diff --git a/src/PendingObjects/TestCall.php b/src/PendingObjects/TestCall.php
index 40574ed13..41d85826e 100644
--- a/src/PendingObjects/TestCall.php
+++ b/src/PendingObjects/TestCall.php
@@ -144,11 +144,9 @@ public function skip($conditionOrMessage = true, string $message = ''): TestCall
             ? $conditionOrMessage
             : $message;
 
-        if ($condition() !== false) {
-            $this->testCaseFactory
-                ->chains
-                ->add(Backtrace::file(), Backtrace::line(), 'markTestSkipped', [$message]);
-        }
+        $this->testCaseFactory
+            ->chains
+            ->addWhen($condition, Backtrace::file(), Backtrace::line(), 'markTestSkipped', [$message]);
 
         return $this;
     }
diff --git a/src/Support/HigherOrderMessage.php b/src/Support/HigherOrderMessage.php
index 2a51b7ba0..78820dc38 100644
--- a/src/Support/HigherOrderMessage.php
+++ b/src/Support/HigherOrderMessage.php
@@ -4,6 +4,7 @@
 
 namespace Pest\Support;
 
+use Closure;
 use ReflectionClass;
 use Throwable;
 
@@ -50,6 +51,13 @@ final class HigherOrderMessage
      */
     public $arguments;
 
+    /**
+     * An optional condition that will determine if the message will be executed.
+     *
+     * @var callable(): bool|null
+     */
+    public $condition = null;
+
     /**
      * Creates a new higher order message.
      *
@@ -70,6 +78,11 @@ public function __construct(string $filename, int $line, string $methodName, arr
      */
     public function call(object $target)
     {
+        /* @phpstan-ignore-next-line */
+        if (is_callable($this->condition) && call_user_func(Closure::bind($this->condition, $target)) === false) {
+            return $target;
+        }
+
         if ($this->hasHigherOrderCallable()) {
             /* @phpstan-ignore-next-line */
             return (new HigherOrderCallables($target))->{$this->methodName}(...$this->arguments);
@@ -93,6 +106,18 @@ public function call(object $target)
         }
     }
 
+    /**
+     * Indicates that this message should only be called when the given condition is true.
+     *
+     * @param callable(): bool $condition
+     */
+    public function when(callable $condition): self
+    {
+        $this->condition = $condition;
+
+        return $this;
+    }
+
     /**
      * Determines whether or not there exists a higher order callable with the message name.
      *
diff --git a/src/Support/HigherOrderMessageCollection.php b/src/Support/HigherOrderMessageCollection.php
index f16765e1c..4c6e9cd26 100644
--- a/src/Support/HigherOrderMessageCollection.php
+++ b/src/Support/HigherOrderMessageCollection.php
@@ -24,6 +24,16 @@ public function add(string $filename, int $line, string $methodName, array $argu
         $this->messages[] = new HigherOrderMessage($filename, $line, $methodName, $arguments);
     }
 
+    /**
+     * Adds a new higher order message to the collection if the callable condition is does not return false.
+     *
+     * @param array<int, mixed> $arguments
+     */
+    public function addWhen(callable $condition, string $filename, int $line, string $methodName, array $arguments): void
+    {
+        $this->messages[] = (new HigherOrderMessage($filename, $line, $methodName, $arguments))->when($condition);
+    }
+
     /**
      * Proxy all the messages starting from the target.
      */
diff --git a/tests/Features/Skip.php b/tests/Features/Skip.php
index 66d6fe627..f5d867ca9 100644
--- a/tests/Features/Skip.php
+++ b/tests/Features/Skip.php
@@ -1,5 +1,9 @@
 <?php
 
+beforeEach(function () {
+    $this->shouldSkip = true;
+});
+
 it('do not skips')
     ->skip(false)
     ->assertTrue(true);
@@ -31,3 +35,12 @@
 it('skips when skip after assertion')
     ->assertTrue(true)
     ->skip();
+
+it('can use something in the test case as a condition')
+    ->skip(function () { return $this->shouldSkip; }, 'This test was skipped')
+    ->assertTrue(false);
+
+it('can user higher order callables and skip')
+    ->skip(function () { return $this->shouldSkip; })
+    ->expect(function () { return $this->shouldSkip; })
+    ->toBeFalse();