diff --git a/CHANGELOG.md b/CHANGELOG.md
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -1,3 +1,13 @@
+## Version 0.15.1.0 (12 Sep 2019)
+
+- Improve printing of brief descriptions for parsers.
+  Previously, the logical structure of the parser,
+  such as alternative groups and segments which must
+  be defined together, did not influence the layout of
+  the brief description. This could lead to some help
+  texts being difficult to read.  Now, we use nesting
+  and forced line breaks to help improve readability.
+
 ## Version 0.15.0.0 (05 Jul 2019)
 
 - Add support for GHC 8.8.1.
@@ -11,7 +21,7 @@
 - Improve rendering of complex nested parse structures.
   Previously, brackets and parenthesis did not respect
   whether or not options had to be defined together.
-  Now the parse tree is more accurately represeted in
+  Now the parse tree is more accurately represented in
   the help text.
 
 - Add `helpLongEquals` modifier, which will change how
diff --git a/README.md b/README.md
--- a/README.md
+++ b/README.md
@@ -5,8 +5,8 @@
 [![Hackage-Deps][hackage-deps-png]][hackage-deps]
 
 optparse-applicative is a haskell library for parsing options on
-the command line, providing a powerful [applicative] interface
-for composing these options.
+the command line, and providing a powerful [applicative] interface
+for composing them.
 
 optparse-applicative takes care of reading and validating the
 arguments passed to the command line, handling and reporting errors,
diff --git a/optparse-applicative.cabal b/optparse-applicative.cabal
--- a/optparse-applicative.cabal
+++ b/optparse-applicative.cabal
@@ -1,5 +1,5 @@
 name:                optparse-applicative
-version:             0.15.0.0
+version:             0.15.1.0
 synopsis:            Utilities and combinators for parsing command line options
 description:
     optparse-applicative is a haskell library for parsing options
diff --git a/src/Options/Applicative/Help/Core.hs b/src/Options/Applicative/Help/Core.hs
--- a/src/Options/Applicative/Help/Core.hs
+++ b/src/Options/Applicative/Help/Core.hs
@@ -112,7 +112,7 @@
       , descHidden = False }
 
 -- | Wrap a doc in parentheses or brackets if required.
-wrap :: AltNodeType ->  (Chunk Doc, Wrapping) -> Chunk Doc
+wrap :: AltNodeType -> (Chunk Doc, Wrapping) -> Chunk Doc
 wrap altnode (chunk, wrapping)
   | altnode == MarkDefault
   = fmap brackets chunk
@@ -130,15 +130,17 @@
   = (foldr ((<</>>) . wrap NoDefault . foldTree) mempty xs, Bare)
 foldTree (AltNode b xs)
   = (\x -> (x, Bare))
+  . fmap groupOrNestLine
   . wrap b
   . alt_node
   . filter (not . isEmpty . fst)
   . map foldTree $ xs
     where
+
   alt_node :: [(Chunk Doc, Wrapping)] -> (Chunk Doc, Wrapping)
   alt_node [n] = n
   alt_node ns = (\y -> (y, Wrapped))
-              . foldr (chunked (\x y -> x </> char '|' </> y) . wrap NoDefault) mempty
+              . foldr (chunked altSep . wrap NoDefault) mempty
               $ ns
 
 -- | Generate a full help text for a parser.
diff --git a/src/Options/Applicative/Help/Pretty.hs b/src/Options/Applicative/Help/Pretty.hs
--- a/src/Options/Applicative/Help/Pretty.hs
+++ b/src/Options/Applicative/Help/Pretty.hs
@@ -1,10 +1,56 @@
 module Options.Applicative.Help.Pretty
   ( module Text.PrettyPrint.ANSI.Leijen
   , (.$.)
+  , groupOrNestLine
+  , altSep
   ) where
 
-import Text.PrettyPrint.ANSI.Leijen hiding ((<$>), (<>), columns)
+import           Control.Applicative
+import           Data.Semigroup ((<>))
+
+import           Text.PrettyPrint.ANSI.Leijen hiding ((<$>), (<>), columns)
+import           Text.PrettyPrint.ANSI.Leijen.Internal (Doc (..), flatten)
 import qualified Text.PrettyPrint.ANSI.Leijen as PP
 
+import           Prelude
+
 (.$.) :: Doc -> Doc -> Doc
 (.$.) = (PP.<$>)
+
+
+-- | Apply the function if we're not at the
+--   start of our nesting level.
+ifNotAtRoot :: (Doc -> Doc) -> Doc -> Doc
+ifNotAtRoot f doc =
+  Nesting $ \i ->
+    Column $ \j ->
+      if i == j
+        then doc
+        else f doc
+
+
+-- | Render flattened text on this line, or start
+--   a new line before rendering any text.
+--
+--   This will also nest subsequent lines in the
+--   group.
+groupOrNestLine :: Doc -> Doc
+groupOrNestLine =
+  Union
+    <$> flatten
+    <*> ifNotAtRoot (line <>) . nest 2
+
+
+-- | Separate items in an alternative with a pipe.
+--
+--   If the first document and the pipe don't fit
+--   on the line, then mandatorily flow the next entry
+--   onto the following line.
+--
+--   The (<//>) softbreak ensures that if the document
+--   does fit on the line, there is at least a space,
+--   but it's possible for y to still appear on the
+--   next line.
+altSep :: Doc -> Doc -> Doc
+altSep x y =
+  group (x <+> char '|' <> line) <//> y