diff --git a/lib/path.js b/lib/path.js
index 6001b0ba8301a7..95cb3201bf2fe0 100644
--- a/lib/path.js
+++ b/lib/path.js
@@ -23,11 +23,15 @@
 
 const {
   FunctionPrototypeBind,
+  RegExp,
   StringPrototypeCharCodeAt,
+  StringPrototypeIndexOf,
   StringPrototypeLastIndexOf,
+  StringPrototypeReplace,
   StringPrototypeSlice,
   StringPrototypeToLowerCase,
 } = primordials;
+
 const {
   CHAR_UPPERCASE_A,
   CHAR_LOWERCASE_A,
@@ -1014,7 +1018,17 @@ const posix = {
     let resolvedAbsolute = false;
 
     for (let i = args.length - 1; i >= -1 && !resolvedAbsolute; i--) {
-      const path = i >= 0 ? args[i] : process.cwd();
+      let path;
+      if (i >= 0) {
+        path = args[i];
+      } else {
+        const _ = StringPrototypeReplace(
+          process.cwd(),
+          new RegExp(`\\${module.exports.sep}`, 'g'),
+          posix.sep
+        );
+        path = StringPrototypeSlice(_, StringPrototypeIndexOf(_, posix.sep));
+      }
 
       validateString(path, 'path');
 
diff --git a/test/known_issues/known_issues.status b/test/known_issues/known_issues.status
index 690e6e9840b77c..7a50c10404c723 100644
--- a/test/known_issues/known_issues.status
+++ b/test/known_issues/known_issues.status
@@ -15,32 +15,18 @@ test-vm-timeout-escape-queuemicrotask: SKIP
 [$system==win32]
 
 [$system==linux]
-# Windows-specific test
-test-path-posix-relative-on-windows: SKIP
 
 [$system==macos]
-# Windows-specific test
-test-path-posix-relative-on-windows: SKIP
 
 [$system==solaris]
-# Windows-specific test
-test-path-posix-relative-on-windows: SKIP
 
 [$system==freebsd]
-# Windows-specific test
-test-path-posix-relative-on-windows: SKIP
 
 [$system==aix]
-# Windows-specific test
-test-path-posix-relative-on-windows: SKIP
 
 [$arch==arm]
 # The Raspberry Pis are too slow to run this test.
 # See https://github.com/nodejs/build/issues/2227#issuecomment-608334574
 test-crypto-authenticated-stream: SKIP
-# Windows-specific test
-test-path-posix-relative-on-windows: SKIP
 
 [$system==ibmi]
-# Windows-specific test
-test-path-posix-relative-on-windows: SKIP
diff --git a/test/known_issues/test-path-posix-relative-on-windows.js b/test/parallel/test-path-posix-relative-on-windows.js
similarity index 100%
rename from test/known_issues/test-path-posix-relative-on-windows.js
rename to test/parallel/test-path-posix-relative-on-windows.js
diff --git a/test/parallel/test-path-resolve.js b/test/parallel/test-path-resolve.js
index 8bf8001ea2f0f2..77eafd543aac18 100644
--- a/test/parallel/test-path-resolve.js
+++ b/test/parallel/test-path-resolve.js
@@ -9,6 +9,14 @@ const failures = [];
 const slashRE = /\//g;
 const backslashRE = /\\/g;
 
+const posixyCwd = common.isWindows ?
+  (() => {
+    const _ = process.cwd()
+      .replaceAll(path.sep, path.posix.sep);
+    return _.slice(_.indexOf(path.posix.sep));
+  })() :
+  process.cwd();
+
 const resolveTests = [
   [ path.win32.resolve,
     // Arguments                               result
@@ -31,8 +39,8 @@ const resolveTests = [
     // Arguments                    result
     [[['/var/lib', '../', 'file/'], '/var/file'],
      [['/var/lib', '/../', 'file/'], '/file'],
-     [['a/b/c/', '../../..'], process.cwd()],
-     [['.'], process.cwd()],
+     [['a/b/c/', '../../..'], posixyCwd],
+     [['.'], posixyCwd],
      [['/some/dir', '.', '/absolute/'], '/absolute'],
      [['/foo/tmp.3/', '../tmp.3/cycles/root.js'], '/foo/tmp.3/cycles/root.js'],
     ],