diff --git a/package-lock.json b/package-lock.json
index 7c5f0d45b..d01d66717 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -16521,6 +16521,15 @@
       "integrity": "sha512-+AqO1Ae+N/4r7Rvchrdm432afjT9hqJRyBN3DQv9At0tPz4hIFSGKbq64fN9dVoCow4oggIIax5/iONx0r9hZw==",
       "dev": true
     },
+    "pstree.remy": {
+      "version": "1.1.0",
+      "resolved": "https://registry.npmjs.org/pstree.remy/-/pstree.remy-1.1.0.tgz",
+      "integrity": "sha512-q5I5vLRMVtdWa8n/3UEzZX7Lfghzrg9eG2IKk2ENLSofKRCXVqMvMUHxCKgXNaqH/8ebhBxrqftHWnyTFweJ5Q==",
+      "dev": true,
+      "requires": {
+        "ps-tree": "^1.1.0"
+      }
+    },
     "public-encrypt": {
       "version": "4.0.2",
       "resolved": "https://registry.npmjs.org/public-encrypt/-/public-encrypt-4.0.2.tgz",
diff --git a/package.json b/package.json
index 25f5b4d1e..f42f937d2 100644
--- a/package.json
+++ b/package.json
@@ -126,6 +126,7 @@
     "postcss-prepend-imports": "^1.0.1",
     "postcss-preset-env": "^5.2.1",
     "prettier": "^1.13.4",
+    "pstree.remy": "^1.1.0",
     "query-string": "^6.1.0",
     "raw-loader": "^0.5.1",
     "react": "^16.4.0",
diff --git a/scripts/watcher/LongRunningExecutor.ts b/scripts/watcher/LongRunningExecutor.ts
index 7019c1fb3..c1c1b4ff8 100644
--- a/scripts/watcher/LongRunningExecutor.ts
+++ b/scripts/watcher/LongRunningExecutor.ts
@@ -1,6 +1,8 @@
 import { ChildProcess } from "child_process";
 import spawn from "cross-spawn";
 import { Cancelable, debounce } from "lodash";
+import psTree from "pstree.remy";
+
 import { Executor } from "./types";
 
 interface LongRunningExecutorOptions {
@@ -31,9 +33,6 @@ export default class LongRunningExecutor implements Executor {
     this.isRunning = true;
     this.process = spawn(this.cmd, this.args as string[], {
       stdio: "inherit",
-      // Have all child processes in their own group.
-      // See `process.kill` below.
-      detached: true,
       shell: !this.args,
     });
 
@@ -51,18 +50,43 @@ export default class LongRunningExecutor implements Executor {
     });
   }
 
-  private restart(): void {
+  private async restart(): Promise<void> {
     this.shouldRestart = true;
-    // Using the `-` will kill all child procceses in the group.
-    // See: https://azimi.me/2014/12/31/kill-child_process-node-js.html
-    process.kill(-this.process!.pid, "SIGTERM");
+    return this.internalKill();
   }
 
-  private kill(): void {
+  private async kill(): Promise<void> {
     this.shouldRestart = false;
-    // Using the `-` will kill all child procceses in the group.
-    // See: https://azimi.me/2014/12/31/kill-child_process-node-js.html
-    process.kill(-this.process!.pid, "SIGTERM");
+    return this.internalKill();
+  }
+
+  private async internalKill(): Promise<void> {
+    return new Promise<void>((resolve, reject) => {
+      const signal = "SIGTERM";
+      if (process.platform === "win32") {
+        // Force kill (/F) the whole child tree (/T) by PID
+        spawn.sync("taskkill", [
+          "/pid",
+          this.process!.pid.toString(),
+          "/T",
+          "/F",
+        ]);
+        resolve();
+        return;
+      }
+
+      psTree(this.process!.pid, (err, kids) => {
+        if (err) {
+          reject(err);
+        }
+        spawn.sync("kill", [
+          `-${signal}`,
+          this.process!.pid.toString(),
+          ...kids.map(p => p.PID.toString()),
+        ]);
+        resolve();
+      });
+    });
   }
 
   // This is called before watching starts.
@@ -71,10 +95,10 @@ export default class LongRunningExecutor implements Executor {
   }
 
   // This is called before exiting.
-  public onCleanup() {
+  public async onCleanup() {
     this.restartDebounced.cancel();
     if (this.isRunning) {
-      this.kill();
+      await this.kill();
     }
   }
 
diff --git a/scripts/watcher/pstree.remy.d.ts b/scripts/watcher/pstree.remy.d.ts
new file mode 100644
index 000000000..4cca7eff8
--- /dev/null
+++ b/scripts/watcher/pstree.remy.d.ts
@@ -0,0 +1,6 @@
+declare module "pstree.remy" {
+  export default function psTree(
+    pid: number,
+    callback: (err: Error, kids: Array<{ PID: number }>) => void
+  ): void;
+}
diff --git a/scripts/watcher/types.ts b/scripts/watcher/types.ts
index 15bd6090b..89ed07a8d 100644
--- a/scripts/watcher/types.ts
+++ b/scripts/watcher/types.ts
@@ -13,7 +13,7 @@ export interface Watcher {
 
 export interface Executor {
   onInit?(): void;
-  onCleanup?(): void;
+  onCleanup?(): void | Promise<void>;
   execute(filePath: string): void;
 }
 
diff --git a/scripts/watcher/watch.ts b/scripts/watcher/watch.ts
index 8a3feac75..5c1825e30 100644
--- a/scripts/watcher/watch.ts
+++ b/scripts/watcher/watch.ts
@@ -32,10 +32,10 @@ function prependRootDir(prepend: string, cfg: WatchConfig): WatchConfig {
 
 function setupCleanup(config: Config) {
   ["SIGINT", "SIGTERM"].forEach(signal =>
-    process.once(signal as any, () => {
+    process.once(signal as any, async () => {
       for (const key of Object.keys(config.watchers)) {
         if (config.watchers[key].executor.onCleanup) {
-          config.watchers[key].executor.onCleanup!();
+          await config.watchers[key].executor.onCleanup!();
         }
       }
       process.exit(0);