diff --git a/CHANGELOG.md b/CHANGELOG.md
index 8caaba089165..c8a48c7b9beb 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -17,6 +17,7 @@ None for now
 
 * `[jest-runtime]` fix error for test files providing coverage.
   ([#5117](https://github.com/facebook/jest/pull/5117))
+* `[jest-config]` fix unexpected condition to avoid infinite recursion in Windows platform.([#5161](https://github.com/facebook/jest/pull/5161))
 
 ### Features
 
diff --git a/packages/jest-config/src/__tests__/resolve_config_path.test.js b/packages/jest-config/src/__tests__/resolve_config_path.test.js
index 59f0be86b9ef..e9a60a3a8c52 100644
--- a/packages/jest-config/src/__tests__/resolve_config_path.test.js
+++ b/packages/jest-config/src/__tests__/resolve_config_path.test.js
@@ -11,12 +11,8 @@ import os from 'os';
 import path from 'path';
 import resolveConfigPath from '../resolve_config_path';
 
-import skipOnWindows from '../../../../scripts/skip_on_windows';
-
 const {cleanup, writeFiles} = require('../../../../integration_tests/utils');
 
-skipOnWindows.suite();
-
 const DIR = path.resolve(os.tmpdir(), 'resolve_config_path_test');
 const ERROR_PATTERN = /Could not find a config file based on provided values/;
 const NO_ROOT_DIR_ERROR_PATTERN = /Can\'t find a root directory/;
diff --git a/packages/jest-config/src/resolve_config_path.js b/packages/jest-config/src/resolve_config_path.js
index 9e35582b01db..1494552d44cc 100644
--- a/packages/jest-config/src/resolve_config_path.js
+++ b/packages/jest-config/src/resolve_config_path.js
@@ -66,7 +66,7 @@ const resolveConfigPathByTraversing = (
 
   // This is the system root.
   // We tried everything, config is nowhere to be found ¯\_(ツ)_/¯
-  if (pathToResolve === path.sep) {
+  if (pathToResolve === path.dirname(pathToResolve)) {
     throw new Error(makeResolutionErrorMessage(initialPath, cwd));
   }