diff --git a/amanuensis/__main__.py b/amanuensis/__main__.py
index 300fe21..278c22f 100644
--- a/amanuensis/__main__.py
+++ b/amanuensis/__main__.py
@@ -45,6 +45,9 @@ def repl(args):
 			except Exception as e:
 				traceback.print_exc()
 
+def process_doc(docstring):
+	return '\n'.join([line.strip() for line in (docstring or "").strip().splitlines()])
+
 def get_parser(valid_commands):
 	# Set up the top-level parser.
 	parser = argparse.ArgumentParser(
@@ -89,7 +92,7 @@ def get_parser(valid_commands):
 	for name, func in valid_commands.items():
 		# Create the subparser, set the docstring as the description.
 		cmd = subp.add_parser(name,
-			description=func.__doc__,
+			description=process_doc(func.__doc__),
 			formatter_class=argparse.RawDescriptionHelpFormatter)
 		# Delegate subparser setup to the command.
 		func(cmd)
diff --git a/amanuensis/cli/__init__.py b/amanuensis/cli/__init__.py
index 8505028..8460fed 100644
--- a/amanuensis/cli/__init__.py
+++ b/amanuensis/cli/__init__.py
@@ -38,22 +38,25 @@ def user_commands(commands={}):
 def get_commands():
 	return {**server_commands(), **lexicon_commands(), **user_commands()}
 
+def cmd_desc(func):
+	return ((func.__doc__ or "").strip() or '\n').splitlines()[0]
+
 def describe_commands():
 	longest = max(map(len, server_commands().keys()))
 	server_desc = "General commands:\n{}\n".format("\n".join([
-		" {1:<{0}} : {2}".format(longest, name, func.__doc__ or "")
+		" {1:<{0}} : {2}".format(longest, name, cmd_desc(func))
 		for name, func in server_commands().items()
 	]))
 
 	longest = max(map(len, lexicon_commands().keys()))
 	lexicon_desc = "Lexicon commands:\n{}\n".format("\n".join([
-		" {1:<{0}} : {2}".format(longest, name, func.__doc__ or "")
+		" {1:<{0}} : {2}".format(longest, name, cmd_desc(func))
 		for name, func in lexicon_commands().items()
 	]))
 
 	longest = max(map(len, user_commands().keys()))
 	user_desc = "User commands:\n{}\n".format("\n".join([
-		" {1:<{0}} : {2}".format(longest, name, func.__doc__ or "")
+		" {1:<{0}} : {2}".format(longest, name, cmd_desc(func))
 		for name, func in user_commands().items()
 	]))
 
diff --git a/amanuensis/cli/server.py b/amanuensis/cli/server.py
index 5af0c15..ee1043a 100644
--- a/amanuensis/cli/server.py
+++ b/amanuensis/cli/server.py
@@ -4,7 +4,13 @@ CONFIG_GET_ROOT_VALUE = object()
 
 @add_argument("--update", action="store_true", help="Refresh an existing config directory")
 def command_init(args):
-	"""Initialize a config directory at the directory given by --config-dir"""
+	"""
+	Initialize a config directory at --config-dir
+
+	A clean config directory will contain a config.json, a
+	pidfile, a lexicon config directory, and a user config
+	directory.
+	"""
 	from collections import OrderedDict
 	import fcntl
 	import json
@@ -58,7 +64,12 @@ def command_init(args):
 
 @no_argument
 def command_generate_secret(args):
-	"""Generate a secret key for Flask"""
+	"""
+	Generate a Flask secret key
+
+	The Flask server will not run unless a secret key has
+	been generated.
+	"""
 	import os
 
 	import config
@@ -71,7 +82,12 @@ def command_generate_secret(args):
 @add_argument("-a", "--address", default="127.0.0.1")
 @add_argument("-p", "--port", default="5000")
 def command_run(args):
-	"""Run the default Flask server"""
+	"""
+	Run the default Flask server
+	
+	The default Flask server is not secure, and should
+	only be used for development.
+	"""
 	import server
 	import config
 
@@ -85,7 +101,12 @@ def command_run(args):
 @add_argument("--set", metavar=("PATHSPEC", "VALUE"), dest="set",
 	nargs=2, help="Set the value of a config key")
 def command_config(args):
-	"""Interact with the global config"""
+	"""
+	Interact with the global config
+
+	PATHSPEC is a path into the config object formatted as
+	a dot-separated sequence of keys.
+	"""
 	import json
 	import config