diff --git a/packages/webpack-cli/lib/groups/ConfigGroup.js b/packages/webpack-cli/lib/groups/ConfigGroup.js
index 93920dddaeb..ed22885fce9 100644
--- a/packages/webpack-cli/lib/groups/ConfigGroup.js
+++ b/packages/webpack-cli/lib/groups/ConfigGroup.js
@@ -127,11 +127,6 @@ class ConfigGroup extends GroupHelper {
             newOptionsObject['options'] = configOptions;
         }
 
-        //warn the user if bail and watch both are used together
-        if (configOptions.bail && configOptions.watch) {
-            logger.warn('You are using "bail" with "watch". "bail" will still exit webpack when the first error is found.');
-        }
-
         if (configOptions && configPath.includes('.webpack')) {
             const currentPath = configPath;
             const parentContext = dirname(currentPath).split(sep).slice(0, -1).join(sep);
diff --git a/packages/webpack-cli/lib/utils/Compiler.js b/packages/webpack-cli/lib/utils/Compiler.js
index 4a2c4686e96..02176653d2c 100644
--- a/packages/webpack-cli/lib/utils/Compiler.js
+++ b/packages/webpack-cli/lib/utils/Compiler.js
@@ -118,7 +118,7 @@ class Compiler {
         }
 
         //warn the user if bail and watch both are used together
-        if (this.compiler.options.bail && outputOptions.watch) {
+        if (this.compiler.options.bail && (outputOptions.watch || options.watch)) {
             logger.warn('You are using "bail" with "watch". "bail" will still exit webpack when the first error is found.');
         }