diff --git a/src/Dotty.CLI/Commands/ConvertCommands.cs b/src/Dotty.CLI/Commands/ConvertCommands.cs
index c477b51..3545ca5 100644
--- a/src/Dotty.CLI/Commands/ConvertCommands.cs
+++ b/src/Dotty.CLI/Commands/ConvertCommands.cs
@@ -10,10 +10,14 @@ public void Register(ICoconaAppBuilder app)
     {
         app.AddSubCommand("convert", group =>
         {
-            group.AddCommand("units", ConvertUnits);
-            group.AddCommand("tobase64", ([Argument] string input) => Panel(Convert.ToBase64String(Encoding.UTF8.GetBytes(input))));
-            group.AddCommand("frombase64", ([Argument] string input) => Panel(Encoding.UTF8.GetString(Convert.FromBase64String(input))));
-        });
+            group.AddCommand("units", ConvertUnits)
+                .WithDescription("Converts a value from one unit of measurement to another");
+            group.AddCommand("tobase64", ([Argument] string input) => Panel(Convert.ToBase64String(Encoding.UTF8.GetBytes(input))))
+                .WithDescription("Converts a string to a base64 encoded string");
+            group.AddCommand("frombase64", ([Argument] string input) => Panel(Encoding.UTF8.GetString(Convert.FromBase64String(input))))
+                .WithDescription("Converts a base64 encoded string to a regular string");
+        })
+        .WithDescription("Contains commands to convert values");
     }
 
 
diff --git a/src/Dotty.CLI/Commands/GenerateCommands.cs b/src/Dotty.CLI/Commands/GenerateCommands.cs
index 8d568cd..5f8d65d 100644
--- a/src/Dotty.CLI/Commands/GenerateCommands.cs
+++ b/src/Dotty.CLI/Commands/GenerateCommands.cs
@@ -7,23 +7,27 @@ public class GenerateCommands : ICommandDefinition
     public void Register(ICoconaAppBuilder app)
     {
         app.AddSubCommand("generate", group =>
-        {
-            group.AddSubCommand("random", subgroup =>
             {
-                subgroup.AddCommand("guid", () => Panel(Guid.NewGuid().ToString()));
-                
-                subgroup.AddCommand("number", ([Option('m')] int min = 0, [Option('M')] int max = 100)
-                    => Panel(Random.Shared.Next(min, max).ToString()));
+                group.AddSubCommand("random", subgroup =>
+                {
+                    subgroup.AddCommand("guid", () => Panel(Guid.NewGuid().ToString()))
+                        .WithDescription("Generates a random GUID");
 
-                subgroup
-                    .AddCommand("fromtemplate", ([Argument] string template) => Panel(new Faker().Parse(template)))
-                    .WithDescription("""
-                                     Can generate random data from a template using the Bogus library. 
-                                     For example, `generate random fromtemplate '{{name.firstName(Male)}} {{name.lastName}}'`
-                                     """);
-            });
+                    subgroup.AddCommand("number", ([Option('m')] int min = 0, [Option('M')] int max = 100)
+                            => Panel(Random.Shared.Next(min, max).ToString()))
+                        .WithDescription("Generates a random number within a range");
 
-            group.AddCommand("timestamp", (string format = "o") => Panel(DateTimeOffset.UtcNow.ToString(format)));
-        });
+                    subgroup
+                        .AddCommand("fromtemplate", ([Argument] string template) => Panel(new Faker().Parse(template)))
+                        .WithDescription("""
+                                         Can generate random data from a template using the Bogus library. 
+                                         For example, `generate random fromtemplate '{{name.firstName(Male)}} {{name.lastName}}'`
+                                         """);
+                });
+
+                group.AddCommand("timestamp", (string format = "o") => Panel(DateTimeOffset.UtcNow.ToString(format)))
+                    .WithDescription("Generates a timestamp for the current datetime with an optional format string");
+            })
+            .WithDescription("Contains commands to generate certain data");
     }
 }
\ No newline at end of file
diff --git a/src/Dotty.CLI/Commands/IntroduceCommand.cs b/src/Dotty.CLI/Commands/IntroduceCommand.cs
index ea0c05e..674de9b 100644
--- a/src/Dotty.CLI/Commands/IntroduceCommand.cs
+++ b/src/Dotty.CLI/Commands/IntroduceCommand.cs
@@ -6,18 +6,24 @@ public void Register(ICoconaAppBuilder app)
     {
         app.AddSubCommand("introduce", group =>
         {
-            group.AddCommand("talk", () => Panel("Welcome to this talk on crafting modern CLI tools using .NET"));
-            group.AddCommand("speaker", IntroduceSpeaker);
+            group.AddCommand("talk", () => Panel("Welcome to this talk on crafting modern CLI tools using .NET"))
+                .WithDescription("Introduces the talk");
+
+            group.AddCommand("speaker", IntroduceSpeaker)
+                .WithDescription("Introduces the speaker");
+
             group.AddCommand("yourself", () =>
-            {
-                Panel("""
-                      Hi, I'm Dotty, a CLI tool written in C# with dotnet. 
-                      I'm an assistant here to help you with various tasks!
-
-                      PS: My name is a play on words: Dotnet + Clippy. Remember Clippy? 
-                      """);
-            });
-        });
+                {
+                    Panel("""
+                          Hi, I'm Dotty, a CLI tool written in C# with dotnet. 
+                          I'm an assistant here to help you with various tasks!
+
+                          PS: My name is a play on words: Dotnet + Clippy. Remember Clippy? 
+                          """);
+                })
+                .WithDescription("Introduces Dotty");
+        })
+        .WithDescription("Contains commands to introduce various elements");
     }
 
     private static void IntroduceSpeaker([Option('n')] string? name = null)
diff --git a/src/Dotty.CLI/Commands/PresentCommands.cs b/src/Dotty.CLI/Commands/PresentCommands.cs
index 4f43a9d..4e7f5b0 100644
--- a/src/Dotty.CLI/Commands/PresentCommands.cs
+++ b/src/Dotty.CLI/Commands/PresentCommands.cs
@@ -16,6 +16,7 @@ public void Register(ICoconaAppBuilder app)
                     UseShellExecute = true
                 });
             });
-        });
+        })
+        .WithDescription("Opens the presentation slides for the talk");
     }
 }
\ No newline at end of file
diff --git a/src/Dotty.CLI/Commands/SimpleCommands.cs b/src/Dotty.CLI/Commands/SimpleCommands.cs
index dd47cff..0758da4 100644
--- a/src/Dotty.CLI/Commands/SimpleCommands.cs
+++ b/src/Dotty.CLI/Commands/SimpleCommands.cs
@@ -8,7 +8,8 @@ public class SimpleCommands : ICommandDefinition
 {
     public void Register(ICoconaAppBuilder app)
     {
-        app.AddCommand("greet", ([Argument] string subject) => Panel($"Hello, {subject}!"));
+        app.AddCommand("greet", ([Argument] string subject) => Panel($"Hello, {subject}!"))
+            .WithDescription("Greets any subject");
 
         app.AddCommand(([FromService] ICoconaApplicationMetadataProvider metadataProvider, [FromService] ICoconaHelpMessageBuilder helpProvider) =>
         {
diff --git a/src/Dotty.CLI/Commands/WeatherCommands.cs b/src/Dotty.CLI/Commands/WeatherCommands.cs
index ebfb162..8b27d9b 100644
--- a/src/Dotty.CLI/Commands/WeatherCommands.cs
+++ b/src/Dotty.CLI/Commands/WeatherCommands.cs
@@ -9,7 +9,8 @@ public class WeatherCommands : ICommandDefinition
 {
     public void Register(ICoconaAppBuilder app)
     {
-        app.AddCommand("weather", ExecuteWeatherCommand);
+        app.AddCommand("weather", ExecuteWeatherCommand)
+            .WithDescription("Gets the weather for a specific city");
     }
 
     private static async Task ExecuteWeatherCommand([FromService] IWeatherService weatherService, [Argument] string city)