diff --git a/packages/js/e2e-core-tests/index.js b/packages/js/e2e-core-tests/index.js
index e30dc29012b..9fd036edd21 100644
--- a/packages/js/e2e-core-tests/index.js
+++ b/packages/js/e2e-core-tests/index.js
@@ -2,6 +2,5 @@
  * Internal dependencies
  */
 const allSpecs = require( './specs' );
-const fs = require( 'fs' );
 
 module.exports = allSpecs;
diff --git a/packages/js/e2e-environment/bin/scaffold.js b/packages/js/e2e-environment/bin/scaffold.js
index ac74a756206..49d252f425e 100755
--- a/packages/js/e2e-environment/bin/scaffold.js
+++ b/packages/js/e2e-environment/bin/scaffold.js
@@ -5,6 +5,7 @@
  */
 const fs = require( 'fs' );
 const sprintf = require( 'sprintf-js' ).sprintf;
+const readlineSync = require( 'readline-sync' );
 
 /**
  * Internal dependencies.
@@ -18,6 +19,18 @@ const {
 const args = process.argv.slice( 2 );
 const [ command, packageName ] = args;
 
+/**
+ * Prompt the console for confirmation.
+ *
+ * @param {string} prompt Prompt for the user.
+ * @param {string} choices valid responses.
+ * @return {string}
+ */
+const confirm = ( prompt, choices ) => {
+	const answer = readlineSync.keyIn( prompt, choices );
+	return answer;
+};
+
 /**
  * Install the test scripts and sample default.json configuration
  */
@@ -49,11 +62,11 @@ if ( command == 'install' ) {
 		console.log( `Created sample test container initialization script to 'tests/e2e/${defaultInitName}'.` );
 	}
 
-	// Write test files
 	if ( ! testSpecs ) {
 		return;
 	}
 
+	// Write test files
 	const testsSpecFile = resolvePackagePath( testSpecs, pkg );
 	const specs = fs.readFileSync( testsSpecFile );
 	const tests = JSON.parse( specs );
@@ -82,6 +95,8 @@ if ( command == 'install' ) {
 		const eol = "\n";
 		const autoGenerate = sprintf( '/* This file was auto-generated by the command `npx wc-e2e install %s. */', packageName );
 		let importLineFormat;
+		let overwriteFiles;
+		let confirmPrompt;
 		if ( testFormat.toLowerCase() == 'cjs' ) {
 			importLineFormat = sprintf( "const {%%s} = require( '%s' );", pkg );
 		} else {
@@ -100,6 +115,11 @@ if ( command == 'install' ) {
 
 		// Loop through folders and files to write test scripts.
 		for ( let f = 0; f < active.length; f++ ) {
+			if ( overwriteFiles == 'q' ) {
+				overwriteFiles = '';
+				break;
+			}
+
 			const testFolder = active[ f ];
 			const { testFiles } = testFolder;
 
@@ -125,10 +145,21 @@ if ( command == 'install' ) {
 				const testFileName = `${specFolder}/${testFile.name}.${testExtension}`;
 				const testFilePath = resolveLocalE2ePath( testFileName );
 
-				// @todo Add check to see if file exists
-				// fs.existsSync
-				// @todo Confirm overwrite
-				// readline
+				// Check to see if file exists.
+				if ( fs.existsSync( testFilePath ) ) {
+					if ( overwriteFiles != 'a' ) {
+						confirmPrompt = `${testFileName} already exists. Overwrite? [Y]es/[n]o/[a]ll/[q]uit: `;
+						overwriteFiles = confirm( confirmPrompt, 'anqy' );
+						overwriteFiles = overwriteFiles.toLowerCase();
+					}
+
+					if ( overwriteFiles == 'q' ) {
+						break;
+					}
+					if ( overwriteFiles != 'a' && overwriteFiles != 'y' ) {
+						continue;
+					}
+				}
 
 				console.log( 'Writing tests/e2e/' + testFileName );
 				let buffer = [ autoGenerate ];
diff --git a/packages/js/e2e-environment/package.json b/packages/js/e2e-environment/package.json
index adc4f680866..c7005cb16c6 100644
--- a/packages/js/e2e-environment/package.json
+++ b/packages/js/e2e-environment/package.json
@@ -33,6 +33,7 @@
     "jest-each": "25.5.0",
     "jest-puppeteer": "^4.4.0",
     "node-stream-zip": "^1.13.6",
+	"readline-sync": "^1.4.10",
     "request": "^2.88.2",
     "sprintf-js": "^1.1.2"
   },
diff --git a/pnpm-lock.yaml b/pnpm-lock.yaml
index 7d9a5c0fb9b..9a39c20dbf2 100644
--- a/pnpm-lock.yaml
+++ b/pnpm-lock.yaml
@@ -129,6 +129,7 @@ importers:
       jest-puppeteer: ^4.4.0
       ndb: ^1.1.5
       node-stream-zip: ^1.13.6
+      readline-sync: ^1.4.10
       request: ^2.88.2
       semver: ^7.3.2
       sprintf-js: ^1.1.2
@@ -145,6 +146,7 @@ importers:
       jest-each: 25.5.0
       jest-puppeteer: 4.4.0
       node-stream-zip: 1.15.0
+      readline-sync: 1.4.10
       request: 2.88.2
       sprintf-js: 1.1.2
     devDependencies:
@@ -18063,6 +18065,11 @@ packages:
     dependencies:
       picomatch: 2.3.0
 
+  /readline-sync/1.4.10:
+    resolution: {integrity: sha512-gNva8/6UAe8QYepIQH/jQ2qn91Qj0B9sYjMBBs3QOB8F2CXcKgLxQaJRP76sWVRQt+QU+8fAkCbCvjjMFu7Ycw==}
+    engines: {node: '>= 0.8.0'}
+    dev: false
+
   /realpath-native/1.1.0:
     resolution: {integrity: sha512-wlgPA6cCIIg9gKz0fgAPjnzh4yR/LnXovwuo9hvyGvx3h8nX4+/iLZplfUWasXpqD8BdnGnP5njOFjkUwPzvjA==}
     engines: {node: '>=4'}