diff --git a/.changeset/fix-multiple-token-types-array.md b/.changeset/fix-multiple-token-types-array.md
new file mode 100644
index 00000000000..db48bdbb5db
--- /dev/null
+++ b/.changeset/fix-multiple-token-types-array.md
@@ -0,0 +1,5 @@
+---
+"@clerk/backend": patch
+---
+
+Fix token-type-mismatch error when using multiple `acceptsToken` values in `authenticateRequest`. When `acceptsToken` is an array containing both session and machine token types (e.g., `['session_token', 'api_key']`), the function now correctly routes to the appropriate authentication handler based on the actual token type, instead of always treating them as machine tokens.
\ No newline at end of file
diff --git a/packages/backend/src/tokens/__tests__/request.test.ts b/packages/backend/src/tokens/__tests__/request.test.ts
index 0d140f8b093..54b2e775e01 100644
--- a/packages/backend/src/tokens/__tests__/request.test.ts
+++ b/packages/backend/src/tokens/__tests__/request.test.ts
@@ -1426,6 +1426,38 @@ describe('tokens.authenticateRequest(options)', () => {
           isAuthenticated: false,
         });
       });
+
+      test('accepts session_token when it is in acceptsToken array with machine tokens', async () => {
+        server.use(
+          http.get('https://api.clerk.test/v1/jwks', () => {
+            return HttpResponse.json(mockJwks);
+          }),
+        );
+
+        const request = mockRequest({ authorization: `Bearer ${mockJwt}` });
+        const requestState = await authenticateRequest(
+          request,
+          mockOptions({ acceptsToken: ['session_token', 'api_key'] }),
+        );
+
+        expect(requestState).toBeSignedIn();
+      });
+
+      test('accepts api_key when it is in acceptsToken array with session_token', async () => {
+        server.use(
+          http.post(mockMachineAuthResponses.api_key.endpoint, () => {
+            return HttpResponse.json(mockVerificationResults.api_key);
+          }),
+        );
+
+        const request = mockRequest({ authorization: `Bearer ${mockTokens.api_key}` });
+        const requestState = await authenticateRequest(
+          request,
+          mockOptions({ acceptsToken: ['session_token', 'api_key'] }),
+        );
+
+        expect(requestState).toBeMachineAuthenticated();
+      });
     });
 
     describe('Token Location Validation', () => {
diff --git a/packages/backend/src/tokens/request.ts b/packages/backend/src/tokens/request.ts
index 0061828b026..6624c292205 100644
--- a/packages/backend/src/tokens/request.ts
+++ b/packages/backend/src/tokens/request.ts
@@ -788,6 +788,13 @@ export const authenticateRequest: AuthenticateRequest = (async (
     if (acceptsToken === TokenType.SessionToken) {
       return authenticateRequestWithTokenInHeader();
     }
+    // When acceptsToken is an array, route based on the actual token type
+    if (Array.isArray(acceptsToken)) {
+      if (isMachineToken(authenticateContext.tokenInHeader)) {
+        return authenticateMachineRequestWithTokenInHeader();
+      }
+      return authenticateRequestWithTokenInHeader();
+    }
     return authenticateMachineRequestWithTokenInHeader();
   }