diff --git a/packages/webpack-cli/__tests__/arg-parser.test.js b/packages/webpack-cli/__tests__/arg-parser.test.js
index dca85eb4031..a2712c7edf4 100644
--- a/packages/webpack-cli/__tests__/arg-parser.test.js
+++ b/packages/webpack-cli/__tests__/arg-parser.test.js
@@ -368,7 +368,7 @@ describe('arg-parser', () => {
         expect(res.unknownArgs.length).toEqual(0);
         expect(res.opts.entry).toEqual(['test.js']);
         expect(res.opts.hot).toBeTruthy();
-        expect(res.opts.output).toEqual('./dist/');
+        expect(res.opts.outputPath).toEqual('./dist/');
         expect(res.opts.stats).toEqual(true);
         expect(warnMock.mock.calls.length).toEqual(0);
     });
diff --git a/packages/webpack-cli/__tests__/resolveOutput.test.js b/packages/webpack-cli/__tests__/resolveOutput.test.js
index 1031f8d7e8f..3522d5b1068 100644
--- a/packages/webpack-cli/__tests__/resolveOutput.test.js
+++ b/packages/webpack-cli/__tests__/resolveOutput.test.js
@@ -1,10 +1,11 @@
+const { resolve } = require('path');
 const resolveOutput = require('../lib/groups/resolveOutput');
 
 describe('OutputGroup', function () {
     it('should handle the output option', () => {
         const result = resolveOutput({
-            output: './bundle.js',
+            outputPath: './bundle',
         });
-        expect(result.options.output.filename).toEqual('bundle.js');
+        expect(result.options.output.path).toEqual(resolve('bundle'));
     });
 });
diff --git a/packages/webpack-cli/lib/groups/resolveOutput.js b/packages/webpack-cli/lib/groups/resolveOutput.js
index c8fd64aaf35..b658a9e8a55 100644
--- a/packages/webpack-cli/lib/groups/resolveOutput.js
+++ b/packages/webpack-cli/lib/groups/resolveOutput.js
@@ -5,15 +5,13 @@ const path = require('path');
  * @param {args} args - Parsed arguments passed to the CLI
  */
 const resolveOutput = (args) => {
-    const { output } = args;
+    const { outputPath } = args;
     const finalOptions = {
         options: { output: {} },
         outputOptions: {},
     };
-    if (output) {
-        const { dir, base, ext } = path.parse(output);
-        finalOptions.options.output.path = ext.length === 0 ? path.resolve(dir, base) : path.resolve(dir);
-        if (ext.length > 0) finalOptions.options.output.filename = base;
+    if (outputPath) {
+        finalOptions.options.output.path = path.resolve(outputPath);
     }
     return finalOptions;
 };
diff --git a/packages/webpack-cli/lib/utils/cli-flags.js b/packages/webpack-cli/lib/utils/cli-flags.js
index 2a274b08b88..fbdfc993534 100644
--- a/packages/webpack-cli/lib/utils/cli-flags.js
+++ b/packages/webpack-cli/lib/utils/cli-flags.js
@@ -117,8 +117,8 @@ const core = [
         description: 'Outputs list of supported flags',
     },
     {
-        name: 'output',
-        usage: '--output <path to output directory>',
+        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/',
diff --git a/test/config/basic/basic-config.test.js b/test/config/basic/basic-config.test.js
index 01feb8afb94..a2d876db072 100644
--- a/test/config/basic/basic-config.test.js
+++ b/test/config/basic/basic-config.test.js
@@ -1,21 +1,13 @@
 'use strict';
-const { stat } = require('fs');
+const { existsSync } = require('fs');
 const { resolve } = require('path');
 const { run } = require('../../utils/test-utils');
 
 describe('basic config file', () => {
-    it('is able to understand and parse a very basic configuration file', (done) => {
-        const { stdout, stderr } = run(
-            __dirname,
-            ['-c', resolve(__dirname, 'webpack.config.js'), '--output', './binary/a.bundle.js'],
-            false,
-        );
+    it('is able to understand and parse a very basic configuration file', () => {
+        const { stdout, stderr } = run(__dirname, ['-c', resolve(__dirname, 'webpack.config.js'), '--output-path', './binary'], false);
         expect(stderr).toBeFalsy();
-        expect(stdout).not.toBe(undefined);
-        stat(resolve(__dirname, './binary/a.bundle.js'), (err, stats) => {
-            expect(err).toBe(null);
-            expect(stats.isFile()).toBe(true);
-            done();
-        });
+        expect(stdout).toBeTruthy();
+        expect(existsSync(resolve(__dirname, './binary/a.bundle.js'))).toBeTruthy();
     });
 });
diff --git a/test/defaults/output-defaults.test.js b/test/defaults/output-defaults.test.js
index 11079b0f90e..18cd26d8e17 100644
--- a/test/defaults/output-defaults.test.js
+++ b/test/defaults/output-defaults.test.js
@@ -5,7 +5,7 @@ const { run } = require('../utils/test-utils');
 
 describe('output flag defaults', () => {
     it('should create default file for a given directory', (done) => {
-        const { stdout } = run(__dirname, ['--entry', './a.js', '--output', './binary'], false);
+        const { stdout } = run(__dirname, ['--entry', './a.js', '--output-path', './binary'], false);
         // Should not print warning about config fallback, as we have production as default
         expect(stdout).not.toContain('option has not been set, webpack will fallback to');
         stat(resolve(__dirname, './binary/main.js'), (err, stats) => {
@@ -26,7 +26,7 @@ describe('output flag defaults', () => {
     });
 
     it('throw error on empty output flag', () => {
-        const { stderr } = run(__dirname, ['--entry', './a.js', '--output'], false);
-        expect(stderr).toContain("error: option '-o, --output <value>' argument missing");
+        const { stderr } = run(__dirname, ['--entry', './a.js', '--output-path'], false);
+        expect(stderr).toContain("error: option '-o, --output-path <value>' argument missing");
     });
 });
diff --git a/test/devtool/array/source-map-array.test.js b/test/devtool/array/source-map-array.test.js
index 9bedc1e4e8a..3672c8eaba7 100644
--- a/test/devtool/array/source-map-array.test.js
+++ b/test/devtool/array/source-map-array.test.js
@@ -14,7 +14,7 @@ describe('source-map object', () => {
         });
     });
     it('should override entire array on flag', (done) => {
-        const { stderr } = run(__dirname, ['--devtool', 'source-map', '--output', './binary'], false);
+        const { stderr } = run(__dirname, ['--devtool', 'source-map', '--output-path', './binary'], false);
         expect(stderr).toBe('');
         readdir(resolve(__dirname, 'binary'), (err, files) => {
             expect(err).toBe(null);
diff --git a/test/devtool/object/source-map-object.test.js b/test/devtool/object/source-map-object.test.js
index c537cbd65e1..9418f2eaa2e 100644
--- a/test/devtool/object/source-map-object.test.js
+++ b/test/devtool/object/source-map-object.test.js
@@ -24,7 +24,7 @@ describe('source-map object', () => {
     });
 
     it('should override config with source-map', (done) => {
-        run(__dirname, ['-c', './webpack.eval.config.js', '--devtool', 'source-map', '-o', './binary/dist-amd.js'], false);
+        run(__dirname, ['-c', './webpack.eval.config.js', '--devtool', 'source-map', '-o', './binary'], false);
         stat(resolve(__dirname, 'binary/dist-amd.js.map'), (err, stats) => {
             expect(err).toBe(null);
             expect(stats.isFile()).toBe(true);
diff --git a/test/entry/defaults-index/entry-multi-args.test.js b/test/entry/defaults-index/entry-multi-args.test.js
index 270e0f8a94d..6ce53ebc2eb 100644
--- a/test/entry/defaults-index/entry-multi-args.test.js
+++ b/test/entry/defaults-index/entry-multi-args.test.js
@@ -18,7 +18,7 @@ describe('single entry flag index present', () => {
     });
 
     it('finds default index file, compiles and overrides with flags successfully', (done) => {
-        const { stderr } = run(__dirname, ['--output', 'bin/main.js']);
+        const { stderr } = run(__dirname, ['--output-path', 'bin']);
         expect(stderr).toBeFalsy();
 
         stat(resolve(__dirname, './bin/main.js'), (err, stats) => {
diff --git a/test/node/node.test.js b/test/node/node.test.js
index 63114299a8e..d922b3fb61b 100644
--- a/test/node/node.test.js
+++ b/test/node/node.test.js
@@ -8,7 +8,7 @@ const { run } = require('../utils/test-utils');
 // throws different error from what we manually see
 describe('node flags', () => {
     it('is able to pass the options flags to node js', async (done) => {
-        const { stdout, stderr } = await run(__dirname, ['--output', './bin/[name].bundle.js'], false, [
+        const { stdout, stderr } = await run(__dirname, ['--output-path', './bin'], false, [
             `--require=${resolve(__dirname, 'bootstrap.js')}`,
             `--require=${resolve(__dirname, 'bootstrap2.js')}`,
         ]);
diff --git a/test/node/webpack.config.js b/test/node/webpack.config.js
index b58f8a91f0d..4913dff71b6 100644
--- a/test/node/webpack.config.js
+++ b/test/node/webpack.config.js
@@ -4,6 +4,6 @@ module.exports = {
     entry: './a.js',
     output: {
         path: resolve(__dirname, 'binary'),
-        filename: 'a.bundle.js',
+        filename: '[name].bundle.js',
     },
 };
diff --git a/test/output/named-bundles/output-named-bundles.test.js b/test/output/named-bundles/output-named-bundles.test.js
index 612fb8ae105..ecd7970531f 100644
--- a/test/output/named-bundles/output-named-bundles.test.js
+++ b/test/output/named-bundles/output-named-bundles.test.js
@@ -5,7 +5,7 @@ const { run } = require('../../utils/test-utils');
 
 describe('output flag named bundles', () => {
     it('should output file given as flag instead of in configuration', () => {
-        const { stderr } = run(__dirname, ['-c', resolve(__dirname, 'webpack.config.js'), '--output', './binary/a.bundle.js'], false);
+        const { stderr } = run(__dirname, ['-c', resolve(__dirname, 'webpack.config.js'), '--output-path', './binary'], false);
         expect(stderr).toBeFalsy();
 
         const stats = statSync(resolve(__dirname, './binary/a.bundle.js'));
@@ -13,7 +13,7 @@ describe('output flag named bundles', () => {
     });
 
     it('should resolve the path to binary/a.bundle.js as ./binary/a.bundle.js', () => {
-        const { stderr } = run(__dirname, ['-c', resolve(__dirname, 'webpack.config.js'), '--output', 'binary/a.bundle.js'], false);
+        const { stderr } = run(__dirname, ['-c', resolve(__dirname, 'webpack.config.js'), '--output-path', 'binary'], false);
         expect(stderr).toBeFalsy();
 
         const stats = statSync(resolve(__dirname, './binary/a.bundle.js'));
@@ -21,11 +21,7 @@ describe('output flag named bundles', () => {
     });
 
     it('should create multiple bundles with an overriding flag', () => {
-        const { stderr } = run(
-            __dirname,
-            ['-c', resolve(__dirname, 'webpack.single.config.js'), '--output', './bin/[name].bundle.js'],
-            false,
-        );
+        const { stderr } = run(__dirname, ['-c', resolve(__dirname, 'webpack.single.config.js'), '--output-path', './bin'], false);
         expect(stderr).toBeFalsy();
 
         let stats = statSync(resolve(__dirname, './bin/b.bundle.js'));
@@ -45,8 +41,8 @@ describe('output flag named bundles', () => {
     });
 
     it('should output file in bin directory using default webpack config with warning for empty output value', () => {
-        const { stdout, stderr, exitCode } = run(__dirname, ['--output'], false);
-        expect(stderr).toEqual("error: option '-o, --output <value>' argument missing");
+        const { stdout, stderr, exitCode } = run(__dirname, ['--output-path'], false);
+        expect(stderr).toEqual("error: option '-o, --output-path <value>' argument missing");
         expect(exitCode).toEqual(1);
         expect(stdout).toBeFalsy();
     });
diff --git a/test/output/named-bundles/webpack.config.js b/test/output/named-bundles/webpack.config.js
index 0029ad8473f..e6d61551f48 100644
--- a/test/output/named-bundles/webpack.config.js
+++ b/test/output/named-bundles/webpack.config.js
@@ -4,6 +4,6 @@ module.exports = {
     entry: './a.js',
     output: {
         path: resolve(__dirname, 'bin'),
-        filename: 'bundle.js',
+        filename: 'a.bundle.js',
     },
 };
diff --git a/test/output/named-bundles/webpack.single.config.js b/test/output/named-bundles/webpack.single.config.js
index 112d94387a1..32f35d14cd0 100644
--- a/test/output/named-bundles/webpack.single.config.js
+++ b/test/output/named-bundles/webpack.single.config.js
@@ -7,6 +7,6 @@ module.exports = {
     },
     output: {
         path: resolve(__dirname, 'bin'),
-        filename: 'bundle.js',
+        filename: '[name].bundle.js',
     },
 };
diff --git a/test/utils/test-utils.js b/test/utils/test-utils.js
index 87ae5ecffb8..4cd27900e9f 100644
--- a/test/utils/test-utils.js
+++ b/test/utils/test-utils.js
@@ -24,7 +24,7 @@ const run = (testCase, args = [], setOutput = true, nodeArgs = [], env) => {
 
     const outputPath = path.resolve(testCase, 'bin');
     const processExecutor = nodeArgs.length ? execaNode : spawnSync;
-    const argsWithOutput = setOutput ? args.concat('--output', outputPath) : args;
+    const argsWithOutput = setOutput ? args.concat('--output-path', outputPath) : args;
     const result = processExecutor(WEBPACK_PATH, argsWithOutput, {
         cwd,
         reject: false,
@@ -40,7 +40,7 @@ const runWatch = ({ testCase, args = [], setOutput = true, outputKillStr = 'Time
     const cwd = path.resolve(testCase);
 
     const outputPath = path.resolve(testCase, 'bin');
-    const argsWithOutput = setOutput ? args.concat('--output', outputPath) : args;
+    const argsWithOutput = setOutput ? args.concat('--output-path', outputPath) : args;
 
     return new Promise((resolve, reject) => {
         const watchPromise = execa(WEBPACK_PATH, argsWithOutput, {
@@ -76,7 +76,7 @@ const runAndGetWatchProc = (testCase, args = [], setOutput = true, input = '', f
     const cwd = path.resolve(testCase);
 
     const outputPath = path.resolve(testCase, 'bin');
-    const argsWithOutput = setOutput ? args.concat('--output', outputPath) : args;
+    const argsWithOutput = setOutput ? args.concat('--output-path', outputPath) : args;
 
     const options = {
         cwd,
diff --git a/test/utils/test-utils.test.js b/test/utils/test-utils.test.js
index a7a6f0d6029..0c8ac2ad1e6 100644
--- a/test/utils/test-utils.test.js
+++ b/test/utils/test-utils.test.js
@@ -38,7 +38,7 @@ describe('run function', () => {
         // Executes the correct command
         expect(command).toContain('cli.js');
         // Should use apply a default output dir
-        expect(command).toContain('--output');
+        expect(command).toContain('--output-path');
         expect(command).toContain('bin');
         expect(stdout).toBeTruthy();
         expect(stderr).toBeFalsy();
@@ -61,7 +61,7 @@ describe('run function', () => {
     it('uses default output when output param is false', () => {
         const { stdout, stderr, command } = run(__dirname, [], false);
         // execution command contains info command
-        expect(command).not.toContain('--output');
+        expect(command).not.toContain('--output-path');
         expect(stdout).toBeTruthy();
         expect(stderr).toBeFalsy();
     });
@@ -73,7 +73,7 @@ describe('runAndGetWatchProc function', () => {
         // Executes the correct command
         expect(command).toContain('cli.js');
         // Should use apply a default output dir
-        expect(command).toContain('--output');
+        expect(command).toContain('--output-path');
         expect(command).toContain('bin');
         expect(stdout).toBeTruthy();
         expect(stderr).toBeFalsy();
@@ -96,7 +96,7 @@ describe('runAndGetWatchProc function', () => {
     it('uses default output when output param is false', async () => {
         const { stdout, stderr, command } = await runAndGetWatchProc(__dirname, [], false);
         // execution command contains info command
-        expect(command).not.toContain('--output');
+        expect(command).not.toContain('--output-path');
         expect(stdout).toBeTruthy();
         expect(stderr).toBeFalsy();
     });