diff --git a/ProcessMaker/Http/Middleware/ProcessMakerAuthenticate.php b/ProcessMaker/Http/Middleware/ProcessMakerAuthenticate.php
index b64c13812e..283f9b4c16 100644
--- a/ProcessMaker/Http/Middleware/ProcessMakerAuthenticate.php
+++ b/ProcessMaker/Http/Middleware/ProcessMakerAuthenticate.php
@@ -3,8 +3,11 @@
 namespace ProcessMaker\Http\Middleware;
 
 use Closure;
+use Illuminate\Auth\AuthenticationException;
 use Illuminate\Auth\Middleware\Authenticate;
 use Illuminate\Support\Str;
+use League\OAuth2\Server\Exception\OAuthServerException;
+use ProcessMaker\Services\InvalidBearerTokenCache;
 
 class ProcessMakerAuthenticate extends Authenticate
 {
@@ -29,7 +32,8 @@ protected function authenticate($request, array $guards)
     {
         $this->addAcceptJsonHeaderIfApiCall($request, $guards);
 
-        // Load permissions into the session
+        InvalidBearerTokenCache::prepareApiBearerBeforePassport($request, $guards);
+
         if (auth()->check() && !$request->ajax()) {
             $permissions = $request->user()->loadPermissions();
             session(['permissions' => $permissions]);
@@ -39,9 +43,15 @@ protected function authenticate($request, array $guards)
     }
 
     /**
-     * @param array $guards
-     * @param \Illuminate\Http\Request $request
+     * {@inheritdoc}
      */
+    protected function unauthenticated($request, array $guards)
+    {
+        InvalidBearerTokenCache::rememberPassportJwtFailure($request, $guards);
+
+        throw new AuthenticationException('Unauthenticated.', $guards);
+    }
+
     private function addAcceptJsonHeaderIfApiCall(\Illuminate\Http\Request $request, array $guards): void
     {
         if (in_array('api', $guards) && !$this->requestHasAcceptJsonHeader($request)) {
@@ -49,10 +59,6 @@ private function addAcceptJsonHeaderIfApiCall(\Illuminate\Http\Request $request,
         }
     }
 
-    /**
-     * @param \Illuminate\Http\Request $request
-     * @return bool
-     */
     private function requestHasAcceptJsonHeader(\Illuminate\Http\Request $request): bool
     {
         return Str::contains($request->header('accept'), ['/json', '+json']);
diff --git a/ProcessMaker/Services/InvalidBearerTokenCache.php b/ProcessMaker/Services/InvalidBearerTokenCache.php
new file mode 100644
index 0000000000..b18bec808c
--- /dev/null
+++ b/ProcessMaker/Services/InvalidBearerTokenCache.php
@@ -0,0 +1,153 @@
+<?php
+
+namespace ProcessMaker\Services;
+
+use Illuminate\Auth\AuthenticationException;
+use Illuminate\Cache\Repository;
+use Illuminate\Contracts\Cache\Repository as RepositoryContract;
+use Illuminate\Http\Request;
+use Illuminate\Support\Facades\Cache;
+
+class InvalidBearerTokenCache
+{
+    private const CACHE_PREFIX = 'invalid_bearer:';
+
+    private const ATTR_STASHED_JWT = 'pm_invalid_bearer_token_record';
+
+    private const ATTR_ALREADY_CACHED = 'pm_invalid_bearer_failure_recorded';
+
+    private static ?RepositoryContract $repositoryForTesting = null;
+
+    private static ?int $ttlSecondsForTesting = null;
+
+    public static function prepareApiBearerBeforePassport(Request $request, array $guards): void
+    {
+        if (!self::isApiBearerRequest($request, $guards)) {
+            return;
+        }
+
+        $jwt = self::jwtBearerFromRequest($request);
+        if ($jwt !== null && self::isInNegativeCache($jwt)) {
+            throw new AuthenticationException('Unauthenticated.', $guards);
+        }
+
+        $rawBearer = self::bearerFromAuthorizationHeader($request);
+        if ($rawBearer !== null && !self::looksLikeJwt($rawBearer)) {
+            throw new AuthenticationException('Unauthenticated.', $guards);
+        }
+
+        if ($rawBearer !== null && self::looksLikeJwt($rawBearer)) {
+            $request->attributes->set(self::ATTR_STASHED_JWT, $rawBearer);
+        }
+    }
+
+    public static function rememberPassportJwtFailure(Request $request, array $guards = []): void
+    {
+        if (!self::isApiBearerRequest($request, $guards)) {
+            return;
+        }
+
+        $jwt = self::jwtBearerFromRequest($request);
+        if ($jwt === null || self::ttlSeconds() <= 0) {
+            return;
+        }
+
+        if ($request->attributes->get(self::ATTR_ALREADY_CACHED)) {
+            return;
+        }
+
+        self::cache()->put(self::cacheKey($jwt), true, self::ttlSeconds());
+        $request->attributes->set(self::ATTR_ALREADY_CACHED, true);
+    }
+
+    public static function isInNegativeCache(string $token): bool
+    {
+        if (self::ttlSeconds() <= 0) {
+            return false;
+        }
+
+        return self::cache()->has(self::cacheKey($token));
+    }
+
+    public static function setRepositoryForTesting(?RepositoryContract $repository): void
+    {
+        self::$repositoryForTesting = $repository;
+    }
+
+    public static function setTtlSecondsForTesting(?int $ttl): void
+    {
+        self::$ttlSecondsForTesting = $ttl;
+    }
+
+    private static function isApiBearerRequest(Request $request, array $guards): bool
+    {
+        if ($guards !== [] && !in_array('api', $guards, true)) {
+            return false;
+        }
+
+        if ($guards === [] && !str_starts_with($request->path(), 'api/')) {
+            return false;
+        }
+
+        return self::bearerFromAuthorizationHeader($request) !== null
+            || $request->attributes->has(self::ATTR_STASHED_JWT);
+    }
+
+    private static function jwtBearerFromRequest(Request $request): ?string
+    {
+        $fromHeader = self::bearerFromAuthorizationHeader($request);
+        if ($fromHeader !== null && self::looksLikeJwt($fromHeader)) {
+            return $fromHeader;
+        }
+
+        $stashed = $request->attributes->get(self::ATTR_STASHED_JWT);
+        if (is_string($stashed) && self::looksLikeJwt($stashed)) {
+            return $stashed;
+        }
+
+        return null;
+    }
+
+    private static function bearerFromAuthorizationHeader(Request $request): ?string
+    {
+        $header = $request->header('Authorization', '');
+        if (!str_starts_with($header, 'Bearer ')) {
+            return null;
+        }
+
+        $token = trim(substr($header, 7));
+
+        return $token === '' ? null : $token;
+    }
+
+    private static function looksLikeJwt(string $token): bool
+    {
+        return substr_count($token, '.') === 2;
+    }
+
+    private static function cacheKey(string $token): string
+    {
+        return self::CACHE_PREFIX . hash('sha256', $token);
+    }
+
+    private static function ttlSeconds(): int
+    {
+        if (self::$ttlSecondsForTesting !== null) {
+            return self::$ttlSecondsForTesting;
+        }
+
+        return (int) config('auth.invalid_bearer_cache_ttl', 60);
+    }
+
+    private static function cache(): RepositoryContract
+    {
+        if (self::$repositoryForTesting !== null) {
+            return self::$repositoryForTesting;
+        }
+
+        /** @var Repository $store */
+        $store = Cache::store();
+
+        return $store;
+    }
+}
diff --git a/config/auth.php b/config/auth.php
index e7811a250d..7b34bcec1d 100644
--- a/config/auth.php
+++ b/config/auth.php
@@ -111,6 +111,12 @@
 
     'log_auth_events' => env('LOG_AUTH_EVENTS', true),
 
+    /*
+    | Seconds to cache a failed JWT-shaped Bearer (hash only) so repeat requests skip Passport.
+    | Set AUTH_INVALID_BEARER_CACHE_TTL=0 to disable.
+    */
+    'invalid_bearer_cache_ttl' => (int) env('AUTH_INVALID_BEARER_CACHE_TTL', 60),
+
     /*
     |--------------------------------------------------------------------------
     | Password Confirmation Timeout
diff --git a/tests/Feature/Http/Middleware/ProcessMakerAuthenticateInvalidBearerTest.php b/tests/Feature/Http/Middleware/ProcessMakerAuthenticateInvalidBearerTest.php
new file mode 100644
index 0000000000..6066e40e5c
--- /dev/null
+++ b/tests/Feature/Http/Middleware/ProcessMakerAuthenticateInvalidBearerTest.php
@@ -0,0 +1,55 @@
+<?php
+
+namespace Tests\Feature\Http\Middleware;
+
+use Illuminate\Cache\ArrayStore;
+use Illuminate\Cache\Repository;
+use Illuminate\Http\Request;
+use ProcessMaker\Services\InvalidBearerTokenCache;
+use Tests\TestCase;
+
+class ProcessMakerAuthenticateInvalidBearerTest extends TestCase
+{
+    protected function setUp(): void
+    {
+        parent::setUp();
+
+        InvalidBearerTokenCache::setRepositoryForTesting(new Repository(new ArrayStore()));
+        InvalidBearerTokenCache::setTtlSecondsForTesting(60);
+    }
+
+    protected function tearDown(): void
+    {
+        InvalidBearerTokenCache::setRepositoryForTesting(null);
+        InvalidBearerTokenCache::setTtlSecondsForTesting(null);
+
+        parent::tearDown();
+    }
+
+    public function testNonJwtBearerWithoutAcceptJsonReturns401(): void
+    {
+        $response = $this->withHeaders([
+            'Authorization' => 'Bearer FAKE_JWT',
+            'Accept' => 'text/html',
+        ])->get('/api/1.0/tasks');
+
+        $response->assertStatus(401);
+        $response->assertJson(['error' => 'Unauthenticated.']);
+    }
+
+    public function testCachedInvalidJwtWithoutAcceptJsonReturns401(): void
+    {
+        $token = 'aaa.bbb.ccc';
+        $request = Request::create('/api/1.0/tasks', 'GET');
+        $request->headers->set('Authorization', 'Bearer ' . $token);
+        InvalidBearerTokenCache::rememberPassportJwtFailure($request, ['api']);
+
+        $response = $this->withHeaders([
+            'Authorization' => 'Bearer ' . $token,
+            'Accept' => 'text/html',
+        ])->get('/api/1.0/tasks');
+
+        $response->assertStatus(401);
+        $response->assertJson(['error' => 'Unauthenticated.']);
+    }
+}
diff --git a/tests/unit/ProcessMaker/Services/InvalidBearerTokenCacheTest.php b/tests/unit/ProcessMaker/Services/InvalidBearerTokenCacheTest.php
new file mode 100644
index 0000000000..4a3a41a861
--- /dev/null
+++ b/tests/unit/ProcessMaker/Services/InvalidBearerTokenCacheTest.php
@@ -0,0 +1,156 @@
+<?php
+
+namespace Tests\Unit\ProcessMaker\Services;
+
+use Illuminate\Auth\AuthenticationException;
+use Illuminate\Cache\ArrayStore;
+use Illuminate\Cache\Repository;
+use Illuminate\Http\Request;
+use PHPUnit\Framework\TestCase;
+use ProcessMaker\Services\InvalidBearerTokenCache;
+
+class InvalidBearerTokenCacheTest extends TestCase
+{
+    private Repository $cache;
+
+    protected function setUp(): void
+    {
+        parent::setUp();
+        $this->cache = new Repository(new ArrayStore());
+        InvalidBearerTokenCache::setRepositoryForTesting($this->cache);
+        InvalidBearerTokenCache::setTtlSecondsForTesting(60);
+    }
+
+    protected function tearDown(): void
+    {
+        InvalidBearerTokenCache::setRepositoryForTesting(null);
+        InvalidBearerTokenCache::setTtlSecondsForTesting(null);
+        parent::tearDown();
+    }
+
+    public function testRememberPassportJwtFailureMarksTokenForSkipPassport(): void
+    {
+        $token = 'aaa.bbb.ccc';
+        $request = Request::create('/api/1.0/tasks', 'GET');
+        $request->headers->set('Authorization', 'Bearer ' . $token);
+
+        $this->assertFalse(InvalidBearerTokenCache::isInNegativeCache($token));
+
+        InvalidBearerTokenCache::rememberPassportJwtFailure($request, ['api']);
+
+        $this->assertTrue(InvalidBearerTokenCache::isInNegativeCache($token));
+    }
+
+    public function testPrepareApiBearerBeforePassportThrowsWhenTokenWasCached(): void
+    {
+        $request = Request::create('/api/1.0/tasks', 'GET');
+        $request->headers->set('Authorization', 'Bearer aaa.bbb.ccc');
+
+        InvalidBearerTokenCache::rememberPassportJwtFailure($request, ['api']);
+
+        $this->expectException(AuthenticationException::class);
+
+        InvalidBearerTokenCache::prepareApiBearerBeforePassport($request, ['api']);
+    }
+
+    public function testPrepareApiBearerBeforePassportRejectsBearerWithoutJwtShape(): void
+    {
+        $request = $this->requestWithAuthorization('Bearer FAKE_JWT');
+
+        $this->expectException(AuthenticationException::class);
+
+        InvalidBearerTokenCache::prepareApiBearerBeforePassport($request, ['api']);
+    }
+
+    public function testPrepareApiBearerBeforePassportAllowsJwtShapedBearerThrough(): void
+    {
+        $request = $this->requestWithAuthorization('Bearer aaa.bbb.ccc');
+
+        InvalidBearerTokenCache::prepareApiBearerBeforePassport($request, ['api']);
+        $this->addToAssertionCount(1);
+    }
+
+    public function testPrepareApiBearerBeforePassportIgnoresEmptyBearer(): void
+    {
+        InvalidBearerTokenCache::prepareApiBearerBeforePassport(
+            $this->requestWithAuthorization('Bearer '),
+            ['api']
+        );
+        $this->addToAssertionCount(1);
+    }
+
+    public function testPrepareApiBearerBeforePassportIgnoresWhitespaceOnlyBearer(): void
+    {
+        InvalidBearerTokenCache::prepareApiBearerBeforePassport(
+            $this->requestWithAuthorization('Bearer    '),
+            ['api']
+        );
+        $this->addToAssertionCount(1);
+    }
+
+    public function testPrepareApiBearerBeforePassportAppliesWhenApiGuardAmongMultiple(): void
+    {
+        InvalidBearerTokenCache::prepareApiBearerBeforePassport(
+            $this->requestWithAuthorization('Bearer aaa.bbb.ccc'),
+            ['web', 'api']
+        );
+        $this->addToAssertionCount(1);
+    }
+
+    public function testPrepareApiBearerBeforePassportSkipsNonApiGuard(): void
+    {
+        InvalidBearerTokenCache::prepareApiBearerBeforePassport(
+            $this->requestWithAuthorization('Bearer FAKE_JWT'),
+            ['web']
+        );
+        $this->addToAssertionCount(1);
+    }
+
+    public function testPrepareApiBearerBeforePassportSkipsWithoutBearerHeader(): void
+    {
+        InvalidBearerTokenCache::prepareApiBearerBeforePassport(
+            Request::create('/api/1.0/tasks', 'GET'),
+            ['api']
+        );
+        $this->addToAssertionCount(1);
+    }
+
+    public function testPrepareApiBearerBeforePassportSkipsNonBearerScheme(): void
+    {
+        InvalidBearerTokenCache::prepareApiBearerBeforePassport(
+            $this->requestWithAuthorization('Basic dXNlcjpwYXNz'),
+            ['api']
+        );
+        $this->addToAssertionCount(1);
+    }
+
+    public function testDoesNotCacheMalformedTokensFromRequest(): void
+    {
+        $request = Request::create('/api/1.0/tasks', 'GET');
+        $request->headers->set('Authorization', 'Bearer FAKE_JWT');
+
+        InvalidBearerTokenCache::rememberPassportJwtFailure($request, ['api']);
+
+        $this->assertFalse(InvalidBearerTokenCache::isInNegativeCache('FAKE_JWT'));
+    }
+
+    public function testRememberPassportJwtFailureUsesStashedTokenAfterPassportClearsHeader(): void
+    {
+        $request = Request::create('/api/1.0/tasks', 'GET');
+        $request->headers->set('Authorization', 'Bearer aaa.bbb.ccc');
+        InvalidBearerTokenCache::prepareApiBearerBeforePassport($request, ['api']);
+        $request->headers->remove('Authorization');
+
+        InvalidBearerTokenCache::rememberPassportJwtFailure($request, ['api']);
+
+        $this->assertTrue(InvalidBearerTokenCache::isInNegativeCache('aaa.bbb.ccc'));
+    }
+
+    private function requestWithAuthorization(string $authorization): Request
+    {
+        $request = Request::create('/api/1.0/tasks', 'GET');
+        $request->headers->set('Authorization', $authorization);
+
+        return $request;
+    }
+}