diff --git a/Ladybird/CMakeLists.txt b/Ladybird/CMakeLists.txt
index 308cd9423e18f..dc31588753321 100644
--- a/Ladybird/CMakeLists.txt
+++ b/Ladybird/CMakeLists.txt
@@ -114,7 +114,8 @@ endfunction()
 
 add_executable(headless-browser
     ${LADYBIRD_SOURCE_DIR}/Userland/Utilities/headless-browser.cpp
-    ${LADYBIRD_SOURCES})
+    ${LADYBIRD_SOURCES}
+        ../Userland/Libraries/LibRequests/NetworkErrorEnum.h)
 
 target_include_directories(headless-browser PRIVATE ${CMAKE_CURRENT_BINARY_DIR})
 target_include_directories(headless-browser PRIVATE ${LADYBIRD_SOURCE_DIR}/Userland/)
diff --git a/Userland/Libraries/LibRequests/CMakeLists.txt b/Userland/Libraries/LibRequests/CMakeLists.txt
index 2923a5e2851b4..3228d65e5ef71 100644
--- a/Userland/Libraries/LibRequests/CMakeLists.txt
+++ b/Userland/Libraries/LibRequests/CMakeLists.txt
@@ -2,6 +2,7 @@ set(SOURCES
     Request.cpp
     RequestClient.cpp
     WebSocket.cpp
+    NetworkErrorEnum.h
 )
 
 set(GENERATED_SOURCES
diff --git a/Userland/Libraries/LibRequests/NetworkErrorEnum.h b/Userland/Libraries/LibRequests/NetworkErrorEnum.h
new file mode 100644
index 0000000000000..95eb458234f94
--- /dev/null
+++ b/Userland/Libraries/LibRequests/NetworkErrorEnum.h
@@ -0,0 +1,22 @@
+/*
+ * Copyright (c) 2024, the Ladybird developers.
+ *
+ * SPDX-License-Identifier: BSD-2-Clause
+ */
+
+#pragma once
+
+namespace Requests {
+
+enum class NetworkError {
+    UnableToResolveProxy,
+    UnableToResolveHost,
+    UnableToConnect,
+    TimeoutReached,
+    TooManyRedirects,
+    SSLHandshakeFailed,
+    SSLVerificationFailed,
+    Unknown
+};
+
+}
diff --git a/Userland/Libraries/LibRequests/Request.cpp b/Userland/Libraries/LibRequests/Request.cpp
index 34272fc57f817..b02f5ba19be60 100644
--- a/Userland/Libraries/LibRequests/Request.cpp
+++ b/Userland/Libraries/LibRequests/Request.cpp
@@ -52,13 +52,14 @@ void Request::set_buffered_request_finished_callback(BufferedRequestFinished on_
         m_internal_buffered_data->response_code = move(response_code);
     };
 
-    on_finish = [this, on_buffered_request_finished = move(on_buffered_request_finished)](auto success, auto total_size) {
+    on_finish = [this, on_buffered_request_finished = move(on_buffered_request_finished)](auto success, auto total_size, auto network_error) {
         auto output_buffer = ByteBuffer::create_uninitialized(m_internal_buffered_data->payload_stream.used_buffer_size()).release_value_but_fixme_should_propagate_errors();
         m_internal_buffered_data->payload_stream.read_until_filled(output_buffer).release_value_but_fixme_should_propagate_errors();
 
         on_buffered_request_finished(
             success,
             total_size,
+            network_error,
             m_internal_buffered_data->response_headers,
             m_internal_buffered_data->response_code,
             output_buffer);
@@ -81,10 +82,10 @@ void Request::set_unbuffered_request_callbacks(HeadersReceived on_headers_receiv
     set_up_internal_stream_data(move(on_data_received));
 }
 
-void Request::did_finish(Badge<RequestClient>, bool success, u64 total_size)
+void Request::did_finish(Badge<RequestClient>, bool success, u64 total_size, Optional<NetworkError> const& network_error)
 {
     if (on_finish)
-        on_finish(success, total_size);
+        on_finish(success, total_size, network_error);
 }
 
 void Request::did_receive_headers(Badge<RequestClient>, HTTP::HeaderMap const& response_headers, Optional<u32> response_code)
@@ -113,9 +114,10 @@ void Request::set_up_internal_stream_data(DataReceived on_data_available)
         m_internal_stream_data->read_stream = MUST(Core::File::adopt_fd(fd(), Core::File::OpenMode::Read));
 
     auto user_on_finish = move(on_finish);
-    on_finish = [this](auto success, auto total_size) {
+    on_finish = [this](auto success, auto total_size, auto network_error) {
         m_internal_stream_data->success = success;
         m_internal_stream_data->total_size = total_size;
+        m_internal_stream_data->network_error = network_error;
         m_internal_stream_data->request_done = true;
         m_internal_stream_data->on_finish();
     };
@@ -123,7 +125,7 @@ void Request::set_up_internal_stream_data(DataReceived on_data_available)
     m_internal_stream_data->on_finish = [this, user_on_finish = move(user_on_finish)]() {
         if (!m_internal_stream_data->user_finish_called && m_internal_stream_data->read_stream->is_eof()) {
             m_internal_stream_data->user_finish_called = true;
-            user_on_finish(m_internal_stream_data->success, m_internal_stream_data->total_size);
+            user_on_finish(m_internal_stream_data->success, m_internal_stream_data->total_size, m_internal_stream_data->network_error);
         }
     };
 
diff --git a/Userland/Libraries/LibRequests/Request.h b/Userland/Libraries/LibRequests/Request.h
index de15368d5ac93..57ab51a67a40f 100644
--- a/Userland/Libraries/LibRequests/Request.h
+++ b/Userland/Libraries/LibRequests/Request.h
@@ -6,6 +6,8 @@
 
 #pragma once
 
+#include "NetworkErrorEnum.h"
+
 #include <AK/Badge.h>
 #include <AK/ByteBuffer.h>
 #include <AK/ByteString.h>
@@ -37,7 +39,7 @@ class Request : public RefCounted<Request> {
     int fd() const { return m_fd; }
     bool stop();
 
-    using BufferedRequestFinished = Function<void(bool success, u64 total_size, HTTP::HeaderMap const& response_headers, Optional<u32> response_code, ReadonlyBytes payload)>;
+    using BufferedRequestFinished = Function<void(bool success, u64 total_size, Optional<NetworkError> const& network_error, HTTP::HeaderMap const& response_headers, Optional<u32> response_code, ReadonlyBytes payload)>;
 
     // Configure the request such that the entirety of the response data is buffered. The callback receives that data and
     // the response headers all at once. Using this method is mutually exclusive with `set_unbuffered_data_received_callback`.
@@ -45,7 +47,7 @@ class Request : public RefCounted<Request> {
 
     using HeadersReceived = Function<void(HTTP::HeaderMap const& response_headers, Optional<u32> response_code)>;
     using DataReceived = Function<void(ReadonlyBytes data)>;
-    using RequestFinished = Function<void(bool success, u64 total_size)>;
+    using RequestFinished = Function<void(bool success, u64 total_size, Optional<NetworkError> network_error)>;
 
     // Configure the request such that the response data is provided unbuffered as it is received. Using this method is
     // mutually exclusive with `set_buffered_request_finished_callback`.
@@ -53,7 +55,7 @@ class Request : public RefCounted<Request> {
 
     Function<CertificateAndKey()> on_certificate_requested;
 
-    void did_finish(Badge<RequestClient>, bool success, u64 total_size);
+    void did_finish(Badge<RequestClient>, bool success, u64 total_size, Optional<NetworkError> const& network_error);
     void did_receive_headers(Badge<RequestClient>, HTTP::HeaderMap const& response_headers, Optional<u32> response_code);
     void did_request_certificates(Badge<RequestClient>);
 
@@ -93,6 +95,7 @@ class Request : public RefCounted<Request> {
         RefPtr<Core::Notifier> read_notifier;
         bool success;
         u32 total_size { 0 };
+        Optional<NetworkError> network_error;
         bool request_done { false };
         Function<void()> on_finish {};
         bool user_finish_called { false };
diff --git a/Userland/Libraries/LibRequests/RequestClient.cpp b/Userland/Libraries/LibRequests/RequestClient.cpp
index f74fc07adc711..caf332401b295 100644
--- a/Userland/Libraries/LibRequests/RequestClient.cpp
+++ b/Userland/Libraries/LibRequests/RequestClient.cpp
@@ -68,11 +68,11 @@ bool RequestClient::set_certificate(Badge<Request>, Request& request, ByteString
     return IPCProxy::set_certificate(request.id(), move(certificate), move(key));
 }
 
-void RequestClient::request_finished(i32 request_id, bool success, u64 total_size)
+void RequestClient::request_finished(i32 request_id, bool success, u64 total_size, Optional<NetworkError> const& network_error)
 {
     RefPtr<Request> request;
     if ((request = m_requests.get(request_id).value_or(nullptr))) {
-        request->did_finish({}, success, total_size);
+        request->did_finish({}, success, total_size, network_error);
     }
     m_requests.remove(request_id);
 }
diff --git a/Userland/Libraries/LibRequests/RequestClient.h b/Userland/Libraries/LibRequests/RequestClient.h
index 3136811936f31..207ba09acd32b 100644
--- a/Userland/Libraries/LibRequests/RequestClient.h
+++ b/Userland/Libraries/LibRequests/RequestClient.h
@@ -40,7 +40,7 @@ class RequestClient final
     virtual void die() override;
 
     virtual void request_started(i32, IPC::File const&) override;
-    virtual void request_finished(i32, bool, u64) override;
+    virtual void request_finished(i32, bool, u64, Optional<NetworkError> const&) override;
     virtual void certificate_requested(i32) override;
     virtual void headers_became_available(i32, HTTP::HeaderMap const&, Optional<u32> const&) override;
 
diff --git a/Userland/Libraries/LibWeb/Loader/ResourceLoader.cpp b/Userland/Libraries/LibWeb/Loader/ResourceLoader.cpp
index 3694fbfd53264..d553511d1ad94 100644
--- a/Userland/Libraries/LibWeb/Loader/ResourceLoader.cpp
+++ b/Userland/Libraries/LibWeb/Loader/ResourceLoader.cpp
@@ -178,6 +178,28 @@ static void log_filtered_request(LoadRequest const& request)
     dbgln("ResourceLoader: Filtered request to: \"{}\"", url_for_logging);
 }
 
+static StringView network_error_to_string_view(Requests::NetworkError const& network_error)
+{
+    switch (network_error) {
+    case Requests::NetworkError::UnableToResolveProxy:
+        return "Unable to resolve proxy"sv;
+    case Requests::NetworkError::UnableToResolveHost:
+        return "Unable to resolve host"sv;
+    case Requests::NetworkError::UnableToConnect:
+        return "Unable to connect"sv;
+    case Requests::NetworkError::TimeoutReached:
+        return "Timeout reached"sv;
+    case Requests::NetworkError::TooManyRedirects:
+        return "Too many redirects"sv;
+    case Requests::NetworkError::SSLHandshakeFailed:
+        return "SSL handshake failed"sv;
+    case Requests::NetworkError::SSLVerificationFailed:
+        return "SSL verification failed"sv;
+    default:
+        return "An unexpected network error occurred"sv;
+    }
+}
+
 static bool should_block_request(LoadRequest const& request)
 {
     auto const& url = request.url();
@@ -397,16 +419,20 @@ void ResourceLoader::load(LoadRequest& request, SuccessCallback success_callback
             timer->start();
         }
 
-        auto on_buffered_request_finished = [this, success_callback = move(success_callback), error_callback = move(error_callback), request, &protocol_request = *protocol_request](bool success, auto, auto& response_headers, auto status_code, ReadonlyBytes payload) mutable {
+        auto on_buffered_request_finished = [this, success_callback = move(success_callback), error_callback = move(error_callback), request, &protocol_request = *protocol_request](bool success, auto, auto const& network_error, auto& response_headers, auto status_code, ReadonlyBytes payload) mutable {
             handle_network_response_headers(request, response_headers);
             finish_network_request(protocol_request);
 
             if (!success || (status_code.has_value() && *status_code >= 400 && *status_code <= 599 && (payload.is_empty() || !request.is_main_resource()))) {
                 StringBuilder error_builder;
-                if (status_code.has_value())
-                    error_builder.appendff("Load failed: {}", *status_code);
+                if (network_error.has_value())
+                    error_builder.appendff("{}", network_error_to_string_view(*network_error));
                 else
                     error_builder.append("Load failed"sv);
+
+                if (status_code.has_value())
+                    error_builder.appendff(" (status code: {})", *status_code);
+
                 log_failure(request, error_builder.string_view());
                 if (error_callback)
                     error_callback(error_builder.to_byte_string(), status_code, payload, response_headers);
@@ -460,7 +486,7 @@ void ResourceLoader::load_unbuffered(LoadRequest& request, OnHeadersReceived on_
         on_data_received(data);
     };
 
-    auto protocol_complete = [this, on_complete = move(on_complete), request, &protocol_request = *protocol_request](bool success, u64) {
+    auto protocol_complete = [this, on_complete = move(on_complete), request, &protocol_request = *protocol_request](bool success, u64, Optional<Requests::NetworkError> const&) {
         finish_network_request(protocol_request);
 
         if (success) {
diff --git a/Userland/Services/RequestServer/ConnectionFromClient.cpp b/Userland/Services/RequestServer/ConnectionFromClient.cpp
index 95b6de61e873d..fe5d45eacde24 100644
--- a/Userland/Services/RequestServer/ConnectionFromClient.cpp
+++ b/Userland/Services/RequestServer/ConnectionFromClient.cpp
@@ -12,6 +12,7 @@
 #include <LibCore/EventLoop.h>
 #include <LibCore/Proxy.h>
 #include <LibCore/Socket.h>
+#include <LibRequests/NetworkErrorEnum.h>
 #include <LibWebSocket/ConnectionInfo.h>
 #include <LibWebSocket/Message.h>
 #include <RequestServer/ConnectionFromClient.h>
@@ -243,7 +244,7 @@ void ConnectionFromClient::start_request(i32 request_id, ByteString const& metho
 {
     if (!url.is_valid()) {
         dbgln("StartRequest: Invalid URL requested: '{}'", url);
-        async_request_finished(request_id, false, 0);
+        async_request_finished(request_id, false, 0, {});
         return;
     }
 
@@ -320,6 +321,28 @@ void ConnectionFromClient::start_request(i32 request_id, ByteString const& metho
     m_active_requests.set(request_id, move(request));
 }
 
+static Requests::NetworkError map_curl_code_to_network_error(CURLcode const& code)
+{
+    switch (code) {
+    case CURLE_COULDNT_RESOLVE_HOST:
+        return Requests::NetworkError::UnableToResolveHost;
+    case CURLE_COULDNT_RESOLVE_PROXY:
+        return Requests::NetworkError::UnableToResolveProxy;
+    case CURLE_COULDNT_CONNECT:
+        return Requests::NetworkError::UnableToConnect;
+    case CURLE_OPERATION_TIMEDOUT:
+        return Requests::NetworkError::TimeoutReached;
+    case CURLE_TOO_MANY_REDIRECTS:
+        return Requests::NetworkError::TooManyRedirects;
+    case CURLE_SSL_CONNECT_ERROR:
+        return Requests::NetworkError::SSLHandshakeFailed;
+    case CURLE_PEER_FAILED_VERIFICATION:
+        return Requests::NetworkError::SSLVerificationFailed;
+    default:
+        return Requests::NetworkError::Unknown;
+    }
+}
+
 void ConnectionFromClient::check_active_requests()
 {
     int msgs_in_queue = 0;
@@ -332,7 +355,20 @@ void ConnectionFromClient::check_active_requests()
         VERIFY(result == CURLE_OK);
         request->flush_headers_if_needed();
 
-        async_request_finished(request->request_id, msg->data.result == CURLE_OK, request->downloaded_so_far);
+        auto result_code = msg->data.result;
+
+        Optional<Requests::NetworkError> network_error;
+        bool const request_was_successful = result_code == CURLE_OK;
+        if (!request_was_successful) {
+            network_error = map_curl_code_to_network_error(result_code);
+
+            if (network_error.has_value() && network_error.value() == Requests::NetworkError::Unknown) {
+                char const* curl_error_message = curl_easy_strerror(result_code);
+                dbgln("ConnectionFromClient: Unable to map error ({}), message: \"\033[31;1m{}\033[0m\"", static_cast<int>(result_code), curl_error_message);
+            }
+        }
+
+        async_request_finished(request->request_id, request_was_successful, request->downloaded_so_far, network_error);
 
         m_active_requests.remove(request->request_id);
     }
diff --git a/Userland/Services/RequestServer/RequestClient.ipc b/Userland/Services/RequestServer/RequestClient.ipc
index 772beb9912ec1..b51adadb5531b 100644
--- a/Userland/Services/RequestServer/RequestClient.ipc
+++ b/Userland/Services/RequestServer/RequestClient.ipc
@@ -1,10 +1,11 @@
 #include <LibHTTP/HeaderMap.h>
+#include <LibRequests/NetworkErrorEnum.h>
 #include <LibURL/URL.h>
 
 endpoint RequestClient
 {
     request_started(i32 request_id, IPC::File fd) =|
-    request_finished(i32 request_id, bool success, u64 total_size) =|
+    request_finished(i32 request_id, bool success, u64 total_size, Optional<Requests::NetworkError> network_error) =|
     headers_became_available(i32 request_id, HTTP::HeaderMap response_headers, Optional<u32> status_code) =|
 
     // Websocket API