diff --git a/book/chapters/config.md b/book/chapters/config.md
index 8a726102e..8991bf9ee 100644
--- a/book/chapters/config.md
+++ b/book/chapters/config.md
@@ -323,6 +323,10 @@ char literalQuote = '\'';
 uint8_t maximumLayers{255};
 /// the separator used to separator parent layers
 char parentSeparatorChar{'.'};
+/// comment default values
+bool commentDefaultsBool = false;
+/// specify the config reader should collapse repeated field names to a single vector
+bool allowMultipleDuplicateFields{false};
 /// Specify the configuration index to use for arrayed sections
 uint16_t configIndex{0};
 /// Specify the configuration section that should be used
@@ -341,6 +345,10 @@ These can be modified via setter functions
   and value
 - `ConfigBase *quoteCharacter(char qString, char literalChar)` :specify the
   characters to use around strings and single characters
+- `ConfigBase *commentDefaults(bool comDef)` : set to true to comment lines with
+  a default value
+- `ConfigBase *allowDuplicateFields(bool value)` :set to true to allow duplicate
+  fields to be merged even if not sequential
 - `ConfigBase *maxLayers(uint8_t layers)` : specify the maximum number of parent
   layers to process. This is useful to limit processing for larger config files
 - `ConfigBase *parentSeparator(char sep)` : specify the character to separate
@@ -450,8 +458,8 @@ positional, or the environment variable name. When generating a config file it
 will create an option name in following priority.
 
 1. First long name
-2. Positional name
-3. First short name
+2. First short name
+3. Positional name
 4. Environment name
 
 In config files the name will be enclosed in quotes if there is any potential
diff --git a/examples/CMakeLists.txt b/examples/CMakeLists.txt
index 24a5be64a..1173d6b6e 100644
--- a/examples/CMakeLists.txt
+++ b/examples/CMakeLists.txt
@@ -251,6 +251,11 @@ add_cli_exe(custom_parse custom_parse.cpp)
 add_test(NAME cp_test COMMAND custom_parse --dv 1.7)
 set_property(TEST cp_test PROPERTY PASS_REGULAR_EXPRESSION "called correct")
 
+#-----------------------------------------------------
+add_cli_exe(help_usage help_usage.cpp)
+add_test(NAME help_use COMMAND help_usage --help)
+set_property(TEST help_use PROPERTY PASS_REGULAR_EXPRESSION "[1..9]")
+
 #------------------------------------------------
 # This executable is for manual testing and is expected to change regularly
 
diff --git a/examples/help_usage.cpp b/examples/help_usage.cpp
index 6b7d19011..d747cb3cf 100644
--- a/examples/help_usage.cpp
+++ b/examples/help_usage.cpp
@@ -1,4 +1,4 @@
-// Copyright (c) 2017-2023, University of Cincinnati, developed by Henry Schreiner
+// Copyright (c) 2017-2024, University of Cincinnati, developed by Henry Schreiner
 // under NSF AWARD 1414736 and by the respective contributors.
 // All rights reserved.
 //
@@ -9,7 +9,7 @@
 
 int main(int argc, char **argv) {
     std::string input_file_name, output_file_name;
-    int level, subopt;
+    int level{5}, subopt{0};
 
     // app caption
     CLI::App app{"CLI11 help"};
@@ -47,26 +47,29 @@ int main(int argc, char **argv) {
 
 /*
 $ ./help_usage -h
-CLI11 help
-Usage: help_usage <command> [options] <input-file> <output-file>
+  CLI11 help
 
-Options:
-  -h,--help
+OPTIONS:
+  -h,     --help
 
-Subcommands:
+SUBCOMMANDS:
 e
   encode
-  Positionals:
-    input                       input file
-    output                      output file
-  Options:
-    -l,--level [1..9]           encoding level
-    -K,--remove INT             remove input file
-    -s,--suboption              suboption
+
+POSITIONALS:
+  input                       input file
+  output                      output file
+
+OPTIONS:
+  -l,     --level [1..9]      encoding level
+  -R,     --remove            remove input file
+  -s,     --suboption         suboption
+
 
 d
   decode
-  Positionals:
-    input                       input file
-    output                      output file
+
+POSITIONALS:
+  input                       input file
+  output                      output file
 */
diff --git a/include/CLI/ConfigFwd.hpp b/include/CLI/ConfigFwd.hpp
index 3f8ffdb7f..ef1c83d9e 100644
--- a/include/CLI/ConfigFwd.hpp
+++ b/include/CLI/ConfigFwd.hpp
@@ -102,10 +102,12 @@ class ConfigBase : public Config {
     uint8_t maximumLayers{255};
     /// the separator used to separator parent layers
     char parentSeparatorChar{'.'};
-    /// Specify the configuration index to use for arrayed sections
-    int16_t configIndex{-1};
+    /// comment default values
+    bool commentDefaultsBool = false;
     /// specify the config reader should collapse repeated field names to a single vector
     bool allowMultipleDuplicateFields{false};
+    /// Specify the configuration index to use for arrayed sections
+    int16_t configIndex{-1};
     /// Specify the configuration section that should be used
     std::string configSection{};
 
@@ -151,6 +153,11 @@ class ConfigBase : public Config {
         parentSeparatorChar = sep;
         return this;
     }
+    /// comment default value options
+    ConfigBase *commentDefaults(bool comDef = true) {
+        commentDefaultsBool = comDef;
+        return this;
+    }
     /// get a reference to the configuration section
     std::string &sectionRef() { return configSection; }
     /// get the section
diff --git a/include/CLI/Option.hpp b/include/CLI/Option.hpp
index f6f848aa7..24acc82d3 100644
--- a/include/CLI/Option.hpp
+++ b/include/CLI/Option.hpp
@@ -547,7 +547,7 @@ class Option : public OptionBase<Option> {
 
     /// Get the flag names with specified default values
     CLI11_NODISCARD const std::vector<std::string> &get_fnames() const { return fnames_; }
-    /// Get a single name for the option, first of lname, pname, sname, envname
+    /// Get a single name for the option, first of lname, sname, pname, envname
     CLI11_NODISCARD const std::string &get_single_name() const {
         if(!lnames_.empty()) {
             return lnames_[0];
diff --git a/include/CLI/impl/Config_inl.hpp b/include/CLI/impl/Config_inl.hpp
index 83cd44326..4979d8746 100644
--- a/include/CLI/impl/Config_inl.hpp
+++ b/include/CLI/impl/Config_inl.hpp
@@ -518,9 +518,7 @@ ConfigBase::to_config(const App *app, bool default_also, bool write_description,
     std::vector<std::string> groups = app->get_groups();
     bool defaultUsed = false;
     groups.insert(groups.begin(), std::string("OPTIONS"));
-    if(write_description && (app->get_configurable() || app->get_parent() == nullptr || app->get_name().empty())) {
-        out << commentLead << detail::fix_newlines(commentLead, app->get_description()) << '\n';
-    }
+
     for(auto &group : groups) {
         if(group == "OPTIONS" || group.empty()) {
             if(defaultUsed) {
@@ -529,10 +527,9 @@ ConfigBase::to_config(const App *app, bool default_also, bool write_description,
             defaultUsed = true;
         }
         if(write_description && group != "OPTIONS" && !group.empty()) {
-            out << '\n' << commentLead << group << " Options\n";
+            out << '\n' << commentChar << commentLead << group << " Options\n";
         }
         for(const Option *opt : app->get_options({})) {
-
             // Only process options that are configurable
             if(opt->get_configurable()) {
                 if(opt->get_group() != group) {
@@ -548,14 +545,18 @@ ConfigBase::to_config(const App *app, bool default_also, bool write_description,
                 std::string value = detail::ini_join(
                     opt->reduced_results(), arraySeparator, arrayStart, arrayEnd, stringQuote, literalQuote);
 
+                bool isDefault = false;
                 if(value.empty() && default_also) {
                     if(!opt->get_default_str().empty()) {
                         value = detail::convert_arg_for_ini(opt->get_default_str(), stringQuote, literalQuote, false);
                     } else if(opt->get_expected_min() == 0) {
                         value = "false";
-                    } else if(opt->get_run_callback_for_default()) {
+                    } else if(opt->get_run_callback_for_default() || !opt->get_required()) {
                         value = "\"\"";  // empty string default value
+                    } else {
+                        value = "\"<REQUIRED>\"";
                     }
+                    isDefault = true;
                 }
 
                 if(!value.empty()) {
@@ -581,18 +582,23 @@ ConfigBase::to_config(const App *app, bool default_also, bool write_description,
                         }
                     }
                     if(write_description && opt->has_description()) {
-                        out << '\n';
+                        if(out.tellp() != std::streampos(0)) {
+                            out << '\n';
+                        }
                         out << commentLead << detail::fix_newlines(commentLead, opt->get_description()) << '\n';
                     }
                     clean_name_string(single_name, keyChars);
 
                     std::string name = prefix + single_name;
-
+                    if(commentDefaultsBool && isDefault) {
+                        name = commentChar + name;
+                    }
                     out << name << valueDelimiter << value << '\n';
                 }
             }
         }
     }
+
     auto subcommands = app->get_subcommands({});
     for(const App *subcom : subcommands) {
         if(subcom->get_name().empty()) {
@@ -650,6 +656,11 @@ ConfigBase::to_config(const App *app, bool default_also, bool write_description,
         }
     }
 
+    if(write_description && !out.str().empty()) {
+        std::string outString =
+            commentChar + commentLead + detail::fix_newlines(commentChar + commentLead, app->get_description()) + '\n';
+        return outString + out.str();
+    }
     return out.str();
 }
 // [CLI11:config_inl_hpp:end]
diff --git a/tests/ConfigFileTest.cpp b/tests/ConfigFileTest.cpp
index 00e8fa0f7..86d9c42eb 100644
--- a/tests/ConfigFileTest.cpp
+++ b/tests/ConfigFileTest.cpp
@@ -3189,6 +3189,9 @@ TEST_CASE_METHOD(TApp, "TomlOutputHiddenOptions", "[config]") {
 TEST_CASE_METHOD(TApp, "TomlOutputAppMultiLineDescription", "[config]") {
     app.description("Some short app description.\n"
                     "That has multiple lines.");
+    // for descriptions to show up needs an option that was set
+    app.add_option("--test");
+    args = {"--test", "55"};
     run();
 
     std::string str = app.config_to_str(true, true);
@@ -3376,6 +3379,24 @@ TEST_CASE_METHOD(TApp, "TomlOutputDefault", "[config]") {
 
     str = app.config_to_str(true);
     CHECK_THAT(str, Contains("simple=7"));
+
+    app.get_config_formatter_base()->commentDefaults();
+    str = app.config_to_str(true);
+    CHECK_THAT(str, Contains("#simple=7"));
+}
+
+TEST_CASE_METHOD(TApp, "TomlOutputDefaultRequired", "[config]") {
+
+    int v{7};
+    auto *opt = app.add_option("--simple", v);
+    opt->required()->run_callback_for_default(false);
+
+    std::string str = app.config_to_str(true);
+    CHECK_THAT(str, Contains("simple=\"<REQUIRED>\""));
+
+    opt->required(false);
+    str = app.config_to_str(true);
+    CHECK_THAT(str, Contains("simple=\"\""));
 }
 
 TEST_CASE_METHOD(TApp, "TomlOutputSubcom", "[config]") {
@@ -3690,6 +3711,10 @@ TEST_CASE_METHOD(TApp, "IniOutputAppMultiLineDescription", "[config]") {
     app.description("Some short app description.\n"
                     "That has multiple lines.");
     app.config_formatter(std::make_shared<CLI::ConfigINI>());
+
+    // for descriptions to show up needs an option that was set
+    app.add_option("--test");
+    args = {"--test", "66"};
     run();
 
     std::string str = app.config_to_str(true, true);