diff --git a/Sources/ArgumentParser/Documentation.docc/Articles/CommandsAndSubcommands.md b/Sources/ArgumentParser/Documentation.docc/Articles/CommandsAndSubcommands.md
index 5e341e92a..0c16cf403 100644
--- a/Sources/ArgumentParser/Documentation.docc/Articles/CommandsAndSubcommands.md
+++ b/Sources/ArgumentParser/Documentation.docc/Articles/CommandsAndSubcommands.md
@@ -131,7 +131,7 @@ extension Math.Statistics {
             abstract: "Print the average of the values.",
             aliases: ["avg"])
 
-        enum Kind: String, ExpressibleByArgument {
+        enum Kind: String, ExpressibleByArgument, CaseIterable {
             case mean, median, mode
         }
 
diff --git a/Sources/ArgumentParser/Usage/HelpGenerator.swift b/Sources/ArgumentParser/Usage/HelpGenerator.swift
index 719ecd250..060ca4b96 100644
--- a/Sources/ArgumentParser/Usage/HelpGenerator.swift
+++ b/Sources/ArgumentParser/Usage/HelpGenerator.swift
@@ -114,9 +114,9 @@ internal struct HelpGenerator {
     } else {
       var usage = UsageGenerator(toolName: toolName, definition: [currentArgSet])
         .synopsis
-      if !currentCommand.configuration.subcommands.isEmpty {
+			if !currentCommand.configuration.subcommands.isEmpty {
         if usage.last != " " { usage += " " }
-        usage += "<subcommand>"
+				usage += "<subcommand>"
       }
       self.usage = usage
     }
diff --git a/Sources/ArgumentParser/Usage/UsageGenerator.swift b/Sources/ArgumentParser/Usage/UsageGenerator.swift
index e34b94ee6..19076dba3 100644
--- a/Sources/ArgumentParser/Usage/UsageGenerator.swift
+++ b/Sources/ArgumentParser/Usage/UsageGenerator.swift
@@ -104,7 +104,12 @@ extension ArgumentDefinition {
 
       switch update {
       case .unary:
-        return "\(name.synopsisString) <\(valueName)>"
+        let joinedValues = help.allValueStrings.joined(separator: "|")
+        if help.allValueStrings.count > 1 && joinedValues.count <= 40 {
+          return "\(name.synopsisString) <\(joinedValues)>"
+        } else {
+          return "\(name.synopsisString) <\(valueName)>"
+        }
       case .nullary:
         return name.synopsisString
       }
diff --git a/Tests/ArgumentParserExampleTests/MathExampleTests.swift b/Tests/ArgumentParserExampleTests/MathExampleTests.swift
index ee677a6a0..c0bc147fe 100644
--- a/Tests/ArgumentParserExampleTests/MathExampleTests.swift
+++ b/Tests/ArgumentParserExampleTests/MathExampleTests.swift
@@ -73,11 +73,33 @@ final class MathExampleTests: XCTestCase {
     try AssertExecuteCommand(command: "math help add --help", expected: helpText)
   }
   
+  func testMath_StatsHelp() throws {
+    let helpText = """
+        OVERVIEW: Calculate descriptive statistics.
+        
+        USAGE: math stats <subcommand>
+        
+        OPTIONS:
+          --version               Show the version.
+          -h, --help              Show help information.
+        
+        SUBCOMMANDS:
+          average, avg            Print the average of the values.
+          stdev                   Print the standard deviation of the values.
+          quantiles               Print the quantiles of the values (TBD).
+        
+          See 'math help stats <subcommand>' for detailed help.
+        """
+    try AssertExecuteCommand(command: "math stats -h", expected: helpText)
+    try AssertExecuteCommand(command: "math stats --help", expected: helpText)
+    try AssertExecuteCommand(command: "math help stats", expected: helpText)
+  }
+  
   func testMath_StatsMeanHelp() throws {
     let helpText = """
         OVERVIEW: Print the average of the values.
 
-        USAGE: math stats average [--kind <kind>] [<values> ...]
+        USAGE: math stats average [--kind <mean|median|mode>] [<values> ...]
 
         ARGUMENTS:
           <values>                A group of floating-point values to operate on.
@@ -128,7 +150,7 @@ final class MathExampleTests: XCTestCase {
       command: "math stats average --kind mode",
       expected: """
             Error: Please provide at least one value to calculate the mode.
-            Usage: math stats average [--kind <kind>] [<values> ...]
+            Usage: math stats average [--kind <mean|median|mode>] [<values> ...]
               See 'math stats average --help' for more information.
             """,
       exitCode: .validationFailure)
diff --git a/Tests/ArgumentParserUnitTests/HelpGenerationTests+ExpandedSynopses.swift b/Tests/ArgumentParserUnitTests/HelpGenerationTests+ExpandedSynopses.swift
new file mode 100644
index 000000000..1d11ed97a
--- /dev/null
+++ b/Tests/ArgumentParserUnitTests/HelpGenerationTests+ExpandedSynopses.swift
@@ -0,0 +1,68 @@
+//===----------------------------------------------------------*- swift -*-===//
+//
+// This source file is part of the Swift Argument Parser open source project
+//
+// Copyright (c) 2024 Apple Inc. and the Swift project authors
+// Licensed under Apache License v2.0 with Runtime Library Exception
+//
+// See https://swift.org/LICENSE.txt for license information
+//
+//===----------------------------------------------------------------------===//
+
+import XCTest
+import ArgumentParserTestHelpers
+@testable import ArgumentParser
+
+extension HelpGenerationTests {
+  enum Fruit: String, ExpressibleByArgument, CaseIterable {
+    case apple, banana, coconut, dragonFruit = "dragon-fruit", elderberry, fig, grape, honeydew
+  }
+  
+  enum Action: String, ExpressibleByArgument, CaseIterable {
+    case purchase, sample, refund = "return"
+  }
+  
+  enum Count: Int, ExpressibleByArgument, CaseIterable {
+    case zero, one, two, three, four, five, six, seven, eight, nine, ten, eleven, twelve, thirteen, fourteen, fifteen, sixteen, seventeen, eighteen, nineteen, twenty
+  }
+  
+  enum Ripeness: String, ExpressibleByArgument, CaseIterable {
+    case under, perfect, over
+  }
+
+  struct FruitStore: ParsableArguments {
+    @Argument(help: "The transaction type")
+    var action: Action = .purchase
+
+    @Argument(help: "The fruit to purchase")
+    var fruit: Fruit
+      
+    @Option(help: "The number of fruit to purchase")
+    var quantity: Count = .one
+
+    @Option(help: "The desired ripeness of fruit")
+    var ripeness: Ripeness = .perfect
+  }
+  
+  func testFruitStoreHelp() {
+    AssertHelp(.default, for: FruitStore.self, equals: """
+            USAGE: fruit_store [<action>] <fruit> [--quantity <quantity>] [--ripeness <under|perfect|over>]
+
+            ARGUMENTS:
+              <action>                The transaction type (values: purchase, sample,
+                                      return; default: purchase)
+              <fruit>                 The fruit to purchase (values: apple, banana,
+                                      coconut, dragon-fruit, elderberry, fig, grape,
+                                      honeydew)
+            
+            OPTIONS:
+              --quantity <quantity>   The number of fruit to purchase (values: 0, 1, 2, 3,
+                                      4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18,
+                                      19, 20; default: 1)
+              --ripeness <ripeness>   The desired ripeness of fruit (values: under,
+                                      perfect, over; default: perfect)
+              -h, --help              Show help information.
+            
+            """)
+  }
+}
diff --git a/Tests/ArgumentParserUnitTests/HelpGenerationTests.swift b/Tests/ArgumentParserUnitTests/HelpGenerationTests.swift
index e7a4f0408..e82a40d59 100644
--- a/Tests/ArgumentParserUnitTests/HelpGenerationTests.swift
+++ b/Tests/ArgumentParserUnitTests/HelpGenerationTests.swift
@@ -197,7 +197,7 @@ extension HelpGenerationTests {
 
   func testHelpWithDefaultValues() {
     AssertHelp(.default, for: D.self, equals: """
-      USAGE: d [<occupation>] [--name <name>] [--age <age>] [--logging <logging>] [--lucky <numbers> ...] [--optional] [--required] [--degree <degree>] [--directory <directory>] [--manual <manual>] [--unspecial <unspecial>] [--special <special>]
+      USAGE: d [<occupation>] [--name <name>] [--age <age>] [--logging <logging>] [--lucky <numbers> ...] [--optional] [--required] [--degree <degree>] [--directory <directory>] [--manual <manual>] [--unspecial <0|1>] [--special <Apple|Banana>]
 
       ARGUMENTS:
         <occupation>            Your occupation. (default: --)