diff --git a/src/Expectation.php b/src/Expectation.php
index 253b1e1e..b229416a 100644
--- a/src/Expectation.php
+++ b/src/Expectation.php
@@ -154,9 +154,10 @@ final class Expectation
             throw new BadMethodCallException('Expectation value is not iterable.');
         }
 
-        $value  = is_array($this->value) ? $this->value : iterator_to_array($this->value);
-        $keys   = array_keys($value);
-        $values = array_values($value);
+        $value          = is_array($this->value) ? $this->value : iterator_to_array($this->value);
+        $keys           = array_keys($value);
+        $values         = array_values($value);
+        $callbacksCount = count($callbacks);
 
         $index = 0;
 
@@ -165,6 +166,10 @@ final class Expectation
             $index       = $index < count($values) - 1 ? $index + 1 : 0;
         }
 
+        if ($callbacksCount > count($values)) {
+            Assert::assertLessThanOrEqual(count($value), count($callbacks));
+        }
+
         foreach ($values as $key => $item) {
             if (is_callable($callbacks[$key])) {
                 call_user_func($callbacks[$key], new self($item), new self($keys[$key]));
@@ -177,6 +182,88 @@ final class Expectation
         return $this;
     }
 
+    /**
+     * If the subject matches one of the given "expressions", the expression callback will run.
+     *
+     * @template TMatchSubject of array-key
+     *
+     * @param callable(): TMatchSubject|TMatchSubject $subject
+     * @param array<TMatchSubject, (callable(Expectation<TValue>): mixed)|TValue> $expressions
+     */
+    public function match($subject, array $expressions): Expectation
+    {
+        $subject = is_callable($subject)
+            ? $subject
+            : function () use ($subject) {
+                return $subject;
+            };
+
+        $subject   = $subject();
+
+        $matched = false;
+
+        foreach ($expressions as $key => $callback) {
+            if ($subject != $key) {
+                continue;
+            }
+
+            $matched = true;
+
+            if (is_callable($callback)) {
+                $callback(new self($this->value));
+                continue;
+            }
+
+            $this->and($this->value)->toEqual($callback);
+
+            break;
+        }
+
+        if ($matched === false) {
+            throw new ExpectationFailedException('Unhandled match value.');
+        }
+
+        return $this;
+    }
+
+    /**
+     * Apply the callback if the given "condition" is falsy.
+     *
+     * @param  (callable(): bool)|bool $condition
+     * @param callable(Expectation<TValue>): mixed $callback
+     */
+    public function unless($condition, callable $callback): Expectation
+    {
+        $condition = is_callable($condition)
+            ? $condition
+            : static function () use ($condition): mixed {
+                return $condition;
+            };
+
+        return $this->when(!$condition(), $callback);
+    }
+
+    /**
+     * Apply the callback if the given "condition" is truthy.
+     *
+     * @param  (callable(): bool)|bool $condition
+     * @param callable(Expectation<TValue>): mixed $callback
+     */
+    public function when($condition, callable $callback): Expectation
+    {
+        $condition = is_callable($condition)
+            ? $condition
+            : static function () use ($condition): mixed {
+                return $condition;
+            };
+
+        if ($condition()) {
+            $callback($this->and($this->value));
+        }
+
+        return $this;
+    }
+
     /**
      * Asserts that two variables have the same type and
      * value. Used on objects, it asserts that two
diff --git a/src/PendingObjects/TestCall.php b/src/PendingObjects/TestCall.php
index be839bff..287ca7a9 100644
--- a/src/PendingObjects/TestCall.php
+++ b/src/PendingObjects/TestCall.php
@@ -78,6 +78,26 @@ final class TestCall
         return $this;
     }
 
+    /**
+     * Asserts that the test throws the given `$exceptionClass` when called if the given condition is true.
+     *
+     * @param (callable(): bool)|bool $condition
+     */
+    public function throwsIf($condition, string $exception, string $exceptionMessage = null): TestCall
+    {
+        $condition = is_callable($condition)
+            ? $condition
+            : static function () use ($condition): mixed {
+                return $condition;
+            };
+
+        if ($condition()) {
+            return $this->throws($exception, $exceptionMessage);
+        }
+
+        return $this;
+    }
+
     /**
      * Runs the current test multiple times with
      * each item of the given `iterable`.
diff --git a/tests/.snapshots/success.txt b/tests/.snapshots/success.txt
index d7a866b9..addf3536 100644
--- a/tests/.snapshots/success.txt
+++ b/tests/.snapshots/success.txt
@@ -107,6 +107,11 @@
   ✓ it catch exceptions
   ✓ it catch exceptions and messages
   ✓ it can just define the message
+  ✓ it not catch exceptions if given condition is false
+  ✓ it catch exceptions if given condition is true
+  ✓ it catch exceptions and messages if given condition is true
+  ✓ it can just define the message if given condition is true
+  ✓ it can just define the message if given condition is 1
 
    PASS  Tests\Features\Expect\HigherOrder\methods
   ✓ it can access methods
@@ -158,6 +163,17 @@
   ✓ it properly parses json string
   ✓ fails with broken json string
 
+   PASS  Tests\Features\Expect\matchExpectation
+  ✓ it pass
+  ✓ it failures
+  ✓ it runs with truthy
+  ✓ it runs with falsy
+  ✓ it runs with truthy closure condition
+  ✓ it runs with falsy closure condition
+  ✓ it can be passed non-callable values
+  ✓ it fails with unhandled match
+  ✓ it can be used in higher order tests
+
    PASS  Tests\Features\Expect\not
   ✓ not property calls
 
@@ -168,7 +184,7 @@
   ✓ an exception is thrown if the the type is not iterable
   ✓ allows for sequences of checks to be run on iterable data
   ✓ loops back to the start if it runs out of sequence items
-  ✓ it works if the number of items in the iterable is smaller than the number of expectations
+  ✓ fails if the number of iterable items is greater than the number of expectations
   ✓ it works with associative arrays
   ✓ it can be passed non-callable values
   ✓ it can be passed a mixture of value types
@@ -481,6 +497,24 @@
   ✓ closure missing parameter
   ✓ closure missing type-hint
 
+   PASS  Tests\Features\Expect\unless
+  ✓ it pass
+  ✓ it failures
+  ✓ it runs with truthy
+  ✓ it skips with falsy
+  ✓ it runs with truthy closure condition
+  ✓ it skips with falsy closure condition
+  ✓ it can be used in higher order tests
+
+   PASS  Tests\Features\Expect\when
+  ✓ it pass
+  ✓ it failures
+  ✓ it runs with truthy
+  ✓ it skips with falsy
+  ✓ it runs with truthy closure condition
+  ✓ it skips with falsy closure condition
+  ✓ it can be used in higher order tests
+
    PASS  Tests\Features\Helpers
   ✓ it can set/get properties on $this
   ✓ it throws error if property do not exist
@@ -623,10 +657,6 @@
   ✓ it show the actual dataset of multiple non-named datasets in their description
   ✓ it show the correct description for mixed named and not-named datasets
 
-   PASS  Tests\Unit\Plugins\Context
-  ✓ environment is set to CI when --ci option is used
-  ✓ environment is set to Local when --ci option is not used
-
    PASS  Tests\Unit\Plugins\Version
   ✓ it outputs the version when --version is used
   ✓ it do not outputs version when --version is not used
@@ -652,7 +682,6 @@
   ✓ it alerts users about tests with arguments but no input
   ✓ it can return an array of all test suite filenames
   ✓ it can filter the test suite filenames to those with the only method
-  ✓ it does not filter the test suite filenames to those with the only method when working in CI pipeline
 
    PASS  Tests\Visual\Help
   ✓ visual snapshot of help command output
@@ -686,5 +715,5 @@
   ✓ it is a test
   ✓ it uses correct parent class
 
-  Tests:  4 incompleted, 9 skipped, 450 passed
+  Tests:  4 incompleted, 9 skipped, 475 passed
   
\ No newline at end of file
diff --git a/tests/Features/Exceptions.php b/tests/Features/Exceptions.php
index 37eaaeb9..9970c2a9 100644
--- a/tests/Features/Exceptions.php
+++ b/tests/Features/Exceptions.php
@@ -17,3 +17,23 @@ it('catch exceptions and messages', function () {
 it('can just define the message', function () {
     throw new Exception('Something bad happened');
 })->throws('Something bad happened');
+
+it('not catch exceptions if given condition is false', function () {
+    $this->assertTrue(true);
+})->throwsIf(false, Exception::class);
+
+it('catch exceptions if given condition is true', function () {
+    throw new Exception('Something bad happened');
+})->throwsIf(function () { return true; }, Exception::class);
+
+it('catch exceptions and messages if given condition is true', function () {
+    throw new Exception('Something bad happened');
+})->throwsIf(true, Exception::class, 'Something bad happened');
+
+it('can just define the message if given condition is true', function () {
+    throw new Exception('Something bad happened');
+})->throwsIf(true, 'Something bad happened');
+
+it('can just define the message if given condition is 1', function () {
+    throw new Exception('Something bad happened');
+})->throwsIf(1, 'Something bad happened');
diff --git a/tests/Features/Expect/matchExpectation.php b/tests/Features/Expect/matchExpectation.php
new file mode 100644
index 00000000..2bea1be5
--- /dev/null
+++ b/tests/Features/Expect/matchExpectation.php
@@ -0,0 +1,148 @@
+<?php
+
+use PHPUnit\Framework\ExpectationFailedException;
+
+beforeEach(function () {
+    $this->matched = null;
+});
+
+it('pass', function () {
+    expect('baz')
+        ->match('foo', [
+                'bar' => function ($value) {
+                    $this->matched = 'bar';
+
+                    return $value->toEqual('bar');
+                },
+                'foo' => function ($value) {
+                    $this->matched = 'baz';
+
+                    return $value->toEqual('baz');
+                },
+            ]
+        )
+        ->toEqual($this->matched);
+
+    expect(static::getCount())->toBe(2);
+});
+
+it('failures', function () {
+    expect(true)
+        ->match('foo', [
+                'bar' => function ($value) {
+                    return $value->toBeTrue();
+                },
+                'foo' => function ($value) {
+                    return $value->toBeFalse();
+                },
+            ]
+        );
+})->throws(ExpectationFailedException::class, 'true is false');
+
+it('runs with truthy', function () {
+    expect('foo')
+        ->match(1, [
+                'bar' => function ($value) {
+                    $this->matched = 'bar';
+
+                    return $value->toEqual('bar');
+                },
+                true => function ($value) {
+                    $this->matched = 'foo';
+
+                    return $value->toEqual('foo');
+                },
+            ]
+        )
+        ->toEqual($this->matched);
+
+    expect(static::getCount())->toBe(2);
+});
+
+it('runs with falsy', function () {
+    expect('foo')
+        ->match(false, [
+                'bar' => function ($value) {
+                    $this->matched = 'bar';
+
+                    return $value->toEqual('bar');
+                },
+                false => function ($value) {
+                    $this->matched = 'foo';
+
+                    return $value->toEqual('foo');
+                },
+            ]
+        )
+        ->toEqual($this->matched);
+
+    expect(static::getCount())->toBe(2);
+});
+
+it('runs with truthy closure condition', function () {
+    expect('foo')
+        ->match(
+            function () { return '1'; }, [
+                'bar' => function ($value) {
+                    $this->matched = 'bar';
+
+                    return $value->toEqual('bar');
+                },
+                true => function ($value) {
+                    $this->matched = 'foo';
+
+                    return $value->toEqual('foo');
+                },
+            ]
+        )
+        ->toEqual($this->matched);
+
+    expect(static::getCount())->toBe(2);
+});
+
+it('runs with falsy closure condition', function () {
+    expect('foo')
+        ->match(
+            function () { return '0'; }, [
+                'bar' => function ($value) {
+                    $this->matched = 'bar';
+
+                    return $value->toEqual('bar');
+                },
+                false => function ($value) {
+                    $this->matched = 'foo';
+
+                    return $value->toEqual('foo');
+                },
+            ]
+        )
+        ->toEqual($this->matched);
+
+    expect(static::getCount())->toBe(2);
+});
+
+it('can be passed non-callable values', function () {
+    expect('foo')
+        ->match('pest', [
+                'bar'  => 'foo',
+                'pest' => 'baz',
+            ]
+        );
+})->throws(ExpectationFailedException::class, 'two strings are equal');
+
+it('fails with unhandled match', function () {
+    expect('foo')->match('bar', []);
+})->throws(ExpectationFailedException::class, 'Unhandled match value.');
+
+it('can be used in higher order tests')
+    ->expect(true)
+    ->match(
+        function () { return true; }, [
+            false => function ($value) {
+                return $value->toBeFalse();
+            },
+            true => function ($value) {
+                return $value->toBeTrue();
+            },
+        ]
+    );
diff --git a/tests/Features/Expect/sequence.php b/tests/Features/Expect/sequence.php
index b4f82cb5..4f11b3a3 100644
--- a/tests/Features/Expect/sequence.php
+++ b/tests/Features/Expect/sequence.php
@@ -1,5 +1,7 @@
 <?php
 
+use PHPUnit\Framework\ExpectationFailedException;
+
 test('an exception is thrown if the the type is not iterable', function () {
     expect('Foobar')->each->sequence();
 })->throws(BadMethodCallException::class, 'Expectation value is not iterable.');
@@ -26,16 +28,14 @@ test('loops back to the start if it runs out of sequence items', function () {
     expect(static::getCount())->toBe(16);
 });
 
-test('it works if the number of items in the iterable is smaller than the number of expectations', function () {
+test('fails if the number of iterable items is greater than the number of expectations', function () {
     expect([1, 2])
         ->sequence(
             function ($expectation) { $expectation->toBeInt()->toEqual(1); },
             function ($expectation) { $expectation->toBeInt()->toEqual(2); },
             function ($expectation) { $expectation->toBeInt()->toEqual(3); },
         );
-
-    expect(static::getCount())->toBe(4);
-});
+})->throws(ExpectationFailedException::class);
 
 test('it works with associative arrays', function () {
     expect(['foo' => 'bar', 'baz' => 'boom'])
diff --git a/tests/Features/Expect/unless.php b/tests/Features/Expect/unless.php
new file mode 100644
index 00000000..9f11c7ef
--- /dev/null
+++ b/tests/Features/Expect/unless.php
@@ -0,0 +1,101 @@
+<?php
+
+use PHPUnit\Framework\ExpectationFailedException;
+
+beforeEach(function () {
+    $this->unlessObject = new stdClass();
+    $this->unlessObject->trueValue = true;
+    $this->unlessObject->foo = 'foo';
+});
+
+it('pass', function () {
+    expect('foo')
+        ->unless(
+            true,
+            function ($value) {
+                return $value->toEqual('bar');
+            }
+        )
+        ->toEqual('foo');
+
+    expect(static::getCount())->toBe(1);
+});
+
+it('failures', function () {
+    expect('foo')
+        ->unless(
+            false,
+            function ($value) {
+                return $value->toBeTrue();
+            }
+        )
+        ->toEqual('foo');
+})->throws(ExpectationFailedException::class, 'is true');
+
+it('runs with truthy', function () {
+    expect($this->unlessObject)
+        ->unless(
+            0,
+            function ($value) {
+                return $value->trueValue->toBeTrue();
+            }
+        )
+        ->foo->toEqual('foo');
+
+    expect(static::getCount())->toBe(2);
+});
+
+it('skips with falsy', function () {
+    expect($this->unlessObject)
+        ->unless(
+            1,
+            function ($value) {
+                return $value->trueValue->toBeFalse(); // fails
+            }
+        )
+        ->unless(
+            true,
+            function ($value) {
+                return $value->trueValue->toBeFalse(); // fails
+            }
+        )
+        ->foo->toEqual('foo');
+
+    expect(static::getCount())->toBe(1);
+});
+
+it('runs with truthy closure condition', function () {
+    expect($this->unlessObject)
+        ->unless(
+            function () { return '0'; },
+            function ($value) {
+                return $value->trueValue->toBeTrue();
+            }
+        )
+        ->foo->toEqual('foo');
+
+    expect(static::getCount())->toBe(2);
+});
+
+it('skips with falsy closure condition', function () {
+    expect($this->unlessObject)
+        ->unless(
+            function () { return '1'; },
+            function ($value) {
+                return $value->trueValue->toBeFalse(); // fails
+            }
+        )
+        ->foo->toEqual('foo');
+
+    expect(static::getCount())->toBe(1);
+});
+
+it('can be used in higher order tests')
+    ->expect(true)
+    ->unless(
+        function () { return false; },
+        function ($value) {
+            return $value->toBeFalse();
+        }
+    )
+    ->throws(ExpectationFailedException::class, 'true is false');
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');