diff --git a/packages/web/bin/cli.js b/packages/web/bin/cli.js
index bc9bb830..1c5fc7e5 100755
--- a/packages/web/bin/cli.js
+++ b/packages/web/bin/cli.js
@@ -1821,6 +1821,15 @@ async function terminateProcessTree(pid, options = {}) {
     : 3000;
 
   if (process.platform === 'win32') {
+    try {
+      process.kill(pid);
+    } catch {
+    }
+
+    if (await waitForProcessExit(pid, 800)) {
+      return true;
+    }
+
     try {
       spawnSync('taskkill', ['/pid', String(pid), '/t'], {
         stdio: 'ignore',
diff --git a/packages/web/server/lib/opencode/lifecycle.js b/packages/web/server/lib/opencode/lifecycle.js
index 20d784cf..9d85d028 100644
--- a/packages/web/server/lib/opencode/lifecycle.js
+++ b/packages/web/server/lib/opencode/lifecycle.js
@@ -124,6 +124,15 @@ export const createOpenCodeLifecycleRuntime = (deps) => {
     }
 
     if (process.platform === 'win32') {
+      try {
+        child.kill();
+      } catch {
+      }
+
+      if (await waitForChildProcessClose(child, 800)) {
+        return;
+      }
+
       try {
         spawnSync('taskkill', ['/pid', String(pid), '/t'], {
           stdio: 'ignore',
diff --git a/packages/web/server/lib/terminal/runtime.js b/packages/web/server/lib/terminal/runtime.js
index 2d104b69..2bb38170 100644
--- a/packages/web/server/lib/terminal/runtime.js
+++ b/packages/web/server/lib/terminal/runtime.js
@@ -130,7 +130,7 @@ export function createTerminalRuntime({
     let lastError = null;
     for (const shell of shellCandidates) {
       try {
-        const ptyProcess = pty.spawn(shell, [], {
+        const ptyOptions = {
           name: 'xterm-256color',
           cols: cols || 80,
           rows: rows || 24,
@@ -140,7 +140,13 @@ export function createTerminalRuntime({
             TERM: 'xterm-256color',
             COLORTERM: 'truecolor',
           },
-        });
+        };
+
+        if (process.platform === 'win32') {
+          ptyOptions.useConpty = true;
+        }
+
+        const ptyProcess = pty.spawn(shell, [], ptyOptions);
 
         return { ptyProcess, shell };
       } catch (error) {