diff --git a/README.md b/README.md
index 41de215..a53b526 100644
--- a/README.md
+++ b/README.md
@@ -72,7 +72,7 @@ See the [Installation Guide](#installation) when you're ready to get started.
 
 There is a complete working example of a CLI app (with a mini tutorial) in the examples directory.
 
-_This example imports the library for Node. Simply swap the Node import for the appropriate browser import if you're building a web utility. Everything else is the same for both Node and browser environments._ 
+_This example imports the library for Node. Simply swap the Node import for the appropriate browser import if you're building a web utility. Everything else is the same for both Node and browser environments._
 
 ```javascript
 import { Shell, Command } from '@author.io/node-shell'
@@ -604,9 +604,49 @@ Done!
 
 ### Customized Help/Usage Messages
 
-This library uses a vanilla dependency (i.e. no-subdependencies) called [@author.io/table](https://github.com/author/table) to format the usage and help messages of the shell. The `Table` library can be used to create your own custom screens, though most users will likely want to stick with the defaults. If you want to customize messages, the following example can be used as a starting point. The configuration options for the table can be found in the README of its repository.
+**Customizing Flag Appearance:**
+
+The `Shell` and `Command` classes can both accept several boolean attributes to customize the description of each flag within a command. Each of these is `true` by default.
+
+1. `describeDefault`: Display the default flag value.
+1. `describeOptions`: List the valid options for a flag.
+1. `describeMultipleValues`: Appends `Can be used multiple times.` to the flag description
+1. `describeRequired`: Prepends `Required.` to the flag description whenever a flag is required.
+
+<details>
+<summary>Example</summary>
+<br/>
+
+```javascript
+const c = new Command({
+  name: '...',
+  flags: {
+    name: {
+      alias: 'nm',
+      required: true,
+      default: 'Rad Dev',
+      allowMultipleValues: true,
+      options: ['Mr Awesome', 'Mrs Awesome', 'Rad Dev'],
+      description: 'Specify a name.'
+    }
+  }
+})
+```
+
+The help message for this flag would look like:
 
-_Example:_
+```sh
+Flags:
+  -name       ['nm']          Required. Specify a name. Options: Mr 
+                              Awesome, Mrs Awesome, Rad Dev. Can be 
+                              used multiple times. (Default Rad Dev)
+```
+</details>
+<br/>
+
+**Customizing the Entire Message:**
+
+This library uses a vanilla dependency (i.e. no-subdependencies) called [@author.io/table](https://github.com/author/table) to format the usage and help messages of the shell. The `Table` library can be used to create your own custom screens, though most users will likely want to stick with the defaults. If you want to customize messages, the following example can be used as a starting point. The configuration options for the table can be found in the README of its repository.
 
 ```javascript
 import { Shell, Command, Table } from '@author.io/node-shell'
diff --git a/examples/cli/index.js b/examples/cli/index.js
index 468f695..ce6abf8 100755
--- a/examples/cli/index.js
+++ b/examples/cli/index.js
@@ -1,4 +1,4 @@
-#!/usr/bin/env node --experimental-modules
+#!/usr/bin/env node --experimental-modules -r source-map-support/register
 
 import fs from 'fs'
 import path from 'path'
diff --git a/examples/cli/package.json b/examples/cli/package.json
index cebea26..1d5ec67 100644
--- a/examples/cli/package.json
+++ b/examples/cli/package.json
@@ -16,5 +16,8 @@
   "engines": {
     "node": "^12.0.0"
   },
-  "dependencies": {}
+  "dependencies": {},
+  "devDependencies": {
+    "@author.io/node-shell-debug": "^1.5.0"
+  }
 }
diff --git a/package-lock.json b/package-lock.json
index 3942fd5..68442ec 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -1,6 +1,6 @@
 {
   "name": "@author.io/shell",
-  "version": "1.5.0",
+  "version": "1.5.1",
   "lockfileVersion": 1,
   "requires": true,
   "dependencies": {
@@ -13,6 +13,1484 @@
       "version": "1.0.1",
       "resolved": "https://registry.npmjs.org/@author.io/table/-/table-1.0.1.tgz",
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+    },
+    "@babel/code-frame": {
+      "version": "7.8.3",
+      "resolved": "https://registry.npmjs.org/@babel/code-frame/-/code-frame-7.8.3.tgz",
+      "integrity": "sha512-a9gxpmdXtZEInkCSHUJDLHZVBgb1QS0jhss4cPP93EW7s+uC5bikET2twEF3KV+7rDblJcmNvTR7VJejqd2C2g==",
+      "dev": true,
+      "requires": {
+        "@babel/highlight": "^7.8.3"
+      }
+    },
+    "@babel/helper-validator-identifier": {
+      "version": "7.9.5",
+      "resolved": "https://registry.npmjs.org/@babel/helper-validator-identifier/-/helper-validator-identifier-7.9.5.tgz",
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+      "dev": true
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+      "dev": true,
+      "requires": {
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+      }
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+    "yargs": {
+      "version": "15.3.1",
+      "resolved": "https://registry.npmjs.org/yargs/-/yargs-15.3.1.tgz",
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+      "dev": true,
+      "requires": {
+        "cliui": "^6.0.0",
+        "decamelize": "^1.2.0",
+        "find-up": "^4.1.0",
+        "get-caller-file": "^2.0.1",
+        "require-directory": "^2.1.1",
+        "require-main-filename": "^2.0.0",
+        "set-blocking": "^2.0.0",
+        "string-width": "^4.2.0",
+        "which-module": "^2.0.0",
+        "y18n": "^4.0.0",
+        "yargs-parser": "^18.1.1"
+      }
+    },
+    "yargs-parser": {
+      "version": "18.1.3",
+      "resolved": "https://registry.npmjs.org/yargs-parser/-/yargs-parser-18.1.3.tgz",
+      "integrity": "sha512-o50j0JeToy/4K6OZcaQmW6lyXXKhq7csREXcDwk2omFPJEwUNOVtJKvmDr9EI1fAJZUyZcRF7kxGBWmRXudrCQ==",
+      "dev": true,
+      "requires": {
+        "camelcase": "^5.0.0",
+        "decamelize": "^1.2.0"
+      }
+    },
+    "yauzl": {
+      "version": "2.10.0",
+      "resolved": "https://registry.npmjs.org/yauzl/-/yauzl-2.10.0.tgz",
+      "integrity": "sha1-x+sXyT4RLLEIb6bY5R+wZnt5pfk=",
+      "dev": true,
+      "requires": {
+        "buffer-crc32": "~0.2.3",
+        "fd-slicer": "~1.1.0"
+      }
     }
   }
 }
diff --git a/package.json b/package.json
index 23b3e49..0f49904 100644
--- a/package.json
+++ b/package.json
@@ -1,6 +1,6 @@
 {
   "name": "@author.io/shell",
-  "version": "1.5.0",
+  "version": "1.5.1",
   "description": "A micro-framework for creating CLI-like experiences. This supports Node.js and browsers.",
   "main": "src/index.js",
   "scripts": {
diff --git a/src/base.js b/src/base.js
index bcdd803..9c5da3a 100644
--- a/src/base.js
+++ b/src/base.js
@@ -17,6 +17,13 @@ export default class Base {
   #middleware = new Middleware()
   #trailer = new Middleware()
   #commonflags = {}
+  #display = {
+    // These are all null, representing they're NOT configured.
+    Default: null,
+    Options: null,
+    MultipleValues: null,
+    Required: null
+  }
   #hasCustomDefaultHandler = false
   #defaultHandler = function (meta) {
     if (this.parent !== null && this.parent.hasCustomDefaultHandler) {
@@ -72,7 +79,7 @@ export default class Base {
     }
 
     if (Array.isArray(cfg.arguments)) {
-      this.#arguments = cfg.arguments
+      this.#arguments = new Set(cfg.arguments)
     }
 
     this.#name = (cfg.name || 'unknown').trim().split(/\s+/)[0]
@@ -113,12 +120,6 @@ export default class Base {
     }
 
     Object.defineProperties(this, {
-      __arguments: {
-        enumerable: false,
-        get() {
-          return this.#arguments
-        }
-      },
       __processors: {
         enumerable: false,
         get() {
@@ -182,6 +183,26 @@ export default class Base {
             throw new Error('Invalid trailer: ' + code.toString())
           }
         }
+      },
+      initializeHelpAnnotations: {
+        enumerable: false,
+        configurable: false,
+        writable: false,
+        value: cfg => {
+          if (cfg.hasOwnProperty('describeDefault') && typeof cfg.describeDefault === 'boolean') {
+            console.log('HERE')
+            this.#display.Default = cfg.describeDefault
+          }
+          if (cfg.hasOwnProperty('describeOptions') && typeof cfg.describeOptions === 'boolean') {
+            this.#display.Options = cfg.describeOptions
+          }
+          if (cfg.hasOwnProperty('describeMultipleValues') && typeof cfg.describeMultipleValues === 'boolean') {
+            this.#display.MultipleValues = cfg.describeMultipleValues
+          }
+          if (cfg.hasOwnProperty('describeRequired') && typeof cfg.describeRequired === 'boolean') {
+            this.#display.Required = cfg.describeRequired
+          }
+        }
       }
     })
   }
@@ -211,6 +232,40 @@ export default class Base {
     this.#formattedDefaultHelp.width = this.#width
   }
 
+  describeHelp (attr, prop) {
+    if (this.#display[prop] !== null) {
+      return this.#display[prop]
+    }
+
+    if (this instanceof Command) {
+      if (this.shell[attr] !== null) {
+        return this.shell[attr]
+      }
+      
+      if (this.parent !== null) {
+        return this.parent[attr]
+      }
+    }
+
+    return true
+  }
+
+  get describeDefault () {
+    return this.describeHelp('describeDefault', 'Default')
+  }
+
+  get describeOptions () {
+    return this.describeHelp('describeOptions', 'Options')
+  }
+
+  get describeMultipleValues () {
+    return this.describeHelp('describeMultipleValues', 'MultipleValues')
+  }
+
+  get describeRequired () {
+    return this.describeHelp('describeRequired', 'Required')
+  }
+
   get usage() {
     if (this.#customUsage !== null) {
       return typeof this.#customUsage === 'function' ? this.#customUsage() : this.#customUsage
diff --git a/src/command.js b/src/command.js
index 782f420..11e7c9f 100644
--- a/src/command.js
+++ b/src/command.js
@@ -38,6 +38,8 @@ export default class Command extends Base {
       cfg.trailer.forEach(code => this.initializeTrailer(code))
     }
 
+    this.initializeHelpAnnotations(cfg)
+
     this.#fn = cfg.handler
     this.#oid = Symbol(((cfg.name || cfg.usage) || cfg.pattern) || 'command')
     this.#pattern = cfg.pattern || /[\s\S]+/i
@@ -91,6 +93,10 @@ export default class Command extends Base {
       'subcommands',
       'defaultHandler',
       'disableHelp',
+      'describeDefault',
+      'describeOptions',
+      'describeMultipleValues',
+      'describeRequired',
       'flags',
       'alias',
       'aliases',
diff --git a/src/format.js b/src/format.js
index 976a686..8b40547 100644
--- a/src/format.js
+++ b/src/format.js
@@ -29,7 +29,7 @@ class Formatter {
     
     if (this.#data instanceof Command) {
       const aliases = this.#data.aliases
-      const out = [`${this.#data.commandroot}${aliases.length > 0 ? '|' + aliases.join('|') : ''}${this.#data.__flagConfig.size > 0 ? ' [FLAGS]' : ''}${this.#data.__arguments.size > 0 ? ' ' + Array.from(this.#data.__arguments).map(i => '<' + i + '>').join(', ') : ''}`]
+      const out = [`${this.#data.commandroot}${aliases.length > 0 ? '|' + aliases.join('|') : ''}${this.#data.__flagConfig.size > 0 ? ' [FLAGS]' : ''}${this.#data.arguments.size > 0 ? ' ' + Array.from(this.#data.arguments).map(i => '<' + i + '>').join(', ') : ''}`]
       
       if (desc.trim().length > 0 && out !== desc) {
         out.push(new Table([[desc.trim().replace(/\n/gi, '\n  ')]], null, null, this.#tableWidth, [2, 0, 1, 1]).output)
@@ -37,7 +37,7 @@ class Formatter {
 
       return out.join('\n')
     } else if (this.#data instanceof Shell) {
-      return `${this.#data.name}${this.#data.__processors.size > 0 ? ' [COMMAND]' : ''}\n${desc.trim().length > 0 ? new Table([[desc.trim().replace(/\n/gi, '\n  ')]], null, null, this.#tableWidth, [2, 0, 1, 1]).output : ''}${this.#data.__arguments.size > 0 ? ' ' + Array.from(this.#data.__arguments).map(i => '[' + i + ']').join(', ') : ''}\n`.trim()
+      return `${this.#data.name}${this.#data.__processors.size > 0 ? ' [COMMAND]' : ''}\n${desc.trim().length > 0 ? new Table([[desc.trim().replace(/\n/gi, '\n  ')]], null, null, this.#tableWidth, [2, 0, 1, 1]).output : ''}${this.#data.arguments.size > 0 ? ' ' + Array.from(this.#data.arguments).map(i => '[' + i + ']').join(', ') : ''}\n`.trim()
     }
 
     return ''
@@ -49,12 +49,33 @@ class Formatter {
     if (this.#data instanceof Command) {
       const flags = this.#data.__flagConfig
       const rows = []
-      
+
       if (flags.size > 0) {
         flags.forEach((cfg, flag) => {
           let aliases = Array.from(cfg.aliases||cfg.alias||[])
           aliases = aliases.length === 0 ? '' : '[' + aliases.map(a => `-${a}`).join(', ') + ']'
-          rows.push(['-' + flag, aliases || '', cfg.description || ''])
+          
+          let dsc = [cfg.description || '']
+
+          if (cfg.hasOwnProperty('options') && this.#data.describeOptions) {
+            dsc.push(`Options: ${cfg.options.join(', ')}.`)
+          }
+          
+          if (cfg.hasOwnProperty('allowMultipleValues') && cfg.allowMultipleValues === true && this.#data.describeMultipleValues) {
+            dsc.push('Can be used multiple times.')
+          }
+
+          if (cfg.hasOwnProperty('default') && this.#data.describeDefault) {
+            dsc.push(`(Default: ${cfg.default.toString()})`)
+          }
+
+          if (cfg.hasOwnProperty('required') && cfg.required === true && this.#data.describeRequired) {
+            dsc.unshift('Required.')
+          }
+
+          dsc = dsc.join(' ').trim()
+          
+          rows.push(['-' + flag, aliases || '', dsc || ''])
         })
       }
 
diff --git a/src/shell.js b/src/shell.js
index 193d4b4..999a718 100644
--- a/src/shell.js
+++ b/src/shell.js
@@ -23,6 +23,8 @@ export default class Shell extends Base {
   constructor (cfg = { maxhistory: 100 }) {
     super(cfg)
 
+    this.initializeHelpAnnotations(cfg)
+
     this.__commonflags = cfg.commonflags || {}
 
     if (cfg.hasOwnProperty('use') && Array.isArray(cfg.use)) {