diff --git a/tests/Features/Expect/when.php b/tests/Features/Expect/when.php
new file mode 100644
index 00000000..db9fa4f1
--- /dev/null
+++ b/tests/Features/Expect/when.php
@@ -0,0 +1,101 @@
+<?php
+
+use PHPUnit\Framework\ExpectationFailedException;
+
+beforeEach(function () {
+    $this->whenObject = new stdClass();
+    $this->whenObject->trueValue = true;
+    $this->whenObject->foo = 'foo';
+});
+
+it('pass', function () {
+    expect('foo')
+        ->when(
+            true,
+            function ($value) {
+                return $value->toEqual('foo');
+            }
+        )
+        ->toEqual('foo');
+
+    expect(static::getCount())->toBe(2);
+});
+
+it('failures', function () {
+    expect('foo')
+        ->when(
+            true,
+            function ($value) {
+                return $value->toBeTrue();
+            }
+        )
+        ->toEqual('foo');
+})->throws(ExpectationFailedException::class, 'is true');
+
+it('runs with truthy', function () {
+    expect($this->whenObject)
+        ->when(
+            1,
+            function ($value) {
+                return $value->trueValue->toBeTrue();
+            }
+        )
+        ->foo->toEqual('foo');
+
+    expect(static::getCount())->toBe(2);
+});
+
+it('skips with falsy', function () {
+    expect($this->whenObject)
+        ->when(
+            0,
+            function ($value) {
+                return $value->trueValue->toBeFalse(); // fails
+            }
+        )
+        ->when(
+            false,
+            function ($value) {
+                return $value->trueValue->toBeFalse(); // fails
+            }
+        )
+        ->foo->toEqual('foo');
+
+    expect(static::getCount())->toBe(1);
+});
+
+it('runs with truthy closure condition', function () {
+    expect($this->whenObject)
+        ->when(
+            function () { return '1'; },
+            function ($value) {
+                return $value->trueValue->toBeTrue();
+            }
+        )
+        ->foo->toEqual('foo');
+
+    expect(static::getCount())->toBe(2);
+});
+
+it('skips with falsy closure condition', function () {
+    expect($this->whenObject)
+        ->when(
+            function () { return '0'; },
+            function ($value) {
+                return $value->trueValue->toBeFalse(); // fails
+            }
+        )
+        ->foo->toEqual('foo');
+
+    expect(static::getCount())->toBe(1);
+});
+
+it('can be used in higher order tests')
+    ->expect(false)
+    ->when(
+        function () { return true; },
+        function ($value) {
+            return $value->toBeTrue();
+        }
+    )
+    ->throws(ExpectationFailedException::class, 'false is true');