diff --git a/httplib.h b/httplib.h
index e7d2f176a1..eccfb2bcb1 100644
--- a/httplib.h
+++ b/httplib.h
@@ -10698,10 +10698,9 @@ inline bool match_hostname(const std::string &pattern,
 // Verify certificate using Windows CertGetCertificateChain API.
 // This provides real-time certificate validation with Windows Update
 // integration, independent of the TLS backend (OpenSSL or MbedTLS).
-inline bool
-verify_cert_with_windows_schannel(const std::vector<unsigned char> &der_cert,
-                                  const std::string &hostname,
-                                  bool verify_hostname, uint64_t &out_error) {
+inline bool verify_cert_with_windows_schannel(
+    const std::vector<unsigned char> &der_cert, const std::string &hostname,
+    bool verify_hostname, uint64_t &out_error, tls::const_session_t session) {
   if (der_cert.empty()) { return false; }
 
   out_error = 0;
@@ -10719,14 +10718,35 @@ verify_cert_with_windows_schannel(const std::vector<unsigned char> &der_cert,
   auto cert_guard =
       scope_exit([&] { CertFreeCertificateContext(cert_context); });
 
-  // Setup chain parameters
+#ifdef CPPHTTPLIB_OPENSSL_SUPPORT
+  // Add the intermediates the server sent. Without them CryptoAPI follows the
+  // leaf's AIA URL, which may lead to an issuer under an untrusted root.
+  auto store = CertOpenStore(CERT_STORE_PROV_MEMORY, 0, 0, 0, nullptr);
+  auto store_guard = scope_exit([&] { CertCloseStore(store, 0); });
+  auto sk = SSL_get_peer_cert_chain(static_cast<const SSL *>(session));
+  for (int i = 1; sk && i < sk_X509_num(sk); i++) {
+    std::vector<unsigned char> der;
+    tls::get_cert_der(sk_X509_value(sk, i), der);
+    CertAddEncodedCertificateToStore(store, X509_ASN_ENCODING, der.data(),
+                                     static_cast<DWORD>(der.size()),
+                                     CERT_STORE_ADD_USE_EXISTING, nullptr);
+  }
+#else
+  (void)session;
+  auto store = cert_context->hCertStore;
+#endif
+
+  // Setup chain parameters. The SSL policy does not check the key usage.
+  LPSTR server_auth = const_cast<LPSTR>(szOID_PKIX_KP_SERVER_AUTH);
   CERT_CHAIN_PARA chain_para = {};
   chain_para.cbSize = sizeof(chain_para);
+  chain_para.RequestedUsage.Usage.cUsageIdentifier = 1;
+  chain_para.RequestedUsage.Usage.rgpszUsageIdentifier = &server_auth;
 
   // Build certificate chain with revocation checking
   PCCERT_CHAIN_CONTEXT chain_context = nullptr;
   auto chain_result = CertGetCertificateChain(
-      nullptr, cert_context, nullptr, cert_context->hCertStore, &chain_para,
+      nullptr, cert_context, nullptr, store, &chain_para,
       CERT_CHAIN_CACHE_END_CERT | CERT_CHAIN_REVOCATION_CHECK_END_CERT |
           CERT_CHAIN_REVOCATION_ACCUMULATIVE_TIMEOUT,
       nullptr, &chain_context);
@@ -10919,6 +10939,15 @@ inline bool setup_client_tls_session(
   if (verification_status == SSLVerifierResponse::NoDecisionMade &&
       server_certificate_verification) {
     auto verify_result = get_verify_result(session);
+#if defined(CPPHTTPLIB_WINDOWS_AUTOMATIC_ROOT_CERTIFICATES_UPDATE) &&          \
+    defined(CPPHTTPLIB_OPENSSL_SUPPORT)
+    // Windows adds a root it trusts to its store only when CryptoAPI needs it,
+    // so leave a root missing from the store to the CryptoAPI check below
+    if (options.windows_cert_verification &&
+        verify_result == X509_V_ERR_UNABLE_TO_GET_ISSUER_CERT_LOCALLY) {
+      verify_result = X509_V_OK;
+    }
+#endif
     if (verify_result != 0) {
       return fail(Error::SSLServerVerification, 0,
                   static_cast<uint64_t>(verify_result));
@@ -10949,10 +10978,12 @@ inline bool setup_client_tls_session(
       if (get_cert_der(server_cert, der)) {
         uint64_t wincrypt_error = 0;
         if (!verify_cert_with_windows_schannel(
-                der, host, options.server_hostname_verification,
-                wincrypt_error)) {
+                der, host, options.server_hostname_verification, wincrypt_error,
+                session)) {
           return fail(Error::SSLServerVerification, 0, wincrypt_error);
         }
+      } else {
+        return fail(Error::SSLServerVerification, 0, get_error());
       }
     }
 #endif
diff --git a/test/test.cc b/test/test.cc
index f7383094a0..5fa11ca16e 100644
--- a/test/test.cc
+++ b/test/test.cc
@@ -13958,6 +13958,43 @@ TEST(SSLClientTest, WindowsCertificateVerification_Disabled) {
   auto res = cli.Get("/");
   if (res) { EXPECT_NE(StatusCode::InternalServerError_500, res->status); }
 }
+
+// The server sends an intermediate cross-signed by a root Windows trusts,
+// while the leaf's AIA URL leads to one under a root Windows does not trust.
+TEST(SSLClientTest, WindowsCertificateVerification_ServerIntermediates_Online) {
+  SSLClient cli("accounts.spotify.com", 443);
+  auto res = cli.Get("/");
+  ASSERT_TRUE(res) << "Error: " << to_string(res.error())
+                   << " ssl_backend_error=" << res.ssl_backend_error();
+}
+
+// A root missing from the trust store is left to CryptoAPI, which must still
+// reject a chain whose root Windows does not trust either.
+TEST(SSLClientTest, WindowsCertificateVerification_UnknownIssuerRejected) {
+  // Issued by the test root CA, which is not in the Windows root store
+  SSLServer svr(CLIENT_CERT_FILE, CLIENT_PRIVATE_KEY_FILE);
+  ASSERT_TRUE(svr.is_valid());
+  svr.Get("/", [](const Request &, Response &res) {
+    res.set_content("ok", "text/plain");
+  });
+
+  thread t = thread([&]() { ASSERT_TRUE(svr.listen(HOST, PORT)); });
+  auto se = detail::scope_exit([&] {
+    svr.stop();
+    t.join();
+    ASSERT_FALSE(svr.is_running());
+  });
+
+  svr.wait_until_ready();
+
+  SSLClient cli(HOST, PORT);
+  // Keep the hostname check from failing first
+  cli.enable_server_hostname_verification(false);
+
+  auto res = cli.Get("/");
+  ASSERT_FALSE(res);
+  EXPECT_EQ(Error::SSLServerVerification, res.error());
+}
 #endif
 
 TEST(SSLClientTest, ServerCertificateVerification1_Online) {