diff --git a/src/Expectation.php b/src/Expectation.php
index ebfd6302..11c04542 100644
--- a/src/Expectation.php
+++ b/src/Expectation.php
@@ -32,6 +32,7 @@
 use Pest\Support\ExpectationPipeline;
 use Pest\Support\Reflection;
 use PHPUnit\Architecture\Elements\ObjectDescription;
+use PHPUnit\Framework\AssertionFailedError;
 use PHPUnit\Framework\ExpectationFailedException;
 use ReflectionEnum;
 use ReflectionMethod;
@@ -324,6 +325,35 @@ public function when(callable|bool $condition, callable $callback): self
         return $this;
     }
 
+    public function toBeOneOf(Closure ...$tests): self
+    {
+        if ($tests === []) {
+            return $this;
+        }
+
+        $matches = [];
+        $exceptions = [];
+
+        foreach ($tests as $key => $test) {
+            try {
+                $test(new Expectation($this->value));
+                $matches[] = $key;
+            } catch (AssertionFailedError) {
+                $exceptions[] = $key;
+            }
+        }
+
+        if (count($matches) === 1) {
+            return $this;
+        }
+
+        if (count($matches) > 1) {
+            throw new ExpectationFailedException('Failed asserting value matches exactly one expectation (matches: '.implode(', ', $matches).').');
+        }
+
+        throw new ExpectationFailedException('Failed asserting value matches any expectations.');
+    }
+
     /**
      * Dynamically calls methods on the class or creates a new higher order expectation.
      *
diff --git a/tests/Features/Expect/toBeOneOf.php b/tests/Features/Expect/toBeOneOf.php
new file mode 100644
index 00000000..071b35ce
--- /dev/null
+++ b/tests/Features/Expect/toBeOneOf.php
@@ -0,0 +1,40 @@
+<?php
+
+use PHPUnit\Framework\ExpectationFailedException;
+
+expect(true)->toBeTrue()->and(false)->toBeFalse();
+
+test('risky with no assertions', function () {
+    expect(1)->toBeOneOf();
+})->throwsNoExceptions();
+
+test('to be one of', function () {
+    expect(1)->toBeOneOf(fn ($e) => $e->toBe(1), fn ($e) => $e->toBe(2), fn ($e) => $e->toBe(3));
+});
+
+test('it does not short-circuit', function () {
+    $executed = 0;
+    expect(1)->toBeOneOf(function ($e) use (&$executed) {
+        $executed++;
+
+        return $e->toBe(1);
+    }, function ($e) use (&$executed) {
+        $executed++;
+
+        return $e->toBe(2);
+    }, function ($e) use (&$executed) {
+        $executed++;
+
+        return $e->toBe(3);
+    });
+
+    expect($executed)->toBe(3);
+});
+
+test('failure with multiple matches', function () {
+    expect(1)->toBeOneOf(fn ($e) => $e->toBe(1), fn ($e) => $e->toBe(1));
+})->throws(ExpectationFailedException::class, 'Failed asserting value matches exactly one expectation (matches: 0, 1).');
+
+test('failure with no matches', function () {
+    expect(1)->toBeOneOf(fn ($e) => $e->toBe(2), fn ($e) => $e->toBe(2));
+})->throws(ExpectationFailedException::class, 'Failed asserting value matches any expectations.');