diff --git a/.github/workflows/run-tests.yml b/.github/workflows/run-tests.yml
index b67ff04..8ec5f09 100644
--- a/.github/workflows/run-tests.yml
+++ b/.github/workflows/run-tests.yml
@@ -11,11 +11,15 @@ jobs:
       matrix:
         php: [8.1, 8.0, 7.4]
         dependency-version: [prefer-lowest, prefer-stable]
+        operating-system:
+          - "macos-latest"
+          - "ubuntu-latest"
+          - "windows-latest"
         exclude:
           - php: 8.1
             dependency-version: prefer-lowest
 
-    name: P${{ matrix.php }} - ${{ matrix.dependency-version }}
+    name: P${{ matrix.php }} - ${{ matrix.dependency-version }} - ${{ matrix.operating-system }}
 
     steps:
       - uses: actions/checkout@v2
diff --git a/README.md b/README.md
index efb8a3f..4bf4724 100644
--- a/README.md
+++ b/README.md
@@ -144,6 +144,7 @@ This will prevent any method name conflicts with core, your custom or other trai
 \Astrotomic\PhpunitAssertions\PathAssertions::assertBasename('image.jpg', '/foo/bar/image.jpg');
 \Astrotomic\PhpunitAssertions\PathAssertions::assertFilename('image', '/foo/bar/image.jpg');
 \Astrotomic\PhpunitAssertions\PathAssertions::assertExtension('jpg', '/foo/bar/image.jpg');
+\Astrotomic\PhpunitAssertions\PathAssertions::assertOsAgnosticPath(__DIR__ . '/resources/css/main.css', __DIR__ . '\resources\css\main.css');
 ```
 
 ### UUID
diff --git a/src/PathAssertions.php b/src/PathAssertions.php
index fdf1261..f0e3913 100644
--- a/src/PathAssertions.php
+++ b/src/PathAssertions.php
@@ -31,4 +31,23 @@ public static function assertComponent($expected, $actual, int $component): void
         PHPUnit::assertIsString($actual);
         PHPUnit::assertSame($expected, pathinfo($actual, $component));
     }
+
+    private static function agnosticPath(string $path): string
+    {
+        if (DIRECTORY_SEPARATOR === '/') {
+            if (str_contains($path, '\\')) {
+                return str_replace('\\', DIRECTORY_SEPARATOR, $path);
+            }
+            return $path;
+        }
+
+        return str_replace('/', DIRECTORY_SEPARATOR, $path);
+    }
+
+    public static function assertOsAgnosticPath(string $expected, $actual): void
+    {
+        $osNormalizedExpected = PathAssertions::agnosticPath($expected);
+        PHPUnit::assertIsString($actual);
+        PHPUnit::assertSame($osNormalizedExpected, $actual);
+    }
 }
diff --git a/tests/PathAssertionsTest.php b/tests/PathAssertionsTest.php
index f08a060..1b5cf31 100644
--- a/tests/PathAssertionsTest.php
+++ b/tests/PathAssertionsTest.php
@@ -57,4 +57,30 @@ public static function it_can_validate_extension(): void
 
         PathAssertions::assertExtension($extension, $directory.'/'.$filename.'.'.$extension);
     }
+
+    /**
+     * Detect the OS of the PHP in use and return a path with opposite DIR seperator.
+     *
+     * When given the rand: true parameter it will sometimes provide mixed results.
+     */
+    private static function os_agnostic_get_expected_path(bool $rand = false): string
+    {
+        // Intentionally set the "expected" path to opposite of what should work on the platform.
+        if (PHP_OS_FAMILY !== "Windows" || ($rand === true && 1 === self::randomInt(0, 4))) {
+            return dirname(__DIR__) . '\tests\Utils';
+        }
+
+        return dirname(__DIR__) . '/tests/Utils';
+    }
+
+    /**
+     * @test
+     * @dataProvider hundredTimes
+     */
+    public static function it_can_validate_os_agnostic_paths(): void
+    {
+        $expected = static::os_agnostic_get_expected_path(true);
+        static::assertNotEquals($expected, realpath(dirname(__DIR__) . '/tests/Utils'));
+        PathAssertions::assertOsAgnosticPath($expected, realpath(dirname(__DIR__) . '/tests/Utils'));
+    }
 }