diff --git a/include/CLI/App.hpp b/include/CLI/App.hpp
index 8965159d9..482b1b749 100644
--- a/include/CLI/App.hpp
+++ b/include/CLI/App.hpp
@@ -2253,10 +2253,13 @@ class App {
         }
 
         if(require_option_min_ > used_options || (require_option_max_ > 0 && require_option_max_ < used_options)) {
-            auto option_list = detail::join(options_, [](const Option_p &ptr) { return ptr->get_name(false, true); });
-            if(option_list.compare(0, 10, "-h,--help,") == 0) {
-                option_list.erase(0, 10);
-            }
+            auto option_list = detail::join(options_, [this](const Option_p &ptr) {
+                if(ptr.get() == help_ptr_ || ptr.get() == help_all_ptr_) {
+                    return std::string{};
+                }
+                return ptr->get_name(false, true);
+            });
+
             auto subc_list = get_subcommands([](App *app) { return ((app->get_name().empty()) && (!app->disabled_)); });
             if(!subc_list.empty()) {
                 option_list += "," + detail::join(subc_list, [](const App *app) { return app->get_display_name(); });
diff --git a/include/CLI/StringTools.hpp b/include/CLI/StringTools.hpp
index 1500b8219..e1f0df7e0 100644
--- a/include/CLI/StringTools.hpp
+++ b/include/CLI/StringTools.hpp
@@ -76,10 +76,14 @@ std::string join(const T &v, Callable func, std::string delim = ",") {
     std::ostringstream s;
     auto beg = std::begin(v);
     auto end = std::end(v);
-    if(beg != end)
-        s << func(*beg++);
+    auto loc = s.tellp();
     while(beg != end) {
-        s << delim << func(*beg++);
+        auto nloc = s.tellp();
+        if(nloc > loc) {
+            s << delim;
+            loc = nloc;
+        }
+        s << func(*beg++);
     }
     return s.str();
 }
diff --git a/tests/AppTest.cpp b/tests/AppTest.cpp
index b0ca787af..6742a5052 100644
--- a/tests/AppTest.cpp
+++ b/tests/AppTest.cpp
@@ -135,11 +135,14 @@ TEST_F(TApp, RequireOptionsError) {
     app.add_flag("-c");
     app.add_flag("--q");
     app.add_flag("--this,--that");
+    app.set_help_flag("-h,--help");
+    app.set_help_all_flag("--help_all");
     app.require_option(1, 2);
     try {
         app.parse("-c --q --this --that");
     } catch(const CLI::RequiredError &re) {
         EXPECT_THAT(re.what(), Not(HasSubstr("-h,--help")));
+        EXPECT_THAT(re.what(), Not(HasSubstr("help_all")));
     }
 
     EXPECT_NO_THROW(app.parse("-c --q"));