diff --git a/apps/cat.cpp b/apps/cat.cpp
index 5ac525fb..7236fbf9 100644
--- a/apps/cat.cpp
+++ b/apps/cat.cpp
@@ -30,6 +30,7 @@ Result<int> luna_main(int argc, char** argv)
     StringView filename;
 
     os::ArgumentParser parser;
+    parser.add_description("Concatenate files to standard output."_sv);
     parser.add_positional_argument(filename, "file"_sv, "-"_sv);
     Vector<StringView> extra_files = TRY(parser.parse(argc, argv));
 
diff --git a/apps/chmod.cpp b/apps/chmod.cpp
index 8440c8bf..e1f3f206 100644
--- a/apps/chmod.cpp
+++ b/apps/chmod.cpp
@@ -9,6 +9,7 @@ int main(int argc, char** argv)
     StringView path;
 
     os::ArgumentParser parser;
+    parser.add_description("Change the permissions of a file."_sv);
     parser.add_positional_argument(mode_string, "mode"_sv, true);
     parser.add_positional_argument(path, "path"_sv, true);
     parser.parse(argc, argv);
diff --git a/apps/chown.cpp b/apps/chown.cpp
index cf7e64c2..36f88b7e 100644
--- a/apps/chown.cpp
+++ b/apps/chown.cpp
@@ -9,6 +9,7 @@ int main(int argc, char** argv)
     StringView path;
 
     os::ArgumentParser parser;
+    parser.add_description("Change the owner and group of a file."_sv);
     parser.add_positional_argument(user, "user"_sv, true);
     parser.add_positional_argument(path, "path"_sv, true);
     parser.parse(argc, argv);
diff --git a/apps/date.cpp b/apps/date.cpp
index 3019f69d..e20a2d5b 100644
--- a/apps/date.cpp
+++ b/apps/date.cpp
@@ -10,7 +10,9 @@ int main(int argc, char** argv)
     StringView date;
 
     os::ArgumentParser parser;
-    parser.add_value_argument(date, 'd', "date"_sv, true);
+    parser.add_description("Display the current (or another) date and time."_sv);
+    parser.add_value_argument(date, 'd', "date"_sv, true,
+                              "the UNIX timestamp to display instead of the current time"_sv);
     parser.parse(argc, argv);
 
     time_t now;
diff --git a/apps/edit.cpp b/apps/edit.cpp
index 1bfe0c9e..88039dcb 100644
--- a/apps/edit.cpp
+++ b/apps/edit.cpp
@@ -9,6 +9,7 @@ Result<int> luna_main(int argc, char** argv)
     StringView pathname;
 
     os::ArgumentParser parser;
+    parser.add_description("Edit a file using basic line-based shell editing."_sv);
     parser.add_positional_argument(pathname, "path"_sv, true);
     parser.parse(argc, argv);
 
diff --git a/apps/ls.cpp b/apps/ls.cpp
index 2b848022..4053a9e9 100644
--- a/apps/ls.cpp
+++ b/apps/ls.cpp
@@ -12,9 +12,10 @@ Result<int> luna_main(int argc, char** argv)
     bool show_almost_all { false };
 
     os::ArgumentParser parser;
+    parser.add_description("List files contained in a directory (defaults to '.', the current directory)"_sv);
     parser.add_positional_argument(pathname, "directory"_sv, "."_sv);
-    parser.add_switch_argument(show_all, 'a', "all"_sv);
-    parser.add_switch_argument(show_almost_all, 'A', "almost-all"_sv);
+    parser.add_switch_argument(show_all, 'a', "all"_sv, "also list hidden files (whose filename begins with a dot)"_sv);
+    parser.add_switch_argument(show_almost_all, 'A', "almost-all"_sv, "list all files except '.' and '..'"_sv);
     parser.parse(argc, argv);
 
     DIR* dp = opendir(pathname.chars());
diff --git a/apps/mkdir.cpp b/apps/mkdir.cpp
index 8927e660..e4a1ef8d 100644
--- a/apps/mkdir.cpp
+++ b/apps/mkdir.cpp
@@ -30,9 +30,11 @@ Result<int> luna_main(int argc, char** argv)
     bool recursive;
 
     os::ArgumentParser parser;
+    parser.add_description("Create directories."_sv);
     parser.add_positional_argument(path, "path"_sv, true);
     parser.add_positional_argument(mode_string, "mode"_sv, "755"_sv);
-    parser.add_switch_argument(recursive, 'p', "parents"_sv);
+    parser.add_switch_argument(recursive, 'p', "parents"_sv,
+                               "if parent directories do not exist, create them as well"_sv);
     parser.parse(argc, argv);
 
     mode_t mode = (mode_t)parse_unsigned_integer(mode_string.chars(), nullptr, 8);
diff --git a/apps/rm.cpp b/apps/rm.cpp
index 096336e1..494c89a2 100644
--- a/apps/rm.cpp
+++ b/apps/rm.cpp
@@ -7,8 +7,10 @@ Result<int> luna_main(int argc, char** argv)
     bool recursive;
 
     os::ArgumentParser parser;
+    parser.add_description("Remove a path from the file system."_sv);
     parser.add_positional_argument(path, "path"_sv, true);
-    parser.add_switch_argument(recursive, 'r', "recursive"_sv);
+    parser.add_switch_argument(recursive, 'r', "recursive"_sv,
+                               "remove a directory recursively (by default, rm removes only empty directories)"_sv);
     parser.parse(argc, argv);
 
     if (!recursive) TRY(os::FileSystem::remove(path));
diff --git a/apps/sh.cpp b/apps/sh.cpp
index 0e16bcc8..42a73c63 100644
--- a/apps/sh.cpp
+++ b/apps/sh.cpp
@@ -37,8 +37,9 @@ Result<int> luna_main(int argc, char** argv)
     SharedPtr<File> input_file;
 
     os::ArgumentParser parser;
+    parser.add_description("The Luna system's command shell."_sv);
     parser.add_positional_argument(path, "path"_sv, "-"_sv);
-    parser.add_value_argument(command, 'c', "command"_sv, true);
+    parser.add_value_argument(command, 'c', "command"_sv, true, "execute a single command and then exit"_sv);
     parser.parse(argc, argv);
 
     if (!command.is_empty()) TRY(execute_command(command));
diff --git a/apps/su.cpp b/apps/su.cpp
index f699dc0e..60c990fc 100644
--- a/apps/su.cpp
+++ b/apps/su.cpp
@@ -62,6 +62,7 @@ Result<int> luna_main(int argc, char** argv)
     }
 
     os::ArgumentParser parser;
+    parser.add_description("Switch to a different user."_sv);
     parser.add_positional_argument(name, "name"_sv, true);
     parser.parse(argc, argv);
 
diff --git a/libos/include/os/ArgumentParser.h b/libos/include/os/ArgumentParser.h
index 8be7aa56..5f04382a 100644
--- a/libos/include/os/ArgumentParser.h
+++ b/libos/include/os/ArgumentParser.h
@@ -7,15 +7,19 @@ namespace os
     class ArgumentParser
     {
       public:
-        ArgumentParser() = default;
+        ArgumentParser(bool add_help = true);
+
+        void add_description(StringView description);
 
         Result<void> add_positional_argument(StringView& out, StringView name, bool required);
         Result<void> add_positional_argument(StringView& out, StringView name, StringView fallback);
 
-        Result<void> add_switch_argument(bool& out, char short_flag, StringView long_flag);
+        Result<void> add_switch_argument(bool& out, char short_flag, StringView long_flag, StringView help = {});
 
-        Result<void> add_value_argument(StringView& out, char short_flag, StringView long_flag, bool value_required);
-        Result<void> add_value_argument(StringView& out, char short_flag, StringView long_flag, StringView fallback);
+        Result<void> add_value_argument(StringView& out, char short_flag, StringView long_flag, bool value_required,
+                                        StringView help = {});
+        Result<void> add_value_argument(StringView& out, char short_flag, StringView long_flag, StringView fallback,
+                                        StringView help = {});
 
         Result<Vector<StringView>> parse(int argc, char* const* argv);
 
@@ -33,6 +37,7 @@ namespace os
             bool* out;
             char short_flag;
             StringView long_flag;
+            StringView help;
         };
 
         struct ValueArgument
@@ -42,10 +47,17 @@ namespace os
             StringView long_flag;
             bool required;
             StringView fallback;
+            StringView help;
         };
 
+        Result<void> usage(StringView program_name);
+        void short_usage(StringView program_name);
+
         Vector<PositionalArgument> m_positional_args;
         Vector<SwitchArgument> m_switch_args;
         Vector<ValueArgument> m_value_args;
+        StringView m_description = {};
+        bool m_add_short_help_flag { false };
+        bool m_add_long_help_flag { false };
     };
 }
diff --git a/libos/src/ArgumentParser.cpp b/libos/src/ArgumentParser.cpp
index 09022fdd..f7a0ea0f 100644
--- a/libos/src/ArgumentParser.cpp
+++ b/libos/src/ArgumentParser.cpp
@@ -1,9 +1,19 @@
+#include <luna/StringBuilder.h>
 #include <os/ArgumentParser.h>
 #include <stdio.h>
 #include <stdlib.h>
 
 namespace os
 {
+    ArgumentParser::ArgumentParser(bool add_help) : m_add_short_help_flag(add_help), m_add_long_help_flag(add_help)
+    {
+    }
+
+    void ArgumentParser::add_description(StringView description)
+    {
+        m_description = description;
+    }
+
     Result<void> ArgumentParser::add_positional_argument(StringView& out, StringView name, bool required)
     {
         PositionalArgument arg { &out, name, required, {} };
@@ -18,25 +28,34 @@ namespace os
         return m_positional_args.try_append(move(arg));
     }
 
-    Result<void> ArgumentParser::add_switch_argument(bool& out, char short_flag, StringView long_flag)
+    Result<void> ArgumentParser::add_switch_argument(bool& out, char short_flag, StringView long_flag, StringView help)
     {
-        SwitchArgument arg { &out, short_flag, long_flag };
+        SwitchArgument arg { &out, short_flag, long_flag, help };
+
+        if (short_flag == 'h') m_add_short_help_flag = false;
+        if (long_flag == "help"_sv) m_add_long_help_flag = false;
 
         return m_switch_args.try_append(move(arg));
     }
 
     Result<void> ArgumentParser::add_value_argument(StringView& out, char short_flag, StringView long_flag,
-                                                    bool value_required)
+                                                    bool value_required, StringView help)
     {
-        ValueArgument arg { &out, short_flag, long_flag, value_required, {} };
+        ValueArgument arg { &out, short_flag, long_flag, value_required, {}, help };
+
+        if (short_flag == 'h') m_add_short_help_flag = false;
+        if (long_flag == "help"_sv) m_add_long_help_flag = false;
 
         return m_value_args.try_append(move(arg));
     }
 
     Result<void> ArgumentParser::add_value_argument(StringView& out, char short_flag, StringView long_flag,
-                                                    StringView fallback)
+                                                    StringView fallback, StringView help)
     {
-        ValueArgument arg { &out, short_flag, long_flag, false, fallback };
+        ValueArgument arg { &out, short_flag, long_flag, false, fallback, help };
+
+        if (short_flag == 'h') m_add_short_help_flag = false;
+        if (long_flag == "help"_sv) m_add_long_help_flag = false;
 
         return m_value_args.try_append(move(arg));
     }
@@ -87,6 +106,8 @@ namespace os
 
                     bool found = false;
 
+                    if (m_add_long_help_flag && flag == "help"_sv) { TRY(usage(program_name)); }
+
                     for (const auto& current : m_switch_args)
                     {
                         if (current.long_flag == flag)
@@ -111,7 +132,7 @@ namespace os
                     if (found) continue;
 
                     fprintf(stderr, "%s: unrecognized option '%s'\n", program_name.chars(), arg.chars());
-                    exit(1);
+                    short_usage(program_name);
                 }
                 else if (looks_like_short_flag(arg))
                 {
@@ -122,6 +143,8 @@ namespace os
                         char c = flags[j];
                         bool found = false;
 
+                        if (m_add_short_help_flag && c == 'h') { TRY(usage(program_name)); }
+
                         // Last flag, this could be a value flag
                         if (j + 1 == flags.length())
                         {
@@ -156,7 +179,7 @@ namespace os
                         if (found) continue;
 
                         fprintf(stderr, "%s: invalid option -- '%c'\n", program_name.chars(), c);
-                        exit(1);
+                        short_usage(program_name);
                     }
 
                     continue;
@@ -179,7 +202,7 @@ namespace os
             {
                 fprintf(stderr, "%s: option '--%s' requires an argument\n", program_name.chars(),
                         current_value_argument->long_flag.chars());
-                exit(1);
+                short_usage(program_name);
             }
             else { *current_value_argument->out = current_value_argument->fallback; }
         }
@@ -190,11 +213,86 @@ namespace os
             if (arg.required)
             {
                 fprintf(stderr, "%s: required argument '%s' not provided\n", program_name.chars(), arg.name.chars());
-                exit(1);
+                short_usage(program_name);
             }
             else { *arg.out = arg.fallback; }
         }
 
         return leftovers;
     }
+
+    Result<void> ArgumentParser::usage(StringView program_name)
+    {
+        StringBuilder sb;
+        TRY(sb.format("Usage: %s <options>"_sv, program_name.chars()));
+
+        for (const auto& arg : m_positional_args)
+        {
+            if (arg.required) { TRY(sb.format(" %s", arg.name.chars())); }
+            else { TRY(sb.format(" [%s]", arg.name.chars())); }
+        }
+
+        TRY(sb.add('\n'));
+
+        auto usage_line = TRY(sb.string());
+        fputs(usage_line.chars(), stdout);
+
+        if (!m_description.is_empty()) { puts(m_description.chars()); }
+
+        if (m_switch_args.size() || m_value_args.size())
+        {
+            putchar('\n');
+            puts("Options:");
+        }
+
+        for (const auto& arg : m_switch_args)
+        {
+            if (arg.long_flag.is_empty())
+            {
+                if (arg.short_flag == ' ') continue;
+
+                printf("  -%-25c %s\n", arg.short_flag, arg.help.chars());
+            }
+            else if (arg.short_flag == ' ') { printf("      --%-20s %s\n", arg.long_flag.chars(), arg.help.chars()); }
+            else { printf("  -%c, --%-20s %s\n", arg.short_flag, arg.long_flag.chars(), arg.help.chars()); }
+        }
+
+        for (const auto& arg : m_value_args)
+        {
+            StringView value_name;
+            if (arg.required) value_name = "VALUE"_sv;
+            else
+                value_name = "[VALUE]"_sv;
+
+            int field_size = 20 - (int)(arg.long_flag.length() + 1);
+            if (field_size < 0) field_size = 0;
+
+            if (arg.long_flag.is_empty())
+            {
+                if (arg.short_flag == ' ') continue;
+
+                printf("  -%c %-20s %s\n", arg.short_flag, value_name.chars(), arg.help.chars());
+            }
+            else if (arg.short_flag == ' ')
+            {
+                printf("      --%s %-*s %s\n", arg.long_flag.chars(), field_size, value_name.chars(), arg.help.chars());
+            }
+            else
+            {
+                printf("  -%c, --%s %-*s %s\n", arg.short_flag, arg.long_flag.chars(), field_size, value_name.chars(),
+                       arg.help.chars());
+            }
+        }
+
+        exit(0);
+    }
+
+    void ArgumentParser::short_usage(StringView program_name)
+    {
+        if (m_add_short_help_flag || m_add_long_help_flag)
+            fprintf(stderr, "Try running '%s %s' for more information.\n", program_name.chars(),
+                    m_add_long_help_flag ? "--help" : "-h");
+
+        exit(1);
+    }
 }