diff --git a/packages/webpack-cli/lib/utils/cli-flags.js b/packages/webpack-cli/lib/utils/cli-flags.js
index 7a3476a64a3..8f3256aebb9 100644
--- a/packages/webpack-cli/lib/utils/cli-flags.js
+++ b/packages/webpack-cli/lib/utils/cli-flags.js
@@ -23,7 +23,6 @@ const builtInFlags = [
     // For configs
     {
         name: 'config',
-        usage: '--config <path-to-config> | --config <path-to-config> --config <path-to-config>',
         alias: 'c',
         type: String,
         multiple: true,
@@ -31,14 +30,12 @@ const builtInFlags = [
     },
     {
         name: 'config-name',
-        usage: '--config-name <name-of-config> | --config-name <name-of-config> --config-name <name-of-config>',
         type: String,
         multiple: true,
         description: 'Name of the configuration to use.',
     },
     {
         name: 'merge',
-        usage: '--config <first-config> --config <second-config> --merge',
         alias: 'm',
         type: Boolean,
         description: "Merge two or more configurations using 'webpack-merge'.",
@@ -46,7 +43,6 @@ const builtInFlags = [
     // Complex configs
     {
         name: 'env',
-        usage: '--env <variable> | --env <variable> --env <variable=value>',
         type: (value, previous = {}) => {
             // This ensures we're only splitting by the first `=`
             const [allKeys, val] = value.split(/=(.+)/, 2);
@@ -79,7 +75,6 @@ const builtInFlags = [
     // Adding more plugins
     {
         name: 'hot',
-        usage: '--hot',
         alias: 'h',
         type: Boolean,
         negative: true,
@@ -88,20 +83,17 @@ const builtInFlags = [
     },
     {
         name: 'analyze',
-        usage: '--analyze',
         type: Boolean,
         multiple: false,
         description: 'It invokes webpack-bundle-analyzer plugin to get bundle information.',
     },
     {
         name: 'progress',
-        usage: '--progress | --progress profile',
         type: [Boolean, String],
         description: 'Print compilation progress during build.',
     },
     {
         name: 'prefetch',
-        usage: '--prefetch <request>',
         type: String,
         description: 'Prefetch this request.',
     },
@@ -109,7 +101,6 @@ const builtInFlags = [
     // Output options
     {
         name: 'json',
-        usage: '--json | --json <path-to-stats-file>',
         type: [String, Boolean],
         alias: 'j',
         description: 'Prints result as JSON or store it in a file.',
@@ -118,21 +109,18 @@ const builtInFlags = [
     // For webpack@4
     {
         name: 'entry',
-        usage: '--entry <path-to-entry-file> | --entry <path> --entry <path>',
         type: String,
         multiple: true,
         description: 'The entry point(s) of your application e.g. ./src/main.js.',
     },
     {
         name: 'output-path',
-        usage: '--output-path <path-to-output-directory>',
         alias: 'o',
         type: String,
         description: 'Output location of the file generated by webpack e.g. ./dist/.',
     },
     {
         name: 'target',
-        usage: '--target <value> | --target <value> --target <value>',
         alias: 't',
         type: String,
         multiple: cli !== undefined,
@@ -140,7 +128,6 @@ const builtInFlags = [
     },
     {
         name: 'devtool',
-        usage: '--devtool <value>',
         type: String,
         negative: true,
         alias: 'd',
@@ -149,19 +136,16 @@ const builtInFlags = [
     },
     {
         name: 'mode',
-        usage: '--mode <development | production | none>',
         type: String,
         description: 'Defines the mode to pass to webpack.',
     },
     {
         name: 'name',
-        usage: '--name',
         type: String,
         description: 'Name of the configuration. Used when loading multiple configurations.',
     },
     {
         name: 'stats',
-        usage: '--stats | --stats <value>',
         type: [String, Boolean],
         negative: true,
         description: 'It instructs webpack on how to treat the stats e.g. verbose.',
@@ -169,7 +153,6 @@ const builtInFlags = [
     },
     {
         name: 'watch',
-        usage: '--watch',
         type: Boolean,
         negative: true,
         alias: 'w',
@@ -178,7 +161,6 @@ const builtInFlags = [
     },
     {
         name: 'watch-options-stdin',
-        usage: '--watch-options-stdin',
         type: Boolean,
         negative: true,
         description: 'Stop watching when stdin stream has ended.',
@@ -192,14 +174,11 @@ const coreFlags = cli
     ? Object.entries(cli.getArguments()).map(([flag, meta]) => {
           if (meta.simpleType === 'string') {
               meta.type = String;
-              meta.usage = `--${flag} <value>`;
           } else if (meta.simpleType === 'number') {
               meta.type = Number;
-              meta.usage = `--${flag} <value>`;
           } else {
               meta.type = Boolean;
               meta.negative = !flag.endsWith('-reset');
-              meta.usage = `--${flag}`;
           }
 
           const inBuiltIn = builtInFlags.find((builtInFlag) => builtInFlag.name === flag);
diff --git a/packages/webpack-cli/lib/webpack-cli.js b/packages/webpack-cli/lib/webpack-cli.js
index 3d5a97e8359..1aeaf5504dd 100644
--- a/packages/webpack-cli/lib/webpack-cli.js
+++ b/packages/webpack-cli/lib/webpack-cli.js
@@ -316,7 +316,7 @@ class WebpackCLI {
         const loadCommandByName = async (commandName, allowToInstall = false) => {
             if (commandName === bundleCommandOptions.name || commandName === bundleCommandOptions.alias) {
                 // Make `bundle|b [options]` command
-                this.makeCommand(bundleCommandOptions, this.getBuiltInOptions(), async (program) => {
+                await this.makeCommand(bundleCommandOptions, this.getBuiltInOptions(), async (program) => {
                     const options = program.opts();
 
                     if (program.args.length > 0) {
@@ -430,11 +430,11 @@ class WebpackCLI {
                             process.exit(2);
                         }
 
-                        const found = command.options.find((option) => distance(name, option.long.slice(2)) < 3);
-
-                        if (found) {
-                            logger.error(`Did you mean '--${found.name()}'?`);
-                        }
+                        command.options.forEach((option) => {
+                            if (distance(name, option.long.slice(2)) < 3) {
+                                logger.error(`Did you mean '--${option.name()}'?`);
+                            }
+                        });
                     }
                 }
             }
diff --git a/test/unknown/unknown.test.js b/test/unknown/unknown.test.js
index 78258b22580..8f643d63186 100644
--- a/test/unknown/unknown.test.js
+++ b/test/unknown/unknown.test.js
@@ -144,6 +144,21 @@ describe('unknown behaviour', () => {
         expect(stdout).toBeFalsy();
     });
 
+    it('should log an error if an unknown flag is passed and suggests the closest match to an unknown flag #3', () => {
+        const { exitCode, stderr, stdout } = run(__dirname, ['--output-library-auxiliary-comment-commnjs']);
+
+        expect(exitCode).toBe(2);
+        expect(stderr).toContain("unknown option '--output-library-auxiliary-comment-commnjs'");
+
+        if (isWebpack5) {
+            expect(stderr).toContain("Did you mean '--output-library-auxiliary-comment-commonjs'?");
+            expect(stderr).toContain("Did you mean '--output-library-auxiliary-comment-commonjs2'?");
+        }
+
+        expect(stderr).toContain("Run 'webpack --help' to see available commands and options");
+        expect(stdout).toBeFalsy();
+    });
+
     it('should log an error if an unknown flag is passed and suggests the closest match to an unknown flag using "bundle" command', () => {
         const { exitCode, stderr, stdout } = run(__dirname, ['bundle', '--entyr', './a.js']);