test: socket error handling in HTTPServer using ErrorSock mock socket

diff --git a/src/test/httpserver_tests.cpp b/src/test/httpserver_tests.cpp
index 33c8b776..8e66d3d4 100644
--- a/src/test/httpserver_tests.cpp
+++ b/src/test/httpserver_tests.cpp
@@ -5,6 +5,7 @@
 #include <httpserver.h>
 #include <rpc/protocol.h>
 #include <test/util/common.h>
+#include <test/util/logging.h>
 #include <test/util/setup_common.h>
 #include <util/string.h>
 
@@ -628,4 +629,122 @@ BOOST_AUTO_TEST_CASE(http_server_socket_tests)
     server.StopListening();
 }
 
+BOOST_AUTO_TEST_CASE(http_socket_error_tests)
+{
+    // Hard-code the server's request handler to respond to each request with
+    // an incremented block count.
+    int height{0};
+    HTTPServer server{[&](std::shared_ptr<HTTPRequest> req) {
+        req->WriteReply(HTTP_OK, strprintf("height: %d\n", height++));
+    }};
+
+    // All replies will be the same size
+    static constexpr std::size_t reply_length = std::string_view{
+        "HTTP/1.1 200 OK\r\n"
+        "Date: Thu, 01 Jan 2026 00:00:00 GMT\r\n"           // All RFC1123 dates are 29 characters
+        "Content-Length: 10\r\n"
+        "Content-Type: text/html; charset=ISO-8859-1\r\n"
+        "\r\n"
+        "height: 0\n"
+    }.size();
+
+    /**
+     * A mocked Sock derived from DynSock whose Send() only succeeds when there is more than
+     * one reply being sent (send buffer length > reply_length). Otherwise it returns
+     * a recoverable error (WSAEAGAIN).
+     *
+     * After it sends successfully once, it continues to always succeed.
+     *
+     * Useful for testing "try again" logic around non-blocking socket Send() failures.
+     */
+    class ErrorSock : public DynSock
+    {
+    public:
+        explicit ErrorSock(std::shared_ptr<Pipes> pipes) : DynSock{std::move(pipes)} {}
+        DynSock& operator=(Sock&&) override { assert(false); return *this; }
+
+        ssize_t Send(const void* buf, size_t len, int flags) const override
+        {
+            if (len <= reply_length && !m_have_sent) {
+                #ifdef WIN32
+                WSASetLastError(WSAEWOULDBLOCK);
+                #else
+                errno = WSAEAGAIN;
+                #endif
+                return -1;
+            } else {
+                m_have_sent = true;
+                return DynSock::Send(buf, len, flags);
+            }
+        }
+
+        mutable bool m_have_sent{false};
+    };
+
+    // Simpler server startup than the last test
+    CService addr_bind{Lookup("0.0.0.0", /*portDefault=*/0, /*fAllowLookup=*/false).value()};
+    BOOST_REQUIRE(server.BindAndStartListening(addr_bind));
+    server.StartSocketsThreads();
+
+    // Prepare initial requests
+    int num_requests = 3;
+    // Use keep-alive so the server holds the connection open for all requests.
+    std::string keepalive_request{full_request};
+    keepalive_request.replace(keepalive_request.find("Connection: close"), 17, "Connection: keep-alive");
+    // Combine all requests so they are read from the socket on a single iteration of the I/O loop
+    std::string all_requests;
+    for (int i = 0; i < num_requests; i++) {
+        all_requests += keepalive_request;
+    }
+
+    // Watch the log messages to ensure that the first two replies were sent
+    // together. This indicates the non-optimistic send path was used
+    // because a reply was already sitting in the send buffer when a second reply
+    // was added.
+    DebugLogHelper find_two_replies{strprintf("Sent %d bytes to client", reply_length * 2),
+                                    [&](const std::string* s) {
+                                        return true;
+                                    }};
+    // Last reply should be sent on its own by optimistic send path, because
+    // the send buffer was empty when the reply was written.
+    DebugLogHelper find_one_reply{strprintf("Sent %d bytes to client", reply_length),
+                                  [&](const std::string* s) {
+                                      return true;
+                                   }};
+
+    // Connect the ErrorSock as mock client with the preloaded data and get a handle on the I/O pipes
+    std::shared_ptr<ErrorSock::Pipes> mock_client_socket_pipes{
+        ConnectClient<ErrorSock>(std::as_bytes(std::span(all_requests)))
+    };
+
+    // Wait up to one minute for the last reply from the server
+    std::string actual;
+    char buf[0x10000] = {};
+    int attempts = 1000;
+    while (attempts > 0)
+    {
+        ssize_t bytes_read = mock_client_socket_pipes->send.GetBytes(buf, sizeof(buf), 0);
+        if (bytes_read > 0) {
+            actual.append(buf, bytes_read);
+            if (actual.find(strprintf("height: %d", num_requests - 1)) != std::string::npos) {
+                break;
+            }
+        }
+        std::this_thread::sleep_for(10ms);
+        --attempts;
+    }
+
+    // All replies were received
+    for (int i = 0; i < num_requests; i++) {
+        BOOST_REQUIRE(actual.find(strprintf("height: %d", i)) != std::string::npos);
+    }
+
+    // Close the keep-alive connection
+    server.DisconnectAllClients();
+
+    server.InterruptNet();
+    server.JoinSocketsThreads();
+    server.StopListening();
+}
+
 BOOST_AUTO_TEST_SUITE_END()
diff --git a/src/test/util/setup_common.cpp b/src/test/util/setup_common.cpp
index 830fca0e..bcf63778 100644
--- a/src/test/util/setup_common.cpp
+++ b/src/test/util/setup_common.cpp
@@ -657,24 +657,6 @@ SocketTestingSetup::~SocketTestingSetup()
     CreateSock = m_create_sock_orig;
 }
 
-std::shared_ptr<DynSock::Pipes> SocketTestingSetup::ConnectClient(std::span<const std::byte> data)
-{
-    // I/O pipes for a mock Connected Socket we can read and write to.
-    auto connected_socket_pipes(std::make_shared<DynSock::Pipes>());
-
-    // Insert the payload
-    connected_socket_pipes->recv.PushBytes(data.data(), data.size());
-
-    // Create the Mock Connected Socket that represents a client.
-    // It needs I/O pipes but its queue can remain empty
-    std::unique_ptr<DynSock> connected_socket{std::make_unique<DynSock>(connected_socket_pipes)};
-
-    // Push into the queue of Accepted Sockets returned by the local CreateSock()
-    m_accepted_sockets.Push(std::move(connected_socket));
-
-    return connected_socket_pipes;
-}
-
 /**
  * @returns a real block (0000000000013b8ab2cd513b0261a14096412195a72a0c4827d229dcc7e0f7af)
  *      with 9 txs.
diff --git a/src/test/util/setup_common.h b/src/test/util/setup_common.h
index e44c7e72..7818224e 100644
--- a/src/test/util/setup_common.h
+++ b/src/test/util/setup_common.h
@@ -257,10 +257,18 @@ public:
     ~SocketTestingSetup();
 
     /**
-     * Connect to the socket with a mock client (a DynSock) and send pre-loaded data.
+     * Connect to the socket with a mock client and send pre-loaded data.
      * Returns the I/O pipes from the mock client so we can read response data sent to it.
+     * Template parameter selects the socket type: DynSock by default.
      */
-    std::shared_ptr<DynSock::Pipes> ConnectClient(std::span<const std::byte> data);
+    template <typename T = DynSock>
+    std::shared_ptr<typename T::Pipes> ConnectClient(std::span<const std::byte> data)
+    {
+        auto connected_socket_pipes(std::make_shared<typename T::Pipes>());
+        connected_socket_pipes->recv.PushBytes(data.data(), data.size());
+        m_accepted_sockets.Push(std::make_unique<T>(connected_socket_pipes));
+        return connected_socket_pipes;
+    }
 
 private:
     //! Save the original value of CreateSock here and restore it when the test ends.