diff --git a/packages/webpack-cli/lib/groups/HelpGroup.js b/packages/webpack-cli/lib/groups/HelpGroup.js
index 5e21c3e9ab8..006b1cdebf0 100644
--- a/packages/webpack-cli/lib/groups/HelpGroup.js
+++ b/packages/webpack-cli/lib/groups/HelpGroup.js
@@ -21,10 +21,10 @@ class HelpGroup {
             const link = options.link;
 
             process.stdout.write(`${header('Usage')}: ${usage}\n`);
-            process.stdout.write(`${header('Description')}: ${description}\n`);
+            process.stdout.write(`\n${header('Description')}: ${description}\n`);
 
             if (link) {
-                process.stdout.write(`${header('Documentation')}: ${link}\n`);
+                process.stdout.write(`\n${header('Documentation')}: ${link}\n`);
             }
 
             if (options.flags) {
@@ -103,12 +103,16 @@ class HelpGroup {
             {
                 header: 'Available Commands',
                 content: options.commands.map((e) => {
-                    return { name: e.name, summary: e.description };
+                    return { name: e.name, summary: e.shortDesc ? e.shortDesc : e.description };
                 }),
             },
             {
                 header: 'Options',
-                optionList: options.core,
+                optionList: options.core.map((e) => {
+                    const description = e.shortDesc ? e.shortDesc : e.description;
+                    e.description = description;
+                    return e;
+                }),
             },
         ]);
         return {
diff --git a/packages/webpack-cli/lib/utils/cli-flags.js b/packages/webpack-cli/lib/utils/cli-flags.js
index 657897e5a08..289e0d60877 100644
--- a/packages/webpack-cli/lib/utils/cli-flags.js
+++ b/packages/webpack-cli/lib/utils/cli-flags.js
@@ -1,3 +1,5 @@
+const StatsGroup = require('../groups/StatsGroup');
+
 const HELP_GROUP = 'help';
 const CONFIG_GROUP = 'config';
 const BASIC_GROUP = 'basic';
@@ -6,6 +8,13 @@ const ADVANCED_GROUP = 'advanced';
 const DISPLAY_GROUP = 'stats';
 const ZERO_CONFIG_GROUP = 'zero-config';
 
+function acceptedString(arr) {
+    return `Accepted Value: ${arr.join(' | ')}`;
+}
+function descriptionGenerator(example, shortDesc, acceptedValue = []) {
+    return `\n\n    Example: ${example}\n\n     ${acceptedValue.length > 0 ? acceptedString(acceptedValue) : ''}\n\n${shortDesc}`;
+}
+
 module.exports = {
     groups: {
         HELP_GROUP,
@@ -76,7 +85,11 @@ module.exports = {
             type: String,
             defaultOption: true,
             group: BASIC_GROUP,
-            description: 'The entry point of your application.',
+            shortDesc: 'The entry point of your application.',
+            description: descriptionGenerator(
+                'webpack --entry index.js',
+                'It is the entry point of your application. You can provide multiple entry points also.',
+            ),
             link: 'https://webpack.js.org/concepts/#entry',
         },
         {
@@ -86,7 +99,11 @@ module.exports = {
             type: String,
             defaultValue: null,
             group: CONFIG_GROUP,
-            description: 'Provide path to a webpack configuration file',
+            shortDesc: 'Provide path to a webpack configuration file',
+            description: descriptionGenerator(
+                'webpack-cli --config ./webpack.config.js',
+                'It provides path to a webpack configuration file',
+            ),
             link: 'https://webpack.js.org/configuration/',
         },
         {
@@ -133,15 +150,17 @@ module.exports = {
             alias: 'o',
             group: OUTPUT_GROUP,
             type: String,
-            description: 'Output location of the file generated by webpack',
+            shortDesc: 'Output location of the file generated by webpack',
+            description: descriptionGenerator('webpack --output ./a.js', 'Output location to the file generated by webpack'),
             link: 'https://webpack.js.org/concepts/#output',
         },
         {
             name: 'plugin',
-            usage: '--plugin',
+            usage: '--plugin <plugin name> e.g. HtmlWebpackPlugin',
             group: ADVANCED_GROUP,
             type: String,
-            description: 'Load a given plugin',
+            shortDesc: 'Load a given plugin',
+            description: descriptionGenerator('webpack --plugin ExtractTextWebpackPlugin', 'Load a plugin '),
             link: 'https://webpack.js.org/plugins/',
         },
         {
@@ -150,7 +169,17 @@ module.exports = {
             alias: 't',
             type: String,
             group: ADVANCED_GROUP,
-            description: 'Sets the build target',
+            shortDesc: 'Sets the build target',
+            description: descriptionGenerator('webpack --target node ', 'Instructs webpack to target a specific environment.', [
+                'async-node',
+                'electron-main',
+                'electron-renderer',
+                'electron-preload',
+                'node',
+                'node-webkit',
+                'web',
+                'webworker',
+            ]),
             link: 'https://webpack.js.org/configuration/target/#target',
         },
         {
@@ -247,7 +276,12 @@ module.exports = {
             type: String,
             defaultValue: 'normal',
             group: DISPLAY_GROUP,
-            description: 'It instructs webpack on how to treat the stats',
+            shortDesc: 'It instructs webpack on how to treat the stats',
+            description: descriptionGenerator(
+                'npx webpack-cli --stats verbose',
+                'These options instructs webpack on how to treat the stats.',
+                StatsGroup.validOptions(),
+            ),
             link: 'https://webpack.js.org/configuration/stats/#stats',
         },
         {
diff --git a/test/help/help-flags.test.js b/test/help/help-flags.test.js
index 76e0bc05e56..f8d493cd804 100644
--- a/test/help/help-flags.test.js
+++ b/test/help/help-flags.test.js
@@ -2,6 +2,7 @@
 
 const { run } = require('../utils/test-utils');
 const helpHeader = 'The build tool for modern web applications';
+const footer = 'Made with ♥️  by the webpack team';
 
 describe('commands help', () => {
     it('throws error for invalid flag with --help flag', () => {
@@ -27,4 +28,10 @@ describe('commands help', () => {
         expect(stdout).toContain('webpack --entry <path to entry file> e.g. ./src/main.js');
         expect(stderr).toHaveLength(0);
     });
+    it('shows accepted value if available for a flag', () => {
+        const { stdout, stderr } = run(__dirname, ['--help', '--stats'], false);
+        expect(stdout).toContain(footer);
+        expect(stdout).toContain('Accepted Value: none | errors-only | minimal | normal | detailed | verbose | errors-warnings');
+        expect(stderr).toHaveLength(0);
+    });
 });