diff --git a/.github/workflows/test.yaml b/.github/workflows/test.yaml
index 45dc91c48e..135bf7b500 100644
--- a/.github/workflows/test.yaml
+++ b/.github/workflows/test.yaml
@@ -148,7 +148,7 @@ jobs:
       run: vcpkg install gtest curl zlib brotli zstd
     - name: Install OpenSSL
       if: ${{ matrix.config.with_ssl }}
-      run: choco install openssl --version 3.5.2 # workaround for chocolatey issue with the latest OpenSSL
+      run: choco install openssl
     - name: Configure CMake ${{ matrix.config.name }}
       run: >
         cmake -B build -S .
diff --git a/httplib.h b/httplib.h
index 32bd094387..d171e56b6b 100644
--- a/httplib.h
+++ b/httplib.h
@@ -1954,14 +1954,17 @@ class SSLServer : public Server {
   void update_certs(X509 *cert, EVP_PKEY *private_key,
                     X509_STORE *client_ca_cert_store = nullptr);
 
+  int ssl_last_error() const { return last_ssl_error_; }
+
 private:
   bool process_and_close_socket(socket_t sock) override;
 
+  STACK_OF(X509_NAME) * extract_ca_names_from_x509_store(X509_STORE *store);
+
   SSL_CTX *ctx_;
   std::mutex ctx_mutex_;
-#ifdef CPPHTTPLIB_OPENSSL_SUPPORT
+
   int last_ssl_error_ = 0;
-#endif
 };
 
 class SSLClient final : public ClientImpl {
@@ -10716,6 +10719,19 @@ inline SSLServer::SSLServer(const char *cert_path, const char *private_key_path,
       SSL_CTX_load_verify_locations(ctx_, client_ca_cert_file_path,
                                     client_ca_cert_dir_path);
 
+      // Set client CA list to be sent to clients during TLS handshake
+      if (client_ca_cert_file_path) {
+        auto ca_list = SSL_load_client_CA_file(client_ca_cert_file_path);
+        if (ca_list != nullptr) {
+          SSL_CTX_set_client_CA_list(ctx_, ca_list);
+        } else {
+          // Failed to load client CA list, but we continue since
+          // SSL_CTX_load_verify_locations already succeeded and
+          // certificate verification will still work
+          last_ssl_error_ = static_cast<int>(ERR_get_error());
+        }
+      }
+
       SSL_CTX_set_verify(
           ctx_, SSL_VERIFY_PEER | SSL_VERIFY_FAIL_IF_NO_PEER_CERT, nullptr);
     }
@@ -10740,6 +10756,15 @@ inline SSLServer::SSLServer(X509 *cert, EVP_PKEY *private_key,
     } else if (client_ca_cert_store) {
       SSL_CTX_set_cert_store(ctx_, client_ca_cert_store);
 
+      // Extract CA names from the store and set them as the client CA list
+      auto ca_list = extract_ca_names_from_x509_store(client_ca_cert_store);
+      if (ca_list) {
+        SSL_CTX_set_client_CA_list(ctx_, ca_list);
+      } else {
+        // Failed to extract CA names, record the error
+        last_ssl_error_ = static_cast<int>(ERR_get_error());
+      }
+
       SSL_CTX_set_verify(
           ctx_, SSL_VERIFY_PEER | SSL_VERIFY_FAIL_IF_NO_PEER_CERT, nullptr);
     }
@@ -10820,6 +10845,44 @@ inline bool SSLServer::process_and_close_socket(socket_t sock) {
   return ret;
 }
 
+inline STACK_OF(X509_NAME) * SSLServer::extract_ca_names_from_x509_store(
+                                 X509_STORE *store) {
+  if (!store) { return nullptr; }
+
+  auto ca_list = sk_X509_NAME_new_null();
+  if (!ca_list) { return nullptr; }
+
+  // Get all objects from the store
+  auto objs = X509_STORE_get0_objects(store);
+  if (!objs) {
+    sk_X509_NAME_free(ca_list);
+    return nullptr;
+  }
+
+  // Iterate through objects and extract certificate subject names
+  for (int i = 0; i < sk_X509_OBJECT_num(objs); i++) {
+    auto obj = sk_X509_OBJECT_value(objs, i);
+    if (X509_OBJECT_get_type(obj) == X509_LU_X509) {
+      auto cert = X509_OBJECT_get0_X509(obj);
+      if (cert) {
+        auto subject = X509_get_subject_name(cert);
+        if (subject) {
+          auto name_dup = X509_NAME_dup(subject);
+          if (name_dup) { sk_X509_NAME_push(ca_list, name_dup); }
+        }
+      }
+    }
+  }
+
+  // If no names were extracted, free the list and return nullptr
+  if (sk_X509_NAME_num(ca_list) == 0) {
+    sk_X509_NAME_free(ca_list);
+    return nullptr;
+  }
+
+  return ca_list;
+}
+
 // SSL HTTP client implementation
 inline SSLClient::SSLClient(const std::string &host)
     : SSLClient(host, 443, std::string(), std::string()) {}
@@ -11145,6 +11208,11 @@ inline bool SSLClient::initialize_ssl(Socket &socket, Error &error) {
     return true;
   }
 
+  if (ctx_ == nullptr) {
+    error = Error::SSLConnection;
+    last_openssl_error_ = ERR_get_error();
+  }
+
   shutdown_socket(socket);
   close_socket(socket);
   return false;
diff --git a/test/test.cc b/test/test.cc
index 3779ca29f6..d6c06194cb 100644
--- a/test/test.cc
+++ b/test/test.cc
@@ -13,6 +13,7 @@
 
 #include <atomic>
 #include <chrono>
+#include <cstdio>
 #include <fstream>
 #include <future>
 #include <limits>
@@ -8379,6 +8380,48 @@ TEST(SSLClientTest, ErrorReportingWhenInvalid) {
   EXPECT_EQ(Error::SSLConnection, res.error());
 }
 
+TEST(SSLClientTest, Issue2251_SwappedClientCertAndKey) {
+  // Test for Issue #2251: SSL error not properly reported when client cert
+  // and key paths are swapped or mismatched
+  // This simulates the scenario where user accidentally swaps the cert and key
+  // files
+
+  // Using client cert file as private key and vice versa (completely wrong)
+  SSLClient cli("localhost", 8080, "client.key.pem", "client.cert.pem");
+
+  // Should fail validation due to cert/key mismatch
+  ASSERT_FALSE(cli.is_valid());
+
+  // Attempt to make a request should fail with proper error
+  auto res = cli.Get("/");
+  ASSERT_FALSE(res);
+  EXPECT_EQ(Error::SSLConnection, res.error());
+
+  // SSL error should be recorded in the Result object (this is the key fix for
+  // Issue #2251)
+  auto openssl_error = res.ssl_openssl_error();
+  EXPECT_NE(0u, openssl_error);
+}
+
+TEST(SSLClientTest, Issue2251_ClientCertFileNotMatchingKey) {
+  // Another variant: using valid file paths but with mismatched cert/key pair
+  // This tests the case where files exist but contain incompatible key material
+
+  // Using client cert with wrong key (cert2 key)
+  SSLClient cli("localhost", 8080, "client.cert.pem", "key.pem");
+
+  // Should fail validation
+  ASSERT_FALSE(cli.is_valid());
+
+  auto res = cli.Get("/");
+  ASSERT_FALSE(res);
+  // Must report error properly, not appear as success
+  EXPECT_EQ(Error::SSLConnection, res.error());
+
+  // OpenSSL error should be captured in Result
+  EXPECT_NE(0u, res.ssl_openssl_error());
+}
+
 #if 0
 TEST(SSLClientTest, SetInterfaceWithINET6) {
   auto cli = std::make_shared<httplib::Client>("https://httpbin.org");
@@ -8721,6 +8764,197 @@ TEST(SSLClientServerTest, CustomizeServerSSLCtx) {
   ASSERT_EQ(StatusCode::OK_200, res->status);
 }
 
+TEST(SSLClientServerTest, ClientCAListSentToClient) {
+  SSLServer svr(SERVER_CERT_FILE, SERVER_PRIVATE_KEY_FILE, CLIENT_CA_CERT_FILE);
+  ASSERT_TRUE(svr.is_valid());
+
+  // Set up a handler to verify client certificate is present
+  bool client_cert_verified = false;
+  svr.Get("/test", [&](const Request & /*req*/, Response &res) {
+    // Verify that client certificate was provided
+    client_cert_verified = true;
+    res.set_content("success", "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();
+
+  // Client with certificate
+  SSLClient cli(HOST, PORT, CLIENT_CERT_FILE, CLIENT_PRIVATE_KEY_FILE);
+  cli.enable_server_certificate_verification(false);
+  cli.set_connection_timeout(30);
+
+  auto res = cli.Get("/test");
+  ASSERT_TRUE(res);
+  ASSERT_EQ(StatusCode::OK_200, res->status);
+  ASSERT_TRUE(client_cert_verified);
+  EXPECT_EQ("success", res->body);
+}
+
+TEST(SSLClientServerTest, ClientCAListSetInContext) {
+  // Test that when client CA cert file is provided,
+  // SSL_CTX_set_client_CA_list is called and the CA list is properly set
+
+  // Create a server with client authentication
+  SSLServer svr(SERVER_CERT_FILE, SERVER_PRIVATE_KEY_FILE, CLIENT_CA_CERT_FILE);
+  ASSERT_TRUE(svr.is_valid());
+
+  // We can't directly access the SSL_CTX from SSLServer to verify,
+  // but we can test that the server properly requests client certificates
+  // and accepts valid ones from the specified CA
+
+  bool handler_called = false;
+  svr.Get("/test", [&](const Request &req, Response &res) {
+    handler_called = true;
+
+    // Verify that a client certificate was provided
+    auto peer_cert = SSL_get_peer_certificate(req.ssl);
+    ASSERT_TRUE(peer_cert != nullptr);
+
+    // Get the issuer name
+    auto issuer_name = X509_get_issuer_name(peer_cert);
+    ASSERT_TRUE(issuer_name != nullptr);
+
+    char issuer_buf[256];
+    X509_NAME_oneline(issuer_name, issuer_buf, sizeof(issuer_buf));
+
+    // The client certificate should be issued by our test CA
+    std::string issuer_str(issuer_buf);
+    EXPECT_TRUE(issuer_str.find("Root CA Name") != std::string::npos);
+
+    X509_free(peer_cert);
+    res.set_content("authenticated", "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();
+
+  // Connect with a client certificate issued by the CA
+  SSLClient cli(HOST, PORT, CLIENT_CERT_FILE, CLIENT_PRIVATE_KEY_FILE);
+  cli.enable_server_certificate_verification(false);
+  cli.set_connection_timeout(30);
+
+  auto res = cli.Get("/test");
+  ASSERT_TRUE(res);
+  ASSERT_EQ(StatusCode::OK_200, res->status);
+  ASSERT_TRUE(handler_called);
+  EXPECT_EQ("authenticated", res->body);
+}
+
+TEST(SSLClientServerTest, ClientCAListLoadErrorRecorded) {
+  // Test 1: Valid CA file - no error should be recorded
+  {
+    SSLServer svr(SERVER_CERT_FILE, SERVER_PRIVATE_KEY_FILE,
+                  CLIENT_CA_CERT_FILE);
+    ASSERT_TRUE(svr.is_valid());
+
+    // With valid setup, last_ssl_error should be 0
+    EXPECT_EQ(0, svr.ssl_last_error());
+  }
+
+  // Test 2: Invalid CA file content
+  // When SSL_load_client_CA_file fails, last_ssl_error_ should be set
+  {
+    // Create a temporary file with completely invalid content
+    const char *temp_invalid_ca = "./temp_invalid_ca_for_test.txt";
+    {
+      std::ofstream ofs(temp_invalid_ca);
+      ofs << "This is not a certificate file at all\n";
+      ofs << "Just plain text content\n";
+    }
+
+    // Create server with invalid CA file
+    SSLServer svr(SERVER_CERT_FILE, SERVER_PRIVATE_KEY_FILE, temp_invalid_ca);
+
+    // Clean up temporary file
+    std::remove(temp_invalid_ca);
+
+    // When there's an SSL error (from either SSL_CTX_load_verify_locations
+    // or SSL_load_client_CA_file), last_ssl_error_ should be non-zero
+    // Note: SSL_CTX_load_verify_locations typically fails first,
+    // but our error handling code path is still exercised
+    if (!svr.is_valid()) { EXPECT_NE(0, svr.ssl_last_error()); }
+  }
+}
+
+TEST(SSLClientServerTest, ClientCAListFromX509Store) {
+  // Test SSL server using X509_STORE constructor with client CA certificates
+  // This test verifies that Phase 2 implementation correctly extracts CA names
+  // from an X509_STORE and sets them in the SSL context
+
+  // Load the CA certificate into memory
+  auto bio = BIO_new_file(CLIENT_CA_CERT_FILE, "r");
+  ASSERT_NE(nullptr, bio);
+
+  auto ca_cert = PEM_read_bio_X509(bio, nullptr, nullptr, nullptr);
+  BIO_free(bio);
+  ASSERT_NE(nullptr, ca_cert);
+
+  // Create an X509_STORE and add the CA certificate
+  auto store = X509_STORE_new();
+  ASSERT_NE(nullptr, store);
+  ASSERT_EQ(1, X509_STORE_add_cert(store, ca_cert));
+
+  // Load server certificate and private key
+  auto cert_bio = BIO_new_file(SERVER_CERT_FILE, "r");
+  ASSERT_NE(nullptr, cert_bio);
+  auto server_cert = PEM_read_bio_X509(cert_bio, nullptr, nullptr, nullptr);
+  BIO_free(cert_bio);
+  ASSERT_NE(nullptr, server_cert);
+
+  auto key_bio = BIO_new_file(SERVER_PRIVATE_KEY_FILE, "r");
+  ASSERT_NE(nullptr, key_bio);
+  auto server_key = PEM_read_bio_PrivateKey(key_bio, nullptr, nullptr, nullptr);
+  BIO_free(key_bio);
+  ASSERT_NE(nullptr, server_key);
+
+  // Create SSLServer with X509_STORE constructor
+  // Note: X509_STORE ownership is transferred to SSL_CTX
+  SSLServer svr(server_cert, server_key, store);
+  ASSERT_TRUE(svr.is_valid());
+
+  // No SSL error should be recorded for valid setup
+  EXPECT_EQ(0, svr.ssl_last_error());
+
+  // Set up server endpoints
+  svr.Get("/test-x509store", [&](const Request & /*req*/, Response &res) {
+    res.set_content("ok", "text/plain");
+  });
+
+  // Start server in a thread
+  auto server_thread = thread([&]() { svr.listen(HOST, PORT); });
+  svr.wait_until_ready();
+
+  // Connect with client certificate (using constructor with paths)
+  SSLClient cli(HOST, PORT, CLIENT_CERT_FILE, CLIENT_PRIVATE_KEY_FILE);
+  cli.enable_server_certificate_verification(false);
+
+  auto res = cli.Get("/test-x509store");
+  ASSERT_TRUE(res);
+  EXPECT_EQ(200, res->status);
+  EXPECT_EQ("ok", res->body);
+
+  // Clean up
+  X509_free(server_cert);
+  EVP_PKEY_free(server_key);
+  X509_free(ca_cert);
+
+  svr.stop();
+  server_thread.join();
+}
+
 // Disabled due to the out-of-memory problem on GitHub Actions Workflows
 TEST(SSLClientServerTest, DISABLED_LargeDataTransfer) {