diff --git a/packages/webpack-cli/lib/groups/BasicGroup.js b/packages/webpack-cli/lib/groups/BasicGroup.js
index de43289985e..cbf8a41806d 100644
--- a/packages/webpack-cli/lib/groups/BasicGroup.js
+++ b/packages/webpack-cli/lib/groups/BasicGroup.js
@@ -36,6 +36,9 @@ class BasicGroup extends GroupHelper {
             if (arg === 'name') {
                 options.name = args[arg];
             }
+            if (arg === 'watch') {
+                options.watch = true;
+            }
             if (arg === 'entry') {
                 options[arg] = this.resolveFilePath(args[arg], 'index.js');
                 if (options[arg].length === 0) {
diff --git a/packages/webpack-cli/lib/utils/Compiler.js b/packages/webpack-cli/lib/utils/Compiler.js
index 20774ddbe9e..7b34f078b28 100644
--- a/packages/webpack-cli/lib/utils/Compiler.js
+++ b/packages/webpack-cli/lib/utils/Compiler.js
@@ -1,5 +1,6 @@
 const webpack = require('webpack');
 const logger = require('./logger');
+const bailAndWatchWarning = require('./warnings/bailAndWatchWarning');
 const { CompilerOutput } = require('./CompilerOutput');
 
 class Compiler {
@@ -119,9 +120,11 @@ class Compiler {
 
         if (this.compiler.compilers) {
             this.compiler.compilers.forEach((comp, idx) => {
+                bailAndWatchWarning(comp); //warn the user if bail and watch both are used together
                 this.setUpHookForCompilation(comp, outputOptions, options[idx]);
             });
         } else {
+            bailAndWatchWarning(this.compiler);
             this.setUpHookForCompilation(this.compiler, outputOptions, options);
         }
 
diff --git a/packages/webpack-cli/lib/utils/warnings/bailAndWatchWarning.js b/packages/webpack-cli/lib/utils/warnings/bailAndWatchWarning.js
new file mode 100644
index 00000000000..84894469cab
--- /dev/null
+++ b/packages/webpack-cli/lib/utils/warnings/bailAndWatchWarning.js
@@ -0,0 +1,14 @@
+const logger = require('../logger');
+
+/**
+ * warn the user if bail and watch both are used together
+ * @param {Object} webpack compiler
+ * @returns {void}
+ */
+const bailAndWatchWarning = (compiler) => {
+    if (compiler.options.bail && compiler.options.watch) {
+        logger.warn('You are using "bail" with "watch". "bail" will still exit webpack when the first error is found.');
+    }
+};
+
+module.exports = bailAndWatchWarning;
diff --git a/test/bail/bail-and-watch-warning.test.js b/test/bail/bail-and-watch-warning.test.js
new file mode 100644
index 00000000000..088d8717967
--- /dev/null
+++ b/test/bail/bail-and-watch-warning.test.js
@@ -0,0 +1,26 @@
+'use strict';
+
+const { run } = require('../utils/test-utils');
+
+describe('bail and watch warning', () => {
+    it('should log warning in case of single compiler', () => {
+        const { stderr, stdout } = run(__dirname, ['-c', 'single-webpack.config.js']);
+
+        expect(stderr).toContain(`You are using "bail" with "watch". "bail" will still exit webpack when the first error is found.`);
+        expect(stdout).toBeTruthy();
+    });
+
+    it('should log warning in case of multiple compilers', () => {
+        const { stderr, stdout } = run(__dirname, ['-c', 'multi-webpack.config.js']);
+
+        expect(stderr).toContain(`You are using "bail" with "watch". "bail" will still exit webpack when the first error is found.`);
+        expect(stdout).toBeTruthy();
+    });
+
+    it('should log not log warning if both are not true', () => {
+        const { stderr, stdout } = run(__dirname, ['-c', 'third-webpack.config.js']);
+
+        expect(stderr).not.toContain(`You are using "bail" with "watch". "bail" will still exit webpack when the first error is found.`);
+        expect(stdout).toBeTruthy();
+    });
+});
diff --git a/test/bail/multi-webpack.config.js b/test/bail/multi-webpack.config.js
new file mode 100644
index 00000000000..497c9ff6162
--- /dev/null
+++ b/test/bail/multi-webpack.config.js
@@ -0,0 +1,20 @@
+module.exports = [
+    {
+        output: {
+            filename: './dist-first.js',
+        },
+        name: 'first',
+        entry: './src/first.js',
+        mode: 'development',
+    },
+    {
+        output: {
+            filename: './dist-second.js',
+        },
+        name: 'second',
+        entry: './src/second.js',
+        mode: 'production',
+        bail: true,
+        watch: true,
+    },
+];
diff --git a/test/bail/single-webpack.config.js b/test/bail/single-webpack.config.js
new file mode 100644
index 00000000000..132930c4f13
--- /dev/null
+++ b/test/bail/single-webpack.config.js
@@ -0,0 +1,6 @@
+module.exports = {
+    entry: './src/first.js',
+    mode: 'development',
+    bail: true,
+    watch: true,
+};
diff --git a/test/bail/src/first.js b/test/bail/src/first.js
new file mode 100644
index 00000000000..fb7e56835c4
--- /dev/null
+++ b/test/bail/src/first.js
@@ -0,0 +1 @@
+console.log('bail and watch warning test first');
diff --git a/test/bail/src/second.js b/test/bail/src/second.js
new file mode 100644
index 00000000000..5b277372189
--- /dev/null
+++ b/test/bail/src/second.js
@@ -0,0 +1 @@
+console.log('bail and watch warning test second');
diff --git a/test/bail/third-webpack.config.js b/test/bail/third-webpack.config.js
new file mode 100644
index 00000000000..b0b7ac2f33c
--- /dev/null
+++ b/test/bail/third-webpack.config.js
@@ -0,0 +1,5 @@
+module.exports = {
+    entry: './src/first.js',
+    mode: 'development',
+    bail: true,
+};