diff --git a/IPython/config/application.py b/IPython/config/application.py
index 04dbe86..05022e0 100644
--- a/IPython/config/application.py
+++ b/IPython/config/application.py
@@ -33,7 +33,11 @@ from IPython.utils.traitlets import (
     Unicode, List, Int, Enum, Dict, Instance
 )
 from IPython.utils.importstring import import_item
-from IPython.utils.text import indent
+from IPython.utils.text import indent, wrap_paragraphs, dedent
+
+#-----------------------------------------------------------------------------
+# function for re-wrapping a helpstring
+#-----------------------------------------------------------------------------
 
 #-----------------------------------------------------------------------------
 # Descriptions for the various sections
@@ -44,6 +48,8 @@ Flags are command-line arguments passed as '--<flag>'.
 These take no parameters, unlike regular key-value arguments.
 They are typically used for setting boolean flags, or enabling
 modes that involve setting multiple options together.
+
+Flags *always* begin with '--', never just one '-'.
 """.strip() # trim newlines of front and back
 
 alias_description = """
@@ -104,10 +110,18 @@ class Application(SingletonConfigurable):
     # this must be a dict of two-tuples, the first element being the Config/dict
     # and the second being the help string for the flag
     flags = Dict()
+    def _flags_changed(self, name, old, new):
+        """ensure flags dict is valid"""
+        for key,value in new.iteritems():
+            assert len(value) == 2, "Bad flag: %r:%s"%(key,value)
+            assert isinstance(value[0], (dict, Config)), "Bad flag: %r:%s"%(key,value)
+            assert isinstance(value[1], basestring), "Bad flag: %r:%s"%(key,value)
+        
     
     # subcommands for launching other applications
     # if this is not empty, this will be a parent Application
-    # this must be a dict of two-tuples, the first element being the application class/import string
+    # this must be a dict of two-tuples, 
+    # the first element being the application class/import string
     # and the second being the help string for the subcommand
     subcommands = Dict()
     # parse_command_line will initialize a subapp, if requested
@@ -123,11 +137,6 @@ class Application(SingletonConfigurable):
         # options.
         self.classes.insert(0, self.__class__)
         
-        # ensure self.flags dict is valid
-        for key,value in self.flags.iteritems():
-            assert len(value) == 2, "Bad flag: %r:%s"%(key,value)
-            assert isinstance(value[0], (dict, Config)), "Bad flag: %r:%s"%(key,value)
-            assert isinstance(value[1], basestring), "Bad flag: %r:%s"%(key,value)
         self.init_logging()
 
     def _config_changed(self, name, old, new):
@@ -170,14 +179,16 @@ class Application(SingletonConfigurable):
         self.log.setLevel(new)
     
     def print_alias_help(self):
-        """print the alias part of the help"""
+        """Print the alias part of the help."""
         if not self.aliases:
             return
         
         lines = ['Aliases']
         lines.append('-'*len(lines[0]))
-        lines.append(self.alias_description)
         lines.append('')
+        for p in wrap_paragraphs(self.alias_description):
+            lines.append(p)
+            lines.append('')
         
         classdict = {}
         for cls in self.classes:
@@ -197,23 +208,25 @@ class Application(SingletonConfigurable):
         print '\n'.join(lines)
     
     def print_flag_help(self):
-        """print the flag part of the help"""
+        """Print the flag part of the help."""
         if not self.flags:
             return
         
         lines = ['Flags']
         lines.append('-'*len(lines[0]))
-        lines.append(self.flag_description)
         lines.append('')
+        for p in wrap_paragraphs(self.flag_description):
+            lines.append(p)
+            lines.append('')
         
         for m, (cfg,help) in self.flags.iteritems():
             lines.append('--'+m)
-            lines.append(indent(help.strip(), flatten=True))
+            lines.append(indent(dedent(help.strip())))
         lines.append('')
         print '\n'.join(lines)
     
     def print_subcommands(self):
-        """print the subcommand part of the help"""
+        """Print the subcommand part of the help."""
         if not self.subcommands:
             return
         
@@ -222,14 +235,14 @@ class Application(SingletonConfigurable):
         for subc, (cls,help) in self.subcommands.iteritems():
             lines.append("%s : %s"%(subc, cls))
             if help:
-                lines.append(indent(help.strip(), flatten=True))
+                lines.append(indent(dedent(help.strip())))
         lines.append('')
         print '\n'.join(lines)
     
     def print_help(self, classes=False):
         """Print the help for each Configurable class in self.classes.
         
-        If classes=False (the default), only flags and aliases are printed
+        If classes=False (the default), only flags and aliases are printed.
         """
         self.print_subcommands()
         self.print_flag_help()
@@ -239,8 +252,10 @@ class Application(SingletonConfigurable):
             if self.classes:
                 print "Class parameters"
                 print "----------------"
-                print self.keyvalue_description
                 print
+                for p in wrap_paragraphs(self.keyvalue_description):
+                    print p
+                    print
         
             for cls in self.classes:
                 cls.class_print_help()
@@ -251,8 +266,9 @@ class Application(SingletonConfigurable):
 
     def print_description(self):
         """Print the application description."""
-        print self.description
-        print
+        for p in wrap_paragraphs(self.description):
+            print p
+            print
 
     def print_version(self):
         """Print the version string."""
@@ -269,7 +285,7 @@ class Application(SingletonConfigurable):
         self.config = newconfig
     
     def initialize_subcommand(self, subc, argv=None):
-        """Initialize a subcommand with argv"""
+        """Initialize a subcommand with argv."""
         subapp,help = self.subcommands.get(subc)
         
         if isinstance(subapp, basestring):
@@ -330,7 +346,7 @@ class Application(SingletonConfigurable):
 #-----------------------------------------------------------------------------
 
 def boolean_flag(name, configurable, set_help='', unset_help=''):
-    """helper for building basic --trait, --no-trait flags
+    """Helper for building basic --trait, --no-trait flags.
     
     Parameters
     ----------
@@ -360,3 +376,4 @@ def boolean_flag(name, configurable, set_help='', unset_help=''):
     setter = {cls : {trait : True}}
     unsetter = {cls : {trait : False}}
     return {name : (setter, set_help), 'no-'+name : (unsetter, unset_help)}
+
diff --git a/IPython/config/configurable.py b/IPython/config/configurable.py
index 433195f..94a7595 100755
--- a/IPython/config/configurable.py
+++ b/IPython/config/configurable.py
@@ -21,12 +21,12 @@ Authors:
 # Imports
 #-----------------------------------------------------------------------------
 
-from copy import deepcopy
 import datetime
+from copy import deepcopy
 
 from loader import Config
 from IPython.utils.traitlets import HasTraits, Instance
-from IPython.utils.text import indent
+from IPython.utils.text import indent, wrap_paragraphs
 
 
 #-----------------------------------------------------------------------------
@@ -51,7 +51,7 @@ class Configurable(HasTraits):
     created = None
 
     def __init__(self, **kwargs):
-        """Create a conigurable given a config config.
+        """Create a configurable given a config config.
 
         Parameters
         ----------
@@ -153,27 +153,31 @@ class Configurable(HasTraits):
     
     @classmethod
     def class_get_trait_help(cls, trait):
-        """Get the help string for a single """
+        """Get the help string for a single trait."""
         lines = []
         header = "%s.%s : %s" % (cls.__name__, trait.name, trait.__class__.__name__)
+        lines.append(header)
         try:
             dvr = repr(trait.get_default_value())
         except Exception:
             dvr = None # ignore defaults we can't construct
         if dvr is not None:
-            header += ' [default: %s]'%dvr
-        lines.append(header)
+            if len(dvr) > 64:
+                dvr = dvr[:61]+'...'
+            lines.append(indent('Default: %s'%dvr, 4))
+        if 'Enum' in trait.__class__.__name__:
+            # include Enum choices
+            lines.append(indent('Choices: %r'%(trait.values,)))
         
         help = trait.get_metadata('help')
         if help is not None:
-            lines.append(indent(help.strip(), flatten=True))
-        if 'Enum' in trait.__class__.__name__:
-            # include Enum choices
-            lines.append(indent('Choices: %r'%(trait.values,), flatten=True))
+            help = '\n'.join(wrap_paragraphs(help, 76))
+            lines.append(indent(help, 4))
         return '\n'.join(lines)
 
     @classmethod
     def class_print_help(cls):
+        """Get the help string for a single trait and print it."""
         print cls.class_get_help()
 
 
diff --git a/IPython/utils/text.py b/IPython/utils/text.py
index 9370da8..d0e3387 100644
--- a/IPython/utils/text.py
+++ b/IPython/utils/text.py
@@ -19,6 +19,7 @@ import __main__
 import os
 import re
 import shutil
+import textwrap
 from string import Formatter
 
 from IPython.external.path import path
@@ -520,6 +521,58 @@ def format_screen(strng):
     strng = par_re.sub('',strng)
     return strng
 
+def dedent(text):
+    """Equivalent of textwrap.dedent that ignores unindented first line.
+    
+    This means it will still dedent strings like:
+    '''foo
+    is a bar
+    '''
+    
+    For use in wrap_paragraphs.
+    """
+    
+    if text.startswith('\n'):
+        # text starts with blank line, don't ignore the first line
+        return textwrap.dedent(text)
+    
+    # split first line
+    splits = text.split('\n',1)
+    if len(splits) == 1:
+        # only one line
+        return textwrap.dedent(text)
+    
+    first, rest = splits
+    # dedent everything but the first line
+    rest = textwrap.dedent(rest)
+    return '\n'.join([first, rest])
+
+def wrap_paragraphs(text, ncols=80):
+    """Wrap multiple paragraphs to fit a specified width.
+    
+    This is equivalent to textwrap.wrap, but with support for multiple
+    paragraphs, as separated by empty lines.
+    
+    Returns
+    -------
+    
+    list of complete paragraphs, wrapped to fill `ncols` columns.
+    """
+    paragraph_re = re.compile(r'\n(\s*\n)+', re.MULTILINE)
+    text = dedent(text).strip()
+    paragraphs = paragraph_re.split(text)[::2] # every other entry is space
+    out_ps = []
+    indent_re = re.compile(r'\n\s+', re.MULTILINE)
+    for p in paragraphs:
+        # presume indentation that survives dedent is meaningful formatting, 
+        # so don't fill unless text is flush.
+        if indent_re.search(p) is None:
+            # wrap paragraph
+            p = textwrap.fill(p, ncols)
+        out_ps.append(p)
+    return out_ps
+    
+
 
 class EvalFormatter(Formatter):
     """A String Formatter that allows evaluation of simple expressions.