diff --git a/src/Appwrite/Utopia/Response/Model/ResourceToken.php b/src/Appwrite/Utopia/Response/Model/ResourceToken.php
index ef186c3d0b..73c3efee72 100644
--- a/src/Appwrite/Utopia/Response/Model/ResourceToken.php
+++ b/src/Appwrite/Utopia/Response/Model/ResourceToken.php
@@ -61,24 +61,40 @@ class ResourceToken extends Model
 
     public function filter(Document $document): Document
     {
-        $maxAge = PHP_INT_MAX;
         $expire = $document->getAttribute('expire');
-
+        $now = new \DateTime();
+        
+        // Calculate expiration timestamp for JWT
+        $expTimestamp = null;
         if ($expire !== null) {
-            $now = new \DateTime();
             $expiryDate = new \DateTime($expire);
-
-            // set 1 min if expired, we check for expiry later on route hooks for validation!
-            $maxAge = min(60, $expiryDate->getTimestamp() - $now->getTimestamp());
+            $secondsUntilExpiry = $expiryDate->getTimestamp() - $now->getTimestamp();
+            
+            // If token is expired, set expiration to 1 minute from now
+            // We check for actual expiry later on route hooks for validation
+            if ($secondsUntilExpiry <= 0) {
+                $expTimestamp = $now->getTimestamp() + 60;
+            } else {
+                $expTimestamp = $expiryDate->getTimestamp();
+            }
         }
 
-        $jwt = new JWT(System::getEnv('_APP_OPENSSL_KEY_V1'), 'HS256', $maxAge, 10);
-        $secret = $jwt->encode([
+        // Use maxAge as fallback, but rely on exp in payload for actual expiration
+        $jwt = new JWT(System::getEnv('_APP_OPENSSL_KEY_V1'), 'HS256', PHP_INT_MAX, 10);
+        
+        $payload = [
             'tokenId' => $document->getId(),
             'resourceId' => $document->getAttribute('resourceId'),
             'resourceType' => $document->getAttribute('resourceType'),
             'resourceInternalId' => $document->getAttribute('resourceInternalId'),
-        ]);
+        ];
+        
+        // Set explicit expiration in JWT payload if we have an expiry date
+        if ($expTimestamp !== null) {
+            $payload['exp'] = $expTimestamp;
+        }
+        
+        $secret = $jwt->encode($payload);
 
         $document->setAttribute('secret', $secret);
 
diff --git a/tests/e2e/Services/Tokens/TokensConsoleClientTest.php b/tests/e2e/Services/Tokens/TokensConsoleClientTest.php
index 4a7aab474a..d8bcd946ef 100644
--- a/tests/e2e/Services/Tokens/TokensConsoleClientTest.php
+++ b/tests/e2e/Services/Tokens/TokensConsoleClientTest.php
@@ -107,6 +107,44 @@ class TokensConsoleClientTest extends Scope
         return $data;
     }
 
+    /**
+     * @depends testCreateToken
+     */
+    public function testExpiredTokenJWT(array $data): array
+    {
+        $fileId = $data['fileId'];
+        $bucketId = $data['bucketId'];
+
+        // Create a token with an expiry date in the past (expired)
+        $pastExpiry = DateTime::addSeconds(new \DateTime(), -3600); // 1 hour ago
+        $expiredToken = $this->client->call(Client::METHOD_POST, '/tokens/buckets/' . $bucketId . '/files/' . $fileId, array_merge([
+            'content-type' => 'application/json',
+            'x-appwrite-project' => $this->getProject()['$id']
+        ], $this->getHeaders()), [
+            'expire' => $pastExpiry,
+        ]);
+
+        $this->assertEquals(201, $expiredToken['headers']['status-code']);
+        $this->assertEquals('files', $expiredToken['body']['resourceType']);
+        
+        // Verify that the JWT is generated without causing a 500 error
+        $this->assertNotEmpty($expiredToken['body']['secret']);
+        
+        // Parse the JWT to verify expiration is set correctly for expired tokens
+        $jwtParts = explode('.', $expiredToken['body']['secret']);
+        $this->assertCount(3, $jwtParts, 'JWT should have 3 parts');
+        
+        $payload = json_decode(base64_decode($jwtParts[1]), true);
+        $this->assertArrayHasKey('exp', $payload, 'JWT payload should contain exp field');
+        
+        // For expired tokens, exp should be set to a short time in the future (around 1 minute)
+        $now = time();
+        $this->assertGreaterThan($now, $payload['exp'], 'JWT exp should be in the future even for expired tokens');
+        $this->assertLessThanOrEqual($now + 120, $payload['exp'], 'JWT exp should not be more than 2 minutes in the future for expired tokens');
+
+        return $data;
+    }
+
     /**
      * @depends testCreateToken
      */