diff --git a/src/Stackctl/DirectoryOption.hs b/src/Stackctl/DirectoryOption.hs
--- a/src/Stackctl/DirectoryOption.hs
+++ b/src/Stackctl/DirectoryOption.hs
@@ -30,7 +30,7 @@
 envDirectoryOption :: Env.Parser Env.Error DirectoryOption
 envDirectoryOption =
   Env.var (Env.str <=< Env.nonempty) "DIRECTORY"
-    $ Env.help "Operate on specifications in this directory"
+    $ Env.help directoryHelp
 
 directoryOption :: Parser DirectoryOption
 directoryOption =
@@ -39,6 +39,10 @@
       [ short 'd'
       , long "directory"
       , metavar "PATH"
-      , help "Operate on specifications in PATH"
+      , help directoryHelp
       , action "directory"
       ]
+
+directoryHelp :: String
+directoryHelp =
+  "Use the stack collection located at PATH (default: current working directory)"
diff --git a/src/Stackctl/Subcommand.hs b/src/Stackctl/Subcommand.hs
--- a/src/Stackctl/Subcommand.hs
+++ b/src/Stackctl/Subcommand.hs
@@ -10,6 +10,8 @@
 
 import qualified Env
 import Options.Applicative
+import Prettyprinter (pretty, vsep)
+import Prettyprinter.Util (reflow)
 import Stackctl.AWS (handlingServiceError)
 import Stackctl.AutoSSO
 import Stackctl.CLI
@@ -46,7 +48,9 @@
   (options, act) <-
     applyEnv
       <$> Env.parse (Env.header $ unpack title) parseEnv
-      <*> execParser (withInfo title $ (,) <$> parseCLI <*> subparser sp)
+      <*> customExecParser
+        (prefs helpShowGlobals)
+        (withInfo title $ (,) <$> parseCLI <*> subparser sp)
 
   act options
  where
@@ -78,4 +82,15 @@
     $ f subOptions
 
 withInfo :: Text -> Parser a -> ParserInfo a
-withInfo d p = info (p <**> helper) $ progDesc (unpack d) <> fullDesc
+withInfo d p =
+  info (p <**> helper)
+    $ progDescDoc
+    $ Just
+    $ vsep
+      [ pretty d
+      , ""
+      , reflow
+          $ "By default, this will operate on the entire stack collection. To"
+            <> " operate on a specific stack or set of stacks, use the --filter"
+            <> " argument to filter the collection by file path."
+      ]
diff --git a/stackctl.cabal b/stackctl.cabal
--- a/stackctl.cabal
+++ b/stackctl.cabal
@@ -1,6 +1,6 @@
 cabal-version:   1.18
 name:            stackctl
-version:         1.7.3.5
+version:         1.7.3.6
 license:         MIT
 license-file:    LICENSE
 copyright:       2022 Renaissance Learning Inc
@@ -113,6 +113,7 @@
         monad-logger >=0.3.41,
         mtl >=2.3.1,
         optparse-applicative >=0.18.1.0,
+        prettyprinter >=1.7.1,
         resourcet >=1.3.0,
         rio >=0.1.22.0,
         semigroups >=0.20,