diff --git a/.gitignore b/.gitignore
index 3c508998a3f..cac442b27ff 100644
--- a/.gitignore
+++ b/.gitignore
@@ -54,3 +54,4 @@ packages/**/*.map
 
 # temporary test files
 test-assets/
+
diff --git a/package.json b/package.json
index 254364233b2..d3bb59c00f9 100644
--- a/package.json
+++ b/package.json
@@ -104,6 +104,7 @@
     "chalk": "^3.0.0",
     "commitlint": "^8.3.5",
     "commitlint-config-cz": "^0.13.0",
+    "concat-stream": "^2.0.0",
     "cz-customizable": "^6.2.0",
     "del-cli": "^3.0.0",
     "eslint": "^6.8.0",
diff --git a/packages/webpack-cli/.gitignore b/packages/webpack-cli/.gitignore
index 6cdf0169865..39454064e96 100644
--- a/packages/webpack-cli/.gitignore
+++ b/packages/webpack-cli/.gitignore
@@ -47,3 +47,7 @@ junit.xml
 
 #typescript source maps
 packages/**/*.map
+
+# ignore scaffolded files due to tests of init
+__tests__/init/*
+!__tests__/init/**/*.test.js
diff --git a/packages/webpack-cli/__tests__/init/auto/init-auto.test.js b/packages/webpack-cli/__tests__/init/auto/init-auto.test.js
new file mode 100644
index 00000000000..408c7ae5cd2
--- /dev/null
+++ b/packages/webpack-cli/__tests__/init/auto/init-auto.test.js
@@ -0,0 +1,31 @@
+/* eslint-disable node/no-unpublished-require */
+'use strict';
+
+const firstPrompt = 'Will your application have multiple bundles?';
+const fs = require('fs');
+const { join } = require('path');
+const { run } = require('../../../../../test/utils/test-utils');
+
+jest.setTimeout(200000);
+describe('init auto flag', () => {
+    it('should prompt with w/o auto flag', () => {
+        const { stdout, stderr } = run(__dirname, ['init'], false);
+        expect(stdout).toBeTruthy();
+        expect(stderr).toBeFalsy();
+        expect(stdout).toContain(firstPrompt);
+    });
+
+    it('should scaffold and not prompt with auto flag', () => {
+        const { stdout } = run(__dirname, ['init', '--auto'], false);
+        // Test no prompts are present
+        expect(stdout).toBeTruthy();
+        expect(stdout).not.toContain(firstPrompt);
+
+        // Test regressively files are scaffolded
+        const files = ['./sw.js', './package.json', './yarn.lock', './src/index.js'];
+        // eslint-disable-next-line prettier/prettier
+        files.forEach((file) => {
+            expect(fs.existsSync(join(__dirname, file))).toBeTruthy();
+        });
+    });
+});
diff --git a/packages/webpack-cli/__tests__/init/coreFlags/init-flags.test.js b/packages/webpack-cli/__tests__/init/coreFlags/init-flags.test.js
new file mode 100644
index 00000000000..3ca1f7c73ab
--- /dev/null
+++ b/packages/webpack-cli/__tests__/init/coreFlags/init-flags.test.js
@@ -0,0 +1,15 @@
+/* eslint-disable node/no-unpublished-require */
+'use strict';
+
+const firstPrompt = 'Will your application have multiple bundles?';
+const { run } = require('../../../../../test/utils/test-utils');
+
+describe('init with core flags', () => {
+    it('should output help with --help flag', () => {
+        const { stdout, stderr } = run(__dirname, ['init', '--help'], false);
+        expect(stdout).toBeTruthy();
+        expect(stderr).toBeFalsy();
+        expect(stdout).not.toContain(firstPrompt);
+        expect(stdout).toContain('Initialize a new webpack configuration');
+    });
+});
diff --git a/packages/webpack-cli/__tests__/init/generator/init-inquirer.test.js b/packages/webpack-cli/__tests__/init/generator/init-inquirer.test.js
new file mode 100644
index 00000000000..d554ccecb1e
--- /dev/null
+++ b/packages/webpack-cli/__tests__/init/generator/init-inquirer.test.js
@@ -0,0 +1,27 @@
+/* eslint-disable node/no-unpublished-require */
+'use strict';
+
+const fs = require('fs');
+const path = require('path');
+const { runInitWithAnswers } = require('../../../../../test/utils/test-utils');
+const firstPrompt = 'Will your application have multiple bundles?';
+
+const ENTER = '\x0D';
+
+jest.setTimeout(200000);
+
+describe('init', () => {
+    it('should scaffold when given answers', async () => {
+        const stdout = await runInitWithAnswers(__dirname, ['N', ENTER, ENTER, ENTER, ENTER, ENTER, ENTER, ENTER]);
+
+        expect(stdout).toBeTruthy();
+        expect(stdout).toContain(firstPrompt);
+
+        // Test regressively files are scaffolded
+        const files = ['./sw.js', './package.json', './yarn.lock', './src/index.js'];
+        // eslint-disable-next-line prettier/prettier
+        files.forEach((file) => {
+            expect(fs.existsSync(path.join(__dirname, file))).toBeTruthy();
+        });
+    });
+});
diff --git a/test/utils/test-utils.js b/test/utils/test-utils.js
index a9cb59769a2..fb7418dc78f 100644
--- a/test/utils/test-utils.js
+++ b/test/utils/test-utils.js
@@ -4,6 +4,8 @@ const fs = require('fs');
 const execa = require('execa');
 const { sync: spawnSync } = execa;
 const { Writable } = require('readable-stream');
+const concat = require('concat-stream');
+
 const WEBPACK_PATH = path.resolve(__dirname, '../../packages/webpack-cli/bin/cli.js');
 const ENABLE_LOG_COMPILATION = process.env.ENABLE_PIPE || false;
 
@@ -79,6 +81,39 @@ function runAndGetWatchProc(testCase, args = [], setOutput = true) {
 
     return webpackProc;
 }
+/**
+ * runInitWithAnswers
+ * @param {string} location location of current working directory
+ * @param {string[]} answers answers to be passed to stdout for inquirer question
+ */
+const runInitWithAnswers = async (location, answers) => {
+    const runner = runAndGetWatchProc(location, ['init'], false);
+    runner.stdin.setDefaultEncoding('utf-8');
+
+    // Simulate answers by sending the answers after waiting for 2s
+    const simulateAnswers = answers.reduce((prevAnswer, answer) => {
+        return prevAnswer.then(() => {
+            return new Promise((resolvePromise) => {
+                setTimeout(() => {
+                    runner.stdin.write(answer);
+                    resolvePromise();
+                }, 2000);
+            });
+        });
+    }, Promise.resolve());
+
+    await simulateAnswers.then(() => {
+        runner.stdin.end();
+    });
+
+    return new Promise((resolve) => {
+        runner.stdout.pipe(
+            concat((result) => {
+                resolve(result.toString());
+            }),
+        );
+    });
+};
 
 function extractSummary(stdout) {
     if (stdout === '') {
@@ -205,6 +240,7 @@ module.exports = {
     runServe,
     runAndGetWatchProc,
     extractSummary,
+    runInitWithAnswers,
     appendDataIfFileExists,
     copyFile,
     copyFileAsync,