diff --git a/packages/webpack-cli/__tests__/serve/serve.test.js b/packages/webpack-cli/__tests__/serve/serve.test.js
index 007cff90e95..edebe9bd2a5 100644
--- a/packages/webpack-cli/__tests__/serve/serve.test.js
+++ b/packages/webpack-cli/__tests__/serve/serve.test.js
@@ -14,14 +14,14 @@ describe('Serve', () => {
     it('should run with cli', async () => {
         const { stdout, stderr } = await runServe([], __dirname);
         expect(stdout).toContain('main.js');
-        expect(stdout).not.toContain('hot/dev-server.js');
+        expect(stdout).not.toContain('HotModuleReplacementPlugin');
         expect(stderr).toHaveLength(0);
     });
 
     it('should work with flags', async () => {
         const { stdout, stderr } = await runServe(['--hot'], __dirname);
         expect(stdout).toContain('main.js');
-        expect(stdout).toContain('hot/dev-server.js');
+        expect(stdout).toContain('HotModuleReplacementPlugin');
         expect(stderr).toHaveLength(0);
     });
 });
diff --git a/packages/webpack-cli/__tests__/serve/webpack.config.js b/packages/webpack-cli/__tests__/serve/webpack.config.js
index 955bbdd3364..ef02e82b858 100644
--- a/packages/webpack-cli/__tests__/serve/webpack.config.js
+++ b/packages/webpack-cli/__tests__/serve/webpack.config.js
@@ -1,4 +1,8 @@
+// eslint-disable-next-line node/no-unpublished-require
+const WebpackCLITestPlugin = require('../../../../test/utils/webpack-cli-test-plugin');
+
 module.exports = {
     mode: 'development',
     devtool: false,
+    plugins: [new WebpackCLITestPlugin(['plugins'], false)],
 };
diff --git a/packages/webpack-cli/lib/groups/HelpGroup.js b/packages/webpack-cli/lib/groups/HelpGroup.js
index a640df64083..9ea63428eff 100644
--- a/packages/webpack-cli/lib/groups/HelpGroup.js
+++ b/packages/webpack-cli/lib/groups/HelpGroup.js
@@ -117,6 +117,11 @@ class HelpGroup {
                 optionList: options.core
                     .map((e) => {
                         if (e.type.length > 1) e.type = e.type[0];
+                        // Here we replace special characters with chalk's escape
+                        // syntax (`\$&`) to avoid chalk trying to re-process our input.
+                        // This is needed because chalk supports a form of `{var}`
+                        // interpolation.
+                        e.description = e.description.replace(/[{}\\]/g, '\\$&');
                         return e;
                     })
                     .concat(negatedFlags),
diff --git a/test/config-name/config-name.test.js b/test/config-name/config-name.test.js
index 53b66537ecf..dfc9c8ba805 100644
--- a/test/config-name/config-name.test.js
+++ b/test/config-name/config-name.test.js
@@ -8,9 +8,9 @@ describe('--config-name flag', () => {
     it('should select only the config whose name is passed with --config-name', (done) => {
         const { stderr, stdout } = run(__dirname, ['--config-name', 'first'], false);
         expect(stderr).toBeFalsy();
-        expect(stdout).toContain('Child first');
-        expect(stdout).not.toContain('Child second');
-        expect(stdout).not.toContain('Child third');
+        expect(stdout).toContain('first');
+        expect(stdout).not.toContain('second');
+        expect(stdout).not.toContain('third');
 
         stat(resolve(__dirname, './dist/dist-first.js'), (err, stats) => {
             expect(err).toBe(null);
@@ -22,9 +22,9 @@ describe('--config-name flag', () => {
     it('should work with multiple values for --config-name', (done) => {
         const { stderr, stdout } = run(__dirname, ['--config-name', 'first', '--config-name', 'third'], false);
         expect(stderr).toBeFalsy();
-        expect(stdout).toContain('Child first');
-        expect(stdout).not.toContain('Child second');
-        expect(stdout).toContain('Child third');
+        expect(stdout).toContain('first');
+        expect(stdout).not.toContain('second');
+        expect(stdout).toContain('third');
 
         stat(resolve(__dirname, './dist/dist-first.js'), (err, stats) => {
             expect(err).toBe(null);
diff --git a/test/config/defaults/basic-config/default-js-config.test.js b/test/config/defaults/basic-config/default-js-config.test.js
index 785a6e02078..259fc8ee21d 100644
--- a/test/config/defaults/basic-config/default-js-config.test.js
+++ b/test/config/defaults/basic-config/default-js-config.test.js
@@ -1,6 +1,6 @@
 const fs = require('fs');
 const path = require('path');
-const { run } = require('../../../utils/test-utils');
+const { run, isWebpack5 } = require('../../../utils/test-utils');
 
 describe('Zero Config', () => {
     it('runs when config is present but not supplied via flag', () => {
@@ -8,11 +8,13 @@ describe('Zero Config', () => {
         // default entry should be used
         expect(stdout).toContain('./index.js');
         // should pick up the output path from config
-        expect(stdout).toContain('Entrypoint main = test-output');
-        expect(stdout).toContain('Hash');
-        expect(stdout).toContain('Version');
-        expect(stdout).toContain('Built at');
-        expect(stdout).toContain('Time');
+        expect(stdout).toContain('test-output');
+        if (!isWebpack5) {
+            expect(stdout).toContain('Hash');
+            expect(stdout).toContain('Version');
+            expect(stdout).toContain('Built at');
+            expect(stdout).toContain('Time');
+        }
         // Should return the correct exit code
         expect(exitCode).toEqual(0);
         // check that the output file exists
diff --git a/test/config/defaults/cjs-config/default-cjs-config.test.js b/test/config/defaults/cjs-config/default-cjs-config.test.js
index 0adda400566..f64365e369e 100644
--- a/test/config/defaults/cjs-config/default-cjs-config.test.js
+++ b/test/config/defaults/cjs-config/default-cjs-config.test.js
@@ -1,6 +1,6 @@
 const fs = require('fs');
 const path = require('path');
-const { run } = require('../../../utils/test-utils');
+const { run, isWebpack5 } = require('../../../utils/test-utils');
 
 describe('Default Config:', () => {
     it('Should be able to pick cjs config by default', () => {
@@ -8,11 +8,13 @@ describe('Default Config:', () => {
         // default entry should be used
         expect(stdout).toContain('./index.js');
         // should pick up the output path from config
-        expect(stdout).toContain('Entrypoint main = test-output');
-        expect(stdout).toContain('Hash');
-        expect(stdout).toContain('Version');
-        expect(stdout).toContain('Built at');
-        expect(stdout).toContain('Time');
+        expect(stdout).toContain('test-output');
+        if (!isWebpack5) {
+            expect(stdout).toContain('Hash');
+            expect(stdout).toContain('Version');
+            expect(stdout).toContain('Built at');
+            expect(stdout).toContain('Time');
+        }
         // Should return the correct exit code
         expect(exitCode).toEqual(0);
         // check that the output file exists
diff --git a/test/config/multiple/multiple-config.test.js b/test/config/multiple/multiple-config.test.js
index f040031bdbc..dedf892b115 100644
--- a/test/config/multiple/multiple-config.test.js
+++ b/test/config/multiple/multiple-config.test.js
@@ -9,8 +9,8 @@ describe('Multiple config flag: ', () => {
         // Should contain the correct exit code
         expect(exitCode).toEqual(0);
         // Should spawn multiple compilers
-        expect(stdout).toContain('Child amd:');
-        expect(stdout).toContain('Child commonjs:');
+        expect(stdout).toContain('amd:');
+        expect(stdout).toContain('commonjs:');
 
         expect(stderr).toBeFalsy();
 
diff --git a/test/core-flags/output-flags.test.js b/test/core-flags/output-flags.test.js
index 93a9c79c606..7bda29b938f 100644
--- a/test/core-flags/output-flags.test.js
+++ b/test/core-flags/output-flags.test.js
@@ -8,7 +8,10 @@ const outputFlags = flagsFromCore.filter(({ name }) => name.startsWith('output-'
 describe('output config related flag', () => {
     outputFlags.forEach((flag) => {
         // extract property name from flag name
-        const property = flag.name.split('output-')[1];
+        let property = flag.name.split('output-')[1];
+        if (property.includes('environment-')) {
+            property = property.split('environment-')[1];
+        }
         const propName = hyphenToUpperCase(property);
 
         if (flag.type === Boolean && !flag.name.includes('output-library')) {
@@ -32,9 +35,13 @@ describe('output config related flag', () => {
             it(`should config --no-${flag.name} correctly`, () => {
                 const { stderr, stdout } = run(__dirname, [`--no-${flag.name}`]);
 
-                if (flag.name === 'output-enabled-chunk-loading-types-reset') {
+                if (flag.name.includes('loading-types-reset')) {
                     expect(stderr).toBeFalsy();
-                    expect(stdout).toContain(`enabledChunkLoadingTypes: [ 'jsonp' ]`);
+                    if (flag.name === 'output-enabled-wasm-loading-types-reset') {
+                        expect(stdout).toContain(`enabledWasmLoadingTypes: [ 'fetch' ]`);
+                    } else {
+                        expect(stdout).toContain(`enabledChunkLoadingTypes: [ 'jsonp', 'import-scripts' ]`);
+                    }
                 } else if (flag.name.includes('-reset')) {
                     const option = propName.split('Reset')[0];
                     expect(stderr).toBeFalsy();
@@ -76,7 +83,7 @@ describe('output config related flag', () => {
                     stdout = run(__dirname, [`--${flag.name}`, 'jsonp']).stdout;
 
                     expect(stdout).toContain(`${propName}: 'jsonp'`);
-                } else if (flag.name === 'output-enabled-chunk-loading-types') {
+                } else if (flag.name === 'output-enabled-chunk-loading-types' || flag.name === 'output-enabled-wasm-loading-types') {
                     stdout = run(__dirname, [`--${flag.name}`, 'async-node']).stdout;
 
                     expect(stdout).toContain(`${propName}: [ 'async-node' ]`);
@@ -103,6 +110,18 @@ describe('output config related flag', () => {
                     expect(stdout).toContain(`${propName}: [ 'var' ]`);
                 } else if (flag.name === 'output-path') {
                     expect(stdout).toContain('test');
+                } else if (flag.name === 'output-worker-chunk-loading') {
+                    stdout = run(__dirname, [`--${flag.name}`, 'async-node']).stdout;
+                    expect(stdout).toContain(`${propName}: 'async-node'`);
+                } else if (flag.name === 'output-worker-chunk-loading') {
+                    stdout = run(__dirname, [`--${flag.name}`, 'async-node']).stdout;
+                    expect(stdout).toContain(`${propName}: 'async-node'`);
+                } else if (flag.name === 'output-chunk-format') {
+                    stdout = run(__dirname, [`--${flag.name}`, 'commonjs']).stdout;
+                    expect(stdout).toContain(`${propName}: 'commonjs'`);
+                } else if (flag.name.includes('wasm')) {
+                    stdout = run(__dirname, [`--${flag.name}`, 'async-node']).stdout;
+                    expect(stdout).toContain(`${propName}: 'async-node'`);
                 } else {
                     expect(stderr).toBeFalsy();
                     expect(stdout).toContain(`${propName}: 'test'`);
diff --git a/test/core-flags/stats-flags.test.js b/test/core-flags/stats-flags.test.js
index c4033cf5ef7..be141e097e3 100644
--- a/test/core-flags/stats-flags.test.js
+++ b/test/core-flags/stats-flags.test.js
@@ -59,6 +59,9 @@ describe('stats config related flag', () => {
                     expect(stdout).toContain(`stats: { ${propName}: 'log' }`);
                 } else if (flag.name === 'stats-context') {
                     expect(stdout).toContain('log');
+                } else if (flag.name === 'stats-entrypoints') {
+                    stdout = run(__dirname, [`--${flag.name}`, 'auto']).stdout;
+                    expect(stdout).toContain(`stats: { ${propName}: 'auto' }`);
                 } else {
                     expect(stdout).toContain(`stats: { ${propName}: [ 'log' ] }`);
                 }
diff --git a/test/serve/basic/serve-basic.test.js b/test/serve/basic/serve-basic.test.js
index 67f39c94d36..b7ff5d2c847 100644
--- a/test/serve/basic/serve-basic.test.js
+++ b/test/serve/basic/serve-basic.test.js
@@ -38,35 +38,35 @@ describe('basic serve usage', () => {
     it('should not invoke info subcommand', async () => {
         const { stdout, stderr } = await runServe(['--client-log-level', 'info'], testPath);
         expect(stdout).toContain('main.js');
-        expect(stdout).not.toContain('hot/dev-server.js');
+        expect(stdout).not.toContain('HotModuleReplacementPlugin');
         expect(stderr).toHaveLength(0);
     });
 
     it('compiles without flags', async () => {
         const { stdout, stderr } = await runServe(['--port', port], testPath);
         expect(stdout).toContain('main.js');
-        expect(stdout).not.toContain('hot/dev-server.js');
+        expect(stdout).not.toContain('HotModuleReplacementPlugin');
         expect(stderr).toHaveLength(0);
     });
 
     it('uses hot flag to alter bundle', async () => {
         const { stdout, stderr } = await runServe(['--port', port, '--hot'], testPath);
         expect(stdout).toContain('main.js');
-        expect(stdout).toContain('hot/dev-server.js');
+        expect(stdout).toContain('HotModuleReplacementPlugin');
         expect(stderr).toHaveLength(0);
     });
 
     it('uses no-hot flag', async () => {
         const { stdout, stderr } = await runServe(['--port', port, '--no-hot'], testPath);
         expect(stdout).toContain('main.js');
-        expect(stdout).not.toContain('hot/dev-server.js');
+        expect(stdout).not.toContain('HotModuleReplacementPlugin');
         expect(stderr).toHaveLength(0);
     });
 
     it('uses hot flag and progress flag', async () => {
         const { stdout, stderr } = await runServe(['--port', port, '--hot', '--progress'], testPath);
         expect(stdout).toContain('main.js');
-        expect(stdout).toContain('hot/dev-server.js');
+        expect(stdout).toContain('HotModuleReplacementPlugin');
         // progress flag makes use of stderr
         expect(stderr).not.toHaveLength(0);
     });
diff --git a/test/serve/basic/webpack.config.js b/test/serve/basic/webpack.config.js
index 955bbdd3364..8fdd96a616b 100644
--- a/test/serve/basic/webpack.config.js
+++ b/test/serve/basic/webpack.config.js
@@ -1,4 +1,8 @@
+// eslint-disable-next-line node/no-unpublished-require
+const WebpackCLITestPlugin = require('../../utils/webpack-cli-test-plugin');
+
 module.exports = {
     mode: 'development',
     devtool: false,
+    plugins: [new WebpackCLITestPlugin(['plugins'], false)],
 };
diff --git a/test/serve/with-custom-port/serve-custom-config.test.js b/test/serve/with-custom-port/serve-custom-config.test.js
index 15088616b6a..e0e0b55e8fb 100644
--- a/test/serve/with-custom-port/serve-custom-config.test.js
+++ b/test/serve/with-custom-port/serve-custom-config.test.js
@@ -27,7 +27,7 @@ describe('serve with devServer in config', () => {
         const { stdout, stderr } = await runServe([], testPath);
         // Should output the correct bundle file
         expect(stdout).toContain('main.js');
-        expect(stdout).not.toContain('hot/dev-server.js');
+        expect(stdout).not.toContain('HotModuleReplacementPlugin');
         // Runs at correct host and port
         expect(stdout).toContain('http://0.0.0.0:1234');
         expect(stderr).toBeFalsy();
@@ -37,7 +37,7 @@ describe('serve with devServer in config', () => {
         const { stdout, stderr } = await runServe(['--port', port], testPath);
         // Should output the correct bundle file
         expect(stdout).toContain('main.js');
-        expect(stdout).not.toContain('hot/dev-server.js');
+        expect(stdout).not.toContain('HotModuleReplacementPlugin');
         // Runs at correct host and port
         expect(stdout).toContain(`http://0.0.0.0:${port}`);
         expect(stderr).toBeFalsy();
@@ -48,7 +48,7 @@ describe('serve with devServer in config', () => {
         // Should output the correct bundle file
         expect(stdout).toContain('main.js');
         // HMR is being used
-        expect(stdout).toContain('hot/dev-server.js');
+        expect(stdout).toContain('HotModuleReplacementPlugin');
         // Runs at correct host and port
         expect(stdout).toContain(`http://0.0.0.0:${port}`);
         expect(stderr).toBeFalsy();
@@ -59,7 +59,7 @@ describe('serve with devServer in config', () => {
         // Should output the correct bundle file
         expect(stdout).toContain('main.js');
         // HMR is not being used
-        expect(stdout).not.toContain('hot/dev-server.js');
+        expect(stdout).not.toContain('HotModuleReplacementPlugin');
         // Runs at correct host and port
         expect(stdout).toContain(`http://0.0.0.0:${port}`);
         expect(stderr).toBeFalsy();
diff --git a/test/serve/with-custom-port/webpack.config.js b/test/serve/with-custom-port/webpack.config.js
index d031e6a24ee..3121fcb10ad 100644
--- a/test/serve/with-custom-port/webpack.config.js
+++ b/test/serve/with-custom-port/webpack.config.js
@@ -1,3 +1,6 @@
+// eslint-disable-next-line node/no-unpublished-require
+const WebpackCLITestPlugin = require('../../utils/webpack-cli-test-plugin');
+
 module.exports = {
     mode: 'development',
     devtool: false,
@@ -5,4 +8,5 @@ module.exports = {
         port: 1234,
         host: '0.0.0.0',
     },
+    plugins: [new WebpackCLITestPlugin(['plugins'], false)],
 };
diff --git a/test/stats/cli-flags/stats.test.js b/test/stats/cli-flags/stats.test.js
index d2aa7277e91..83cd0cc0f9c 100644
--- a/test/stats/cli-flags/stats.test.js
+++ b/test/stats/cli-flags/stats.test.js
@@ -1,8 +1,7 @@
 /* eslint-disable node/no-extraneous-require */
 /* eslint-disable node/no-unpublished-require */
 'use strict';
-const { run } = require('../../utils/test-utils');
-const { version } = require('webpack');
+const { run, isWebpack5 } = require('../../utils/test-utils');
 
 const presets = ['normal', 'detailed', 'errors-only', 'errors-warnings', 'minimal', 'verbose', 'none'];
 
@@ -11,7 +10,7 @@ describe('stats flag', () => {
         it(`should accept --stats "${preset}"`, () => {
             const { stderr, stdout } = run(__dirname, ['--stats', `${preset}`]);
             expect(stderr).toBeFalsy();
-            if (version.startsWith('5')) {
+            if (isWebpack5) {
                 expect(stdout).toContain(`stats: { preset: '${preset}' }`);
             } else {
                 expect(stdout).toContain(`stats: '${preset}'`);
@@ -22,7 +21,7 @@ describe('stats flag', () => {
     it('should accept stats as boolean', () => {
         const { stderr, stdout } = run(__dirname, ['--stats']);
         expect(stderr).toBeFalsy();
-        if (version.startsWith('5')) {
+        if (isWebpack5) {
             expect(stdout).toContain(`stats: { preset: 'normal' }`);
         } else {
             expect(stdout).toContain('stats: true');
@@ -33,7 +32,13 @@ describe('stats flag', () => {
         const { stderr, stdout } = run(__dirname, ['--stats', 'foo']);
         expect(stderr).toBeTruthy();
         expect(stderr).toContain('* configuration.stats should be one of these:');
-        expect(stderr).toContain('"none" | "errors-only" | "minimal" | "normal" | "detailed" | "verbose" | "errors-warnings"');
+        if (isWebpack5) {
+            expect(stderr).toContain(
+                `"none" | "summary" | "errors-only" | "errors-warnings" | "minimal" | "normal" | "detailed" | "verbose"`,
+            );
+        } else {
+            expect(stderr).toContain('"none" | "errors-only" | "minimal" | "normal" | "detailed" | "verbose" | "errors-warnings"');
+        }
         expect(stdout).toBeTruthy();
     });
 });
diff --git a/test/target/flag-test/target-flag.test.js b/test/target/flag-test/target-flag.test.js
index 3a300d692bb..899bf401f98 100644
--- a/test/target/flag-test/target-flag.test.js
+++ b/test/target/flag-test/target-flag.test.js
@@ -1,7 +1,7 @@
 'use strict';
 const { stat } = require('fs');
 const { resolve } = require('path');
-const { run } = require('../../utils/test-utils');
+const { run, isWebpack5 } = require('../../utils/test-utils');
 
 const targetValues = ['web', 'webworker', 'node', 'async-node', 'node-webkit', 'electron-main', 'electron-renderer', 'electron-preload'];
 
@@ -34,6 +34,10 @@ describe('--target flag', () => {
 
     it(`should throw error with invalid value for --target`, () => {
         const { stderr } = run(__dirname, ['--target', 'invalid']);
-        expect(stderr).toContain('Invalid configuration object');
+        if (isWebpack5) {
+            expect(stderr).toContain(`Error: Unknown target 'invalid'`);
+        } else {
+            expect(stderr).toContain('Invalid configuration object');
+        }
     });
 });
diff --git a/test/utils/cli-plugin-test/plugin.test.js b/test/utils/cli-plugin-test/plugin.test.js
index 8bbf2687701..96a5ff20c27 100644
--- a/test/utils/cli-plugin-test/plugin.test.js
+++ b/test/utils/cli-plugin-test/plugin.test.js
@@ -10,6 +10,6 @@ describe('webpack-cli-test-plugin Test', () => {
         if (typeof cli !== 'undefined') {
             expect(stdout).toContain(`alias: { alias: [ 'alias1', 'alias2' ] }`);
         }
-        expect(stdout).toContain('plugins: [ WebpackCLITestPlugin { opts: [Array] } ]');
+        expect(stdout).toContain('plugins: [ WebpackCLITestPlugin { opts: [Array], showAll: true } ]');
     });
 });
diff --git a/test/utils/test-utils.js b/test/utils/test-utils.js
index 8d96d872333..032f15de886 100644
--- a/test/utils/test-utils.js
+++ b/test/utils/test-utils.js
@@ -5,9 +5,11 @@ const execa = require('execa');
 const { sync: spawnSync, node: execaNode } = execa;
 const { Writable } = require('readable-stream');
 const concat = require('concat-stream');
+const { version } = require('webpack');
 
 const WEBPACK_PATH = path.resolve(__dirname, '../../packages/webpack-cli/bin/cli.js');
 const ENABLE_LOG_COMPILATION = process.env.ENABLE_PIPE || false;
+const isWebpack5 = version.startsWith('5');
 
 /**
  * Run the webpack CLI for a test case.
@@ -275,4 +277,5 @@ module.exports = {
     runInstall,
     runInfo,
     hyphenToUpperCase,
+    isWebpack5,
 };
diff --git a/test/utils/webpack-cli-test-plugin.js b/test/utils/webpack-cli-test-plugin.js
index f1bd89b8827..b04869a16e4 100644
--- a/test/utils/webpack-cli-test-plugin.js
+++ b/test/utils/webpack-cli-test-plugin.js
@@ -1,11 +1,14 @@
 class WebpackCLITestPlugin {
-    constructor(options) {
+    constructor(options, showAll = true) {
         this.opts = options;
+        this.showAll = showAll;
     }
 
     apply(compiler) {
         compiler.hooks.done.tap('webpack-cli Test Plugin', () => {
-            console.log(compiler.options);
+            if (this.showAll) {
+                console.log(compiler.options);
+            }
             if (this.opts) {
                 this.opts.map((e) => {
                     const config = Object.getOwnPropertyDescriptor(compiler.options, e);
diff --git a/test/zero-config/entry-present/zero-config.test.js b/test/zero-config/entry-present/zero-config.test.js
index 556db6c6b49..029c385cac3 100644
--- a/test/zero-config/entry-present/zero-config.test.js
+++ b/test/zero-config/entry-present/zero-config.test.js
@@ -8,7 +8,7 @@ describe('Zero Config tests', () => {
         // Should be able to find the entry file
         expect(stdout).toContain('./src/index.js');
         // Should output at the default output dir and filename
-        expect(stdout).toContain('Entrypoint main = main.js');
+        expect(stdout).toContain('main.js');
         // check that the output file exists
         expect(fs.existsSync(path.join(__dirname, '/dist/main.js'))).toBeTruthy();
         expect(stderr).toBeFalsy();