diff --git a/include/seastar/http/exception.hh b/include/seastar/http/exception.hh
index 048a9de42f..f49e69aea8 100644
--- a/include/seastar/http/exception.hh
+++ b/include/seastar/http/exception.hh
@@ -158,6 +158,17 @@ public:
     {}
 };
 
+/**
+ * Client-side exception to report that making request timed out
+ * prior to communicating to server
+ */
+class timeout_error : public base_exception {
+public:
+    timeout_error()
+        : base_exception("client timed out", http::reply::status_type::request_timeout)
+    {}
+};
+
 SEASTAR_MODULE_EXPORT_END
 }
 
diff --git a/src/http/client.cc b/src/http/client.cc
index 2376abdf74..bd0c5b5ae2 100644
--- a/src/http/client.cc
+++ b/src/http/client.cc
@@ -252,7 +252,14 @@ future<client::connection_ptr> client::get_connection(clock_type::time_point tim
     }
 
     if (_nr_connections >= _max_connections) {
-        return _wait_con.wait().then([this, timeout] {
+        return _wait_con.wait(timeout).then_wrapped([this, timeout] (auto f) {
+            try {
+                f.get();
+            } catch (const condition_variable_timed_out&) {
+                return make_exception_future<connection_ptr>(httpd::timeout_error());
+            } catch (...) {
+                return current_exception_as_future<connection_ptr>();
+            }
             return get_connection(timeout);
         });
     }
@@ -262,9 +269,17 @@ future<client::connection_ptr> client::get_connection(clock_type::time_point tim
 
 future<client::connection_ptr> client::make_connection(clock_type::time_point timeout) {
     _total_new_connections++;
-    return _new_connections->make().then([cr = internal::client_ref(this)] (connected_socket cs) mutable {
+    return _new_connections->make().then([this, timeout, cr = internal::client_ref(this)] (connected_socket cs) mutable {
         http_log.trace("created new http connection {}", cs.local_address());
         auto con = seastar::make_shared<connection>(std::move(cs), std::move(cr));
+        if (clock_type::now() > timeout) {
+            // Factory made new connection, though it's too late already. Don't throw
+            // this effort out, but don't use it to serve current request either.
+            return put_connection(std::move(con)).then_wrapped([] (auto f) {
+                f.ignore_ready_future();
+                return make_exception_future<connection_ptr>(httpd::timeout_error());
+            });
+        }
         return make_ready_future<connection_ptr>(std::move(con));
     });
 }