diff --git a/services/proxy/pkg/server/debug/server.go b/services/proxy/pkg/server/debug/server.go
index f73685496..216135910 100644
--- a/services/proxy/pkg/server/debug/server.go
+++ b/services/proxy/pkg/server/debug/server.go
@@ -18,7 +18,8 @@ func Server(opts ...Option) (*http.Server, error) {
 
 	checkHandler := handlers.NewCheckHandler(
 		handlers.NewCheckHandlerConfiguration().
-			WithLogger(options.Logger),
+			WithLogger(options.Logger).
+			WithCheck("web reachability", handlers.NewHTTPCheck(options.Config.HTTP.Addr)),
 	)
 
 	var configDumpFunc http.HandlerFunc = configDump(options.Config)
diff --git a/services/settings/pkg/server/debug/server.go b/services/settings/pkg/server/debug/server.go
index e6d7c3b07..99179d7d4 100644
--- a/services/settings/pkg/server/debug/server.go
+++ b/services/settings/pkg/server/debug/server.go
@@ -14,7 +14,8 @@ func Server(opts ...Option) (*http.Server, error) {
 
 	checkHandler := handlers.NewCheckHandler(
 		handlers.NewCheckHandlerConfiguration().
-			WithLogger(options.Logger),
+			WithLogger(options.Logger).
+			WithCheck("web reachability", handlers.NewHTTPCheck(options.Config.HTTP.Addr)),
 	)
 
 	return debug.NewService(