diff --git a/.github/workflows/techdocs-e2e.yml b/.github/workflows/techdocs-e2e.yml
index 8f166515ff..191274ec84 100644
--- a/.github/workflows/techdocs-e2e.yml
+++ b/.github/workflows/techdocs-e2e.yml
@@ -39,4 +39,4 @@ jobs:
 
       - name: techdocs-cli e2e test
         working-directory: packages/techdocs-cli
-        run: yarn test:e2e
+        run: yarn test:e2e:ci
diff --git a/packages/techdocs-cli/package.json b/packages/techdocs-cli/package.json
index 0f18903282..a24a1be0f8 100644
--- a/packages/techdocs-cli/package.json
+++ b/packages/techdocs-cli/package.json
@@ -24,8 +24,9 @@
     "build": "./scripts/build.sh",
     "clean": "backstage-cli clean",
     "lint": "backstage-cli lint",
-    "test": "backstage-cli test --testPathIgnorePatterns src/e2e.test.ts",
-    "test:e2e": "backstage-cli test --testPathPattern src/e2e.test.ts --runInBand"
+    "test": "backstage-cli test --testPathIgnorePatterns=src/e2e.test.ts",
+    "test:e2e": "backstage-cli test src/e2e.test.ts",
+    "test:e2e:ci": "backstage-cli test --watchAll=false --ci src/e2e.test.ts"
   },
   "bin": {
     "techdocs-cli": "bin/techdocs-cli"
@@ -41,6 +42,7 @@
     "@types/serve-handler": "^6.1.0",
     "@types/webpack-env": "^1.15.3",
     "embedded-techdocs-app": "0.0.0",
+    "find-process": "^1.4.5",
     "nodemon": "^2.0.2",
     "ts-node": "^10.0.0"
   },
diff --git a/packages/techdocs-cli/src/commands/serve/serve.ts b/packages/techdocs-cli/src/commands/serve/serve.ts
index 5fed2dd56e..1182c850b3 100644
--- a/packages/techdocs-cli/src/commands/serve/serve.ts
+++ b/packages/techdocs-cli/src/commands/serve/serve.ts
@@ -121,10 +121,5 @@ export default async function serve(cmd: Command) {
       );
     });
 
-  try {
-    await waitForSignal([mkdocsChildProcess]);
-    process.exit(0);
-  } catch {
-    process.exit(1);
-  }
+  await waitForSignal([mkdocsChildProcess]);
 }
diff --git a/packages/techdocs-cli/src/e2e.test.ts b/packages/techdocs-cli/src/e2e.test.ts
index e6cf4e84c5..088dbc44b8 100644
--- a/packages/techdocs-cli/src/e2e.test.ts
+++ b/packages/techdocs-cli/src/e2e.test.ts
@@ -14,13 +14,15 @@
  * limitations under the License.
  */
 
-import { execSync, spawn } from 'child_process';
+import { execSync, spawn, SpawnOptionsWithoutStdio } from 'child_process';
 import path from 'path';
 
+import findProcess from 'find-process';
+
 const executeCommand = (
   command: string,
   args: string[],
-  options?: Object,
+  options?: SpawnOptionsWithoutStdio,
 ): Promise<{
   exit: number;
   stdout: string;
@@ -29,10 +31,9 @@ const executeCommand = (
   return new Promise(resolve => {
     const stdout: Buffer[] = [];
     const stderr: Buffer[] = [];
-    const proc =
-      process.platform === 'win32'
-        ? spawn('cmd', ['/s', '/c', command, ...args], options)
-        : spawn(command, args, options);
+
+    const shell = process.platform === 'win32';
+    const proc = spawn(command, args, { ...options, shell });
 
     proc.stdout?.on('data', data => {
       stdout.push(Buffer.from(data));
@@ -52,9 +53,25 @@ const executeCommand = (
   });
 };
 
+const timeout = 25000;
+
+jest.setTimeout(timeout * 2);
+
 describe('end-to-end', () => {
   const cwd = path.resolve(__dirname, 'fixture');
 
+  afterEach(async () => {
+    // On Windows the pid of a spawned process may be wrong
+    // Because of this, we should be kill the MKDocs after the test
+    // (e.g. https://github.com/nodejs/node/issues/4289#issuecomment-854270414)
+    if (process.platform === 'win32') {
+      const procs = await findProcess('name', 'mkdocs', true);
+      procs.forEach((proc: { pid: number }) => {
+        process.kill(proc.pid);
+      });
+    }
+  });
+
   beforeAll(() => {
     execSync('yarn workspace @techdocs/cli link', { stdio: 'ignore' });
   });
@@ -64,29 +81,26 @@ describe('end-to-end', () => {
   });
 
   it('shows help text', async () => {
-    jest.setTimeout(30000);
     const proc = await executeCommand('techdocs-cli', ['--help']);
     expect(proc.stdout).toContain('Usage: techdocs-cli [options]');
     expect(proc.exit).toEqual(0);
   });
 
   it('can generate', async () => {
-    jest.setTimeout(30000);
     const proc = await executeCommand(
       'techdocs-cli',
       ['generate', '--no-docker'],
-      { cwd, timeout: 25000 },
+      { cwd, timeout },
     );
     expect(proc.stdout).toContain('Successfully generated docs');
     expect(proc.exit).toEqual(0);
   });
 
   it('can serve in mkdocs', async () => {
-    jest.setTimeout(30000);
     const proc = await executeCommand(
       'techdocs-cli',
       ['serve:mkdocs', '--no-docker'],
-      { cwd, timeout: 25000 },
+      { cwd, timeout },
     );
     expect(proc.stdout).toContain('Starting mkdocs server');
     expect(proc.exit).toEqual(0);
@@ -97,7 +111,7 @@ describe('end-to-end', () => {
     const proc = await executeCommand(
       'techdocs-cli',
       ['serve', '--no-docker'],
-      { cwd, timeout: 25000 },
+      { cwd, timeout },
     );
     expect(proc.stdout).toContain('Starting mkdocs server');
     expect(proc.stdout).toContain('Serving docs in Backstage at');
diff --git a/scripts/techdocs-cli.js b/scripts/techdocs-cli.js
index 90dcc40f39..7cc07f15fa 100644
--- a/scripts/techdocs-cli.js
+++ b/scripts/techdocs-cli.js
@@ -19,7 +19,7 @@ const { execSync } = require('child_process');
 
 const args = process.argv.slice(2);
 
-execSync(`yarn workspace @techdocs/cli build`, { stdio: 'inherit' });
+execSync(`yarn -s workspace @techdocs/cli build`, { stdio: 'inherit' });
 execSync(`yarn workspace @techdocs/cli link`, { stdio: 'ignore' });
 execSync(`techdocs-cli ${args.join(' ')}`, { stdio: 'inherit' });
 execSync(`yarn workspace @techdocs/cli unlink`, { stdio: 'ignore' });
diff --git a/yarn.lock b/yarn.lock
index f51a95fccd..b52b045573 100644
--- a/yarn.lock
+++ b/yarn.lock
@@ -14667,6 +14667,15 @@ find-my-way@^2.2.2:
     safe-regex2 "^2.0.0"
     semver-store "^0.3.0"
 
+find-process@^1.4.5:
+  version "1.4.5"
+  resolved "https://registry.npmjs.org/find-process/-/find-process-1.4.5.tgz#6a0e4c87a32ca927c05cbed7b9078d62ffaac1a4"
+  integrity sha512-v11rJYYISUWn+s8qZzgGnBvlzRKf3bOtlGFM8H0kw56lGQtOmLuLCzuclA5kehA2j7S5sioOWdI4woT3jDavAw==
+  dependencies:
+    chalk "^4.0.0"
+    commander "^5.1.0"
+    debug "^4.1.1"
+
 find-root@^1.1.0:
   version "1.1.0"
   resolved "https://registry.npmjs.org/find-root/-/find-root-1.1.0.tgz#abcfc8ba76f708c42a97b3d685b7e9450bfb9ce4"