diff --git a/Userland/Services/RequestServer/ConnectionCache.cpp b/Userland/Services/RequestServer/ConnectionCache.cpp
index efcb88900e..74a9b6a532 100644
--- a/Userland/Services/RequestServer/ConnectionCache.cpp
+++ b/Userland/Services/RequestServer/ConnectionCache.cpp
@@ -38,9 +38,15 @@ void request_did_finish(URL const& url, Core::Socket const* socket)
 
         auto& connection = *connection_it;
         if (connection->request_queue.is_empty()) {
+            // Immediately mark the connection as finished, as new jobs will never be run if they are queued
+            // before the deferred_invoke() below runs otherwise.
+            connection->has_started = false;
+            connection->socket->set_notifications_enabled(false);
+
             Core::deferred_invoke([&connection, &cache_entry = *it->value, key = it->key, &cache] {
-                connection->socket->set_notifications_enabled(false);
-                connection->has_started = false;
+                if (connection->has_started)
+                    return;
+
                 connection->current_url = {};
                 connection->job_data = {};
                 connection->removal_timer->on_timeout = [ptr = connection.ptr(), &cache_entry, key = move(key), &cache]() mutable {
diff --git a/Userland/Services/RequestServer/ConnectionCache.h b/Userland/Services/RequestServer/ConnectionCache.h
index 2cbd354606..564b287731 100644
--- a/Userland/Services/RequestServer/ConnectionCache.h
+++ b/Userland/Services/RequestServer/ConnectionCache.h
@@ -241,13 +241,15 @@ decltype(auto) get_or_create_connection(auto& cache, URL const& url, auto& job,
             return ReturnType { nullptr };
         }
         dbgln_if(REQUESTSERVER_DEBUG, "Immediately start request for url {} in {} - {}", url, &connection, connection.socket);
-        connection.has_started = true;
-        connection.removal_timer->stop();
-        connection.timer.start();
-        connection.current_url = url;
-        connection.job_data = decltype(connection.job_data)::create(job);
-        connection.socket->set_notifications_enabled(true);
-        connection.job_data.start(*connection.socket);
+        Core::deferred_invoke([&connection, url, &job] {
+            connection.has_started = true;
+            connection.removal_timer->stop();
+            connection.timer.start();
+            connection.current_url = url;
+            connection.job_data = decltype(connection.job_data)::create(job);
+            connection.socket->set_notifications_enabled(true);
+            connection.job_data.start(*connection.socket);
+        });
     } else {
         dbgln_if(REQUESTSERVER_DEBUG, "Enqueue request for URL {} in {} - {}", url, &connection, connection.socket);
         connection.request_queue.append(decltype(connection.job_data)::create(job));