diff --git a/packages/webpack-cli/lib/plugins/WebpackCLIPlugin.js b/packages/webpack-cli/lib/plugins/WebpackCLIPlugin.js
new file mode 100644
index 00000000000..c79c8654a95
--- /dev/null
+++ b/packages/webpack-cli/lib/plugins/WebpackCLIPlugin.js
@@ -0,0 +1,53 @@
+const { packageExists } = require('../utils/package-exists');
+const webpack = packageExists('webpack') ? require('webpack') : undefined;
+const logger = require('../utils/logger');
+
+const PluginName = 'webpack-cli';
+
+class WebpackCLIPlugin {
+    constructor(options) {
+        this.options = options;
+    }
+    async apply(compiler) {
+        const compilers = compiler.compilers || [compiler];
+
+        for (const compiler of compilers) {
+            if (this.options.progress) {
+                const { ProgressPlugin } = compiler.webpack || webpack;
+
+                let progressPluginExists;
+
+                if (compiler.options.plugins) {
+                    progressPluginExists = Boolean(compiler.options.plugins.find((e) => e instanceof ProgressPlugin));
+                }
+
+                if (!progressPluginExists) {
+                    new ProgressPlugin().apply(compiler);
+                }
+            }
+        }
+
+        const compilationName = (compilation) => (compilation.name ? ` ${compilation.name}` : '');
+
+        compiler.hooks.watchRun.tap(PluginName, (compilation) => {
+            const { bail, watch } = compilation.options;
+            if (bail && watch) {
+                logger.warn('You are using "bail" with "watch". "bail" will still exit webpack when the first error is found.');
+            }
+
+            logger.success(`Compilation${compilationName(compilation)} starting...`);
+        });
+
+        compiler.hooks.done.tap(PluginName, (compilation) => {
+            logger.success(`Compilation${compilationName(compilation)} finished`);
+
+            process.nextTick(() => {
+                if (compiler.watchMode) {
+                    logger.success('watching files for updates...');
+                }
+            });
+        });
+    }
+}
+
+module.exports = WebpackCLIPlugin;
diff --git a/packages/webpack-cli/lib/webpack-cli.js b/packages/webpack-cli/lib/webpack-cli.js
index 07bdf950c40..9ae5c1ae010 100644
--- a/packages/webpack-cli/lib/webpack-cli.js
+++ b/packages/webpack-cli/lib/webpack-cli.js
@@ -10,6 +10,7 @@ const { toKebabCase } = require('./utils/helpers');
 const assignFlagDefaults = require('./utils/flag-defaults');
 const { writeFileSync } = require('fs');
 const { options: coloretteOptions } = require('colorette');
+const WebpackCLIPlugin = require('./plugins/WebpackCLIPlugin');
 
 // CLI arg resolvers
 const handleConfigResolution = require('./groups/ConfigGroup');
@@ -212,24 +213,27 @@ class WebpackCLI extends GroupHelper {
         return this.runOptionGroups(args);
     }
 
-    createCompiler(options) {
+    handleError(error) {
+        // https://github.com/webpack/webpack/blob/master/lib/index.js#L267
+        // https://github.com/webpack/webpack/blob/v4.44.2/lib/webpack.js#L90
+        const ValidationError = webpack.ValidationError || webpack.WebpackOptionsValidationError;
+
+        // In case of schema errors print and exit process
+        // For webpack@4 and webpack@5
+        if (error instanceof ValidationError) {
+            logger.error(error.message);
+        } else {
+            logger.error(error);
+        }
+    }
+
+    createCompiler(options, callback) {
         let compiler;
 
         try {
-            compiler = webpack(options);
+            compiler = webpack(options, callback);
         } catch (error) {
-            // https://github.com/webpack/webpack/blob/master/lib/index.js#L267
-            // https://github.com/webpack/webpack/blob/v4.44.2/lib/webpack.js#L90
-            const ValidationError = webpack.ValidationError ? webpack.ValidationError : webpack.WebpackOptionsValidationError;
-
-            // In case of schema errors print and exit process
-            // For webpack@4 and webpack@5
-            if (error instanceof ValidationError) {
-                logger.error(error.message);
-            } else {
-                logger.error(error);
-            }
-
+            this.handleError(error);
             process.exit(2);
         }
 
@@ -245,54 +249,35 @@ class WebpackCLI extends GroupHelper {
     async run(args, cliOptions) {
         await this.processArgs(args, cliOptions);
 
-        const compiler = this.createCompiler(this.compilerConfiguration);
-
-        const options = this.compilerConfiguration;
-        const outputOptions = this.outputConfiguration;
-
-        if (outputOptions.interactive) {
-            const interactive = require('./utils/interactive');
+        let compiler;
 
-            return interactive(compiler, options, outputOptions);
-        }
+        let options = this.compilerConfiguration;
+        let outputOptions = this.outputConfiguration;
 
-        const compilers = compiler.compilers ? compiler.compilers : [compiler];
-        const isWatchMode = Boolean(compilers.find((compiler) => compiler.options.watch));
         const isRawOutput = typeof outputOptions.json === 'undefined';
 
         if (isRawOutput) {
-            for (const compiler of compilers) {
-                if (outputOptions.progress) {
-                    const { ProgressPlugin } = webpack;
-
-                    let progressPluginExists;
-
-                    if (compiler.options.plugins) {
-                        progressPluginExists = Boolean(compiler.options.plugins.find((e) => e instanceof ProgressPlugin));
-                    }
+            const webpackCLIPlugin = new WebpackCLIPlugin({
+                progress: outputOptions.progress,
+            });
 
-                    if (!progressPluginExists) {
-                        new ProgressPlugin().apply(compiler);
-                    }
+            const addPlugin = (options) => {
+                if (!options.plugins) {
+                    options.plugins = [];
                 }
+                options.plugins.unshift(webpackCLIPlugin);
+            };
+            if (Array.isArray(options)) {
+                options.forEach(addPlugin);
+            } else {
+                addPlugin(options);
             }
-
-            compiler.hooks.watchRun.tap('watchInfo', (compilation) => {
-                if (compilation.options.bail && isWatchMode) {
-                    logger.warn('You are using "bail" with "watch". "bail" will still exit webpack when the first error is found.');
-                }
-
-                logger.success(`Compilation${compilation.name ? `${compilation.name}` : ''} starting...`);
-            });
-            compiler.hooks.done.tap('watchInfo', (compilation) => {
-                logger.success(`Compilation${compilation.name ? `${compilation.name}` : ''} finished`);
-            });
         }
 
         const callback = (error, stats) => {
             if (error) {
-                logger.error(error);
-                process.exit(1);
+                this.handleError(error);
+                process.exit(2);
             }
 
             if (stats.hasErrors()) {
@@ -314,9 +299,11 @@ class WebpackCLI extends GroupHelper {
                 return stats;
             };
 
+            const getStatsOptionsFromCompiler = (compiler) => getStatsOptions(compiler.options ? compiler.options.stats : undefined);
+
             const foundStats = compiler.compilers
-                ? { children: compiler.compilers.map((compiler) => getStatsOptions(compiler.options.stats)) }
-                : getStatsOptions(compiler.options.stats);
+                ? { children: compiler.compilers.map(getStatsOptionsFromCompiler) }
+                : getStatsOptionsFromCompiler(compiler);
 
             if (outputOptions.json === true) {
                 process.stdout.write(JSON.stringify(stats.toJson(foundStats), null, 2) + '\n');
@@ -335,46 +322,17 @@ class WebpackCLI extends GroupHelper {
             } else {
                 logger.raw(`${stats.toString(foundStats)}`);
             }
-
-            if (isWatchMode) {
-                logger.success('watching files for updates...');
-            }
         };
 
-        if (isWatchMode) {
-            const watchOptions = (compiler.options && compiler.options.watchOptions) || {};
+        compiler = this.createCompiler(options, callback);
 
-            if (watchOptions.stdin) {
-                process.stdin.on('end', function () {
-                    process.exit();
-                });
-                process.stdin.resume();
-            }
-
-            return new Promise((resolve) => {
-                compiler.watch(watchOptions, (error, stats) => {
-                    callback(error, stats);
+        if (compiler && outputOptions.interactive) {
+            const interactive = require('./utils/interactive');
 
-                    resolve();
-                });
-            });
-        } else {
-            return new Promise((resolve) => {
-                compiler.run((error, stats) => {
-                    if (compiler.close) {
-                        compiler.close(() => {
-                            callback(error, stats);
-
-                            resolve();
-                        });
-                    } else {
-                        callback(error, stats);
-
-                        resolve();
-                    }
-                });
-            });
+            interactive(compiler, options, outputOptions);
         }
+
+        return Promise.resolve();
     }
 }
 
diff --git a/test/core-flags/cache-flags.test.js b/test/core-flags/cache-flags.test.js
index 8a2cb8ccbb8..57a1f0338ac 100644
--- a/test/core-flags/cache-flags.test.js
+++ b/test/core-flags/cache-flags.test.js
@@ -1,10 +1,18 @@
 'use strict';
 
+const path = require('path');
+const rimraf = require('rimraf');
 const { run, isWindows } = require('../utils/test-utils');
 const { existsSync, writeFileSync, unlinkSync } = require('fs');
 const { resolve } = require('path');
 
 describe('cache related flags from core', () => {
+    beforeEach((done) => {
+        rimraf(path.join(__dirname, '../../node_modules/.cache/webpack/*'), () => {
+            done();
+        });
+    });
+
     it('should be successful with --cache ', () => {
         const { stderr, stdout } = run(__dirname, ['--cache']);
         expect(stderr).toBeFalsy();
diff --git a/test/utils/cli-plugin-test/plugin.test.js b/test/utils/cli-plugin-test/plugin.test.js
index 96a5ff20c27..14e4810a3fa 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], showAll: true } ]');
+        expect(stdout).toContain(`  WebpackCLITestPlugin { opts: [Array], showAll: true }`);
     });
 });