diff --git a/Userland/Libraries/LibCore/Socket.cpp b/Userland/Libraries/LibCore/Socket.cpp
index dc28ed58a59..418f3a8c7a0 100644
--- a/Userland/Libraries/LibCore/Socket.cpp
+++ b/Userland/Libraries/LibCore/Socket.cpp
@@ -118,16 +118,33 @@ bool Socket::connect(const SocketAddress& address)
 bool Socket::common_connect(const struct sockaddr* addr, socklen_t addrlen)
 {
     auto connected = [this] {
-        dbgln_if(CSOCKET_DEBUG, "{} connected!", *this);
-        if (!m_connected) {
+        int so_error;
+        socklen_t so_error_len = sizeof(so_error);
+
+        int rc = getsockopt(fd(), SOL_SOCKET, SO_ERROR, &so_error, &so_error_len);
+        if (rc < 0) {
+            dbgln_if(CSOCKET_DEBUG, "Failed to check the status of SO_ERROR");
+            m_connected = false;
+            if (on_error)
+                on_error();
+        }
+
+        if (so_error == 0) {
+            dbgln_if(CSOCKET_DEBUG, "{} connected!", *this);
             m_connected = true;
             ensure_read_notifier();
-            if (m_notifier) {
-                m_notifier->remove_from_parent();
-                m_notifier = nullptr;
-            }
             if (on_connected)
                 on_connected();
+        } else {
+            dbgln_if(CSOCKET_DEBUG, "Failed to connect to {}", *this);
+            m_connected = false;
+            if (on_error)
+                on_error();
+        }
+
+        if (m_notifier) {
+            m_notifier->remove_from_parent();
+            m_notifier = nullptr;
         }
     };
     int rc = ::connect(fd(), addr, addrlen);
diff --git a/Userland/Libraries/LibCore/Socket.h b/Userland/Libraries/LibCore/Socket.h
index 58823b7fbdb..359e8a56c8e 100644
--- a/Userland/Libraries/LibCore/Socket.h
+++ b/Userland/Libraries/LibCore/Socket.h
@@ -43,6 +43,7 @@ public:
     int destination_port() const { return m_destination_port; }
 
     Function<void()> on_connected;
+    Function<void()> on_error;
     Function<void()> on_ready_to_read;
 
 protected:
diff --git a/Userland/Libraries/LibHTTP/HttpJob.cpp b/Userland/Libraries/LibHTTP/HttpJob.cpp
index d8c480c09a4..6e8d36de783 100644
--- a/Userland/Libraries/LibHTTP/HttpJob.cpp
+++ b/Userland/Libraries/LibHTTP/HttpJob.cpp
@@ -20,6 +20,12 @@ void HttpJob::start()
         dbgln_if(CHTTPJOB_DEBUG, "HttpJob: on_connected callback");
         on_socket_connected();
     };
+    m_socket->on_error = [this] {
+        dbgln_if(CHTTPJOB_DEBUG, "HttpJob: on_error callback");
+        deferred_invoke([this](auto&) {
+            did_fail(Core::NetworkJob::Error::ConnectionFailed);
+        });
+    };
     bool success = m_socket->connect(m_request.url().host(), m_request.url().port());
     if (!success) {
         deferred_invoke([this](auto&) {