'Active Connections',
+    '',
+    '  Proto  Local Address          Foreign Address        State           PID',
+    `  TCP    0.0.0.0:${port}            0.0.0.0:0              LISTENING       ${pid}`,
+    '',
+  ].join('\r\n');
+
+  it('force-kills the process listening on the target port via taskkill', () => {
+    setPlatform('win32');
+    const orphanPid = 54321;
+    spawnSyncMock.mockImplementation((cmd) => {
+      if (cmd === 'netstat') {
+        return { stdout: netstatOutput(45678, orphanPid) };
+      }
+      return { stdout: '' };
+    });
+
+    const runtime = createRuntime();
+    runtime.killProcessOnPort(45678);
+
+    expect(spawnSyncMock).toHaveBeenCalledWith('netstat', ['-ano'], expect.objectContaining({ windowsHide: true }));
+    expect(spawnSyncMock).toHaveBeenCalledWith(
+      'taskkill',
+      ['/PID', String(orphanPid), '/F'],
+      expect.objectContaining({ windowsHide: true })
+    );
+  });
+
+  it('never force-kills its own process id', () => {
+    setPlatform('win32');
+    spawnSyncMock.mockImplementation((cmd) => {
+      if (cmd === 'netstat') {
+        return { stdout: netstatOutput(45678, process.pid) };
+      }
+      return { stdout: '' };
+    });
+
+    const runtime = createRuntime();
+    runtime.killProcessOnPort(45678);
+
+    expect(spawnSyncMock).not.toHaveBeenCalledWith('taskkill', expect.anything(), expect.anything());
+  });
+
+  it('does nothing when no process is listening on the target port', () => {
+    setPlatform('win32');
+    spawnSyncMock.mockImplementation((cmd) => {
+      if (cmd === 'netstat') {
+        return { stdout: netstatOutput(9999, 54321) };
+      }
+      return { stdout: '' };
+    });
+
+    const runtime = createRuntime();
+    runtime.killProcessOnPort(45678);
+
+    expect(spawnSyncMock).not.toHaveBeenCalledWith('taskkill', expect.anything(), expect.anything());
+  });
+});