diff --git a/docs/validating-tokens.md b/docs/validating-tokens.md
index 7e130db9e..a833502b7 100644
--- a/docs/validating-tokens.md
+++ b/docs/validating-tokens.md
@@ -85,6 +85,7 @@ This library provides the following constraints:
 * `Lcobucci\JWT\Validation\Constraint\PermittedFor`: verifies if the claim `aud` contains the expected value
 * `Lcobucci\JWT\Validation\Constraint\RelatedTo`: verifies if the claim `sub` matches the expected value
 * `Lcobucci\JWT\Validation\Constraint\SignedWith`: verifies if the token was signed with the expected signer and key
+* `Lcobucci\JWT\Validation\Constraint\SignedWithOneInSet`: verifies the token signature against multiple `SignedWith` constraints
 * `Lcobucci\JWT\Validation\Constraint\StrictValidAt`: verifies presence and validity of the claims `iat`, `nbf`, and `exp` (supports leeway configuration)
 * `Lcobucci\JWT\Validation\Constraint\LooseValidAt`: verifies the claims `iat`, `nbf`, and `exp`, when present (supports leeway configuration)
 * `Lcobucci\JWT\Validation\Constraint\HasClaimWithValue`: verifies that a **custom claim** has the expected value (not recommended when comparing cryptographic hashes)
diff --git a/src/Validation/Constraint/SignedWithOneInSet.php b/src/Validation/Constraint/SignedWithOneInSet.php
new file mode 100644
index 000000000..4e0fe0be6
--- /dev/null
+++ b/src/Validation/Constraint/SignedWithOneInSet.php
@@ -0,0 +1,39 @@
+<?php
+declare(strict_types=1);
+
+namespace Lcobucci\JWT\Validation\Constraint;
+
+use Lcobucci\JWT\Token;
+use Lcobucci\JWT\Validation\ConstraintViolation;
+use Lcobucci\JWT\Validation\SignedWith as SignedWithInterface;
+
+use const PHP_EOL;
+
+final class SignedWithOneInSet implements SignedWithInterface
+{
+    /** @var array<SignedWithInterface> */
+    private readonly array $constraints;
+
+    public function __construct(SignedWithInterface ...$constraints)
+    {
+        $this->constraints = $constraints;
+    }
+
+    public function assert(Token $token): void
+    {
+        $errorMessage = 'It was not possible to verify the signature of the token, reasons:';
+
+        foreach ($this->constraints as $constraint) {
+            try {
+                $constraint->assert($token);
+
+                return;
+            } catch (ConstraintViolation $violation) {
+                $errorMessage .= PHP_EOL . '- ' . $violation->getMessage()
+                    . ' (verified by ' . $violation->constraint . ')';
+            }
+        }
+
+        throw ConstraintViolation::error($errorMessage, $this);
+    }
+}
diff --git a/tests/JwtFacadeTest.php b/tests/JwtFacadeTest.php
index ed3caea43..c9de4345a 100644
--- a/tests/JwtFacadeTest.php
+++ b/tests/JwtFacadeTest.php
@@ -14,14 +14,15 @@
 use Lcobucci\JWT\Token\Plain;
 use Lcobucci\JWT\Validation\Constraint\IssuedBy;
 use Lcobucci\JWT\Validation\Constraint\SignedWith;
+use Lcobucci\JWT\Validation\Constraint\SignedWithOneInSet;
 use Lcobucci\JWT\Validation\Constraint\StrictValidAt;
 use Lcobucci\JWT\Validation\RequiredConstraintsViolated;
+use PHPUnit\Framework\Attributes as PHPUnit;
 use PHPUnit\Framework\TestCase;
 use Psr\Clock\ClockInterface;
 
 /**
- * @covers ::__construct
- * @coversDefaultClass \Lcobucci\JWT\JwtFacade
+ * @covers \Lcobucci\JWT\JwtFacade
  *
  * @uses  \Lcobucci\JWT\Token\Parser
  * @uses  \Lcobucci\JWT\Encoding\JoseEncoder
@@ -40,6 +41,7 @@
  * @uses  \Lcobucci\JWT\Validation\Validator
  * @uses  \Lcobucci\JWT\Validation\Constraint\IssuedBy
  * @uses  \Lcobucci\JWT\Validation\Constraint\SignedWith
+ * @uses  \Lcobucci\JWT\Validation\Constraint\SignedWithOneInSet
  * @uses  \Lcobucci\JWT\Validation\Constraint\StrictValidAt
  * @uses  \Lcobucci\JWT\Validation\ConstraintViolation
  * @uses  \Lcobucci\JWT\Validation\RequiredConstraintsViolated
@@ -72,12 +74,7 @@ private function createToken(): string
         )->toString();
     }
 
-    /**
-     * @test
-     *
-     * @covers ::issue
-     * @covers ::parse
-     */
+    #[PHPUnit\Test]
     public function issueSetTimeValidity(): void
     {
         $token = (new JwtFacade(clock: $this->clock))->issue(
@@ -105,12 +102,7 @@ public function issueSetTimeValidity(): void
         self::assertTrue($token->isExpired($inOneYear));
     }
 
-    /**
-     * @test
-     *
-     * @covers ::issue
-     * @covers ::parse
-     */
+    #[PHPUnit\Test]
     public function issueAllowsTimeValidityOverwrite(): void
     {
         $then  = new DateTimeImmutable('2001-02-03 04:05:06');
@@ -144,12 +136,7 @@ static function (Builder $builder) use ($then): Builder {
         self::assertTrue($token->isExpired($inOneYear));
     }
 
-    /**
-     * @test
-     *
-     * @covers ::issue
-     * @covers ::parse
-     */
+    #[PHPUnit\Test]
     public function goodJwt(): void
     {
         $token = (new JwtFacade())->parse(
@@ -162,12 +149,7 @@ public function goodJwt(): void
         self::assertInstanceOf(Plain::class, $token);
     }
 
-    /**
-     * @test
-     *
-     * @covers ::issue
-     * @covers ::parse
-     */
+    #[PHPUnit\Test]
     public function badSigner(): void
     {
         $this->expectException(RequiredConstraintsViolated::class);
@@ -181,12 +163,7 @@ public function badSigner(): void
         );
     }
 
-    /**
-     * @test
-     *
-     * @covers ::issue
-     * @covers ::parse
-     */
+    #[PHPUnit\Test]
     public function badKey(): void
     {
         $this->expectException(RequiredConstraintsViolated::class);
@@ -200,12 +177,7 @@ public function badKey(): void
         );
     }
 
-    /**
-     * @test
-     *
-     * @covers ::issue
-     * @covers ::parse
-     */
+    #[PHPUnit\Test]
     public function badTime(): void
     {
         $token = $this->createToken();
@@ -222,12 +194,7 @@ public function badTime(): void
         );
     }
 
-    /**
-     * @test
-     *
-     * @covers ::issue
-     * @covers ::parse
-     */
+    #[PHPUnit\Test]
     public function badIssuer(): void
     {
         $this->expectException(RequiredConstraintsViolated::class);
@@ -241,11 +208,7 @@ public function badIssuer(): void
         );
     }
 
-    /**
-     * @test
-     *
-     * @covers ::parse
-     */
+    #[PHPUnit\Test]
     public function parserForNonUnencryptedTokens(): void
     {
         $this->expectException(AssertionError::class);
@@ -258,12 +221,7 @@ public function parserForNonUnencryptedTokens(): void
         );
     }
 
-    /**
-     * @test
-     *
-     * @covers ::issue
-     * @covers ::parse
-     */
+    #[PHPUnit\Test]
     public function customPsrClock(): void
     {
         $clock = new class () implements ClockInterface {
@@ -290,4 +248,20 @@ public function now(): DateTimeImmutable
             ),
         );
     }
+
+    #[PHPUnit\Test]
+    public function multipleKeys(): void
+    {
+        $token = (new JwtFacade())->parse(
+            $this->createToken(),
+            new SignedWithOneInSet(
+                new SignedWith($this->signer, InMemory::base64Encoded('czyPTpN595zVNSuvoNNlXCRFgXS2fHscMR36dGojaUE=')),
+                new SignedWith($this->signer, $this->key),
+            ),
+            new StrictValidAt($this->clock),
+            new IssuedBy($this->issuer),
+        );
+
+        self::assertInstanceOf(Plain::class, $token);
+    }
 }
diff --git a/tests/Validation/Constraint/SignedWithOneInSetTest.php b/tests/Validation/Constraint/SignedWithOneInSetTest.php
new file mode 100644
index 000000000..38245956e
--- /dev/null
+++ b/tests/Validation/Constraint/SignedWithOneInSetTest.php
@@ -0,0 +1,75 @@
+<?php
+declare(strict_types=1);
+
+namespace Lcobucci\JWT\Tests\Validation\Constraint;
+
+use Lcobucci\JWT\Signer\Key\InMemory;
+use Lcobucci\JWT\Token;
+use Lcobucci\JWT\Token\DataSet;
+use Lcobucci\JWT\Token\Plain;
+use Lcobucci\JWT\Token\Signature;
+use Lcobucci\JWT\Validation\Constraint\SignedWithOneInSet;
+use Lcobucci\JWT\Validation\ConstraintViolation;
+use Lcobucci\JWT\Validation\SignedWith;
+use PHPUnit\Framework\Attributes as PHPUnit;
+
+use const PHP_EOL;
+
+#[PHPUnit\CoversClass(SignedWithOneInSet::class)]
+#[PHPUnit\CoversClass(ConstraintViolation::class)]
+#[PHPUnit\UsesClass(DataSet::class)]
+#[PHPUnit\UsesClass(InMemory::class)]
+#[PHPUnit\UsesClass(Plain::class)]
+#[PHPUnit\UsesClass(Signature::class)]
+#[PHPUnit\UsesClass(SignedWith::class)]
+final class SignedWithOneInSetTest extends ConstraintTestCase
+{
+    #[PHPUnit\Test]
+    public function exceptionShouldBeRaisedWhenSignatureIsNotVerifiedByAllConstraints(): void
+    {
+        $token = $this->createMock(Token::class);
+
+        $verifySignature1 = $this->createMock(SignedWith::class);
+        $verifySignature1
+            ->expects(self::once())
+            ->method('assert')
+            ->willThrowException(ConstraintViolation::error('Msg1', $verifySignature1));
+
+        $verifySignature2 = $this->createMock(SignedWith::class);
+        $verifySignature2
+            ->expects(self::once())
+            ->method('assert')
+            ->willThrowException(ConstraintViolation::error('Msg2', $verifySignature2));
+
+        $constraint = new SignedWithOneInSet($verifySignature1, $verifySignature2);
+
+        $this->expectException(ConstraintViolation::class);
+        $this->expectExceptionMessage(
+            'It was not possible to verify the signature of the token, reasons:'
+            . PHP_EOL . '- Msg1 (verified by ' . $verifySignature1::class . ')'
+            . PHP_EOL . '- Msg2 (verified by ' . $verifySignature2::class . ')',
+        );
+
+        $constraint->assert($token);
+    }
+
+    #[PHPUnit\Test]
+    public function assertShouldNotRaiseExceptionsWhenSignatureIsVerifiedByAtLeastOneConstraint(): void
+    {
+        $token = $this->createMock(Token::class);
+
+        $verifySignature1 = $this->createMock(SignedWith::class);
+        $verifySignature1
+            ->expects(self::once())
+            ->method('assert')
+            ->willThrowException(ConstraintViolation::error('Msg', $verifySignature1));
+
+        $verifySignature2 = $this->createMock(SignedWith::class);
+        $verifySignature2->expects(self::once())->method('assert');
+
+        $constraint = new SignedWithOneInSet($verifySignature1, $verifySignature2);
+        $constraint->assert($token);
+
+        $this->addToAssertionCount(1);
+    }
+}