diff --git a/Library/Homebrew/cask/cmd/upgrade.rb b/Library/Homebrew/cask/cmd/upgrade.rb
index 346edbedd0..43e9b6dcd7 100644
--- a/Library/Homebrew/cask/cmd/upgrade.rb
+++ b/Library/Homebrew/cask/cmd/upgrade.rb
@@ -48,8 +48,8 @@ module Cask
           *casks,
           force:               args.force?,
           greedy:              args.greedy?,
-          greedy_latest:       args.greedy_latest,
-          greedy_auto_updates: args.greedy_auto_updates,
+          greedy_latest:       args.greedy_latest?,
+          greedy_auto_updates: args.greedy_auto_updates?,
           dry_run:             args.dry_run?,
           binaries:            args.binaries?,
           quarantine:          args.quarantine?,
@@ -67,7 +67,7 @@ module Cask
           force:               T.nilable(T::Boolean),
           greedy:              T.nilable(T::Boolean),
           greedy_latest:       T.nilable(T::Boolean),
-          greedy_auto_updates: T.nilabel(T::Boolean),
+          greedy_auto_updates: T.nilable(T::Boolean),
           dry_run:             T.nilable(T::Boolean),
           skip_cask_deps:      T.nilable(T::Boolean),
           verbose:             T.nilable(T::Boolean),
@@ -120,7 +120,9 @@ module Cask
         return false if outdated_casks.empty?
 
         if casks.empty? && !greedy
-          ohai "Casks with 'auto_updates' or 'version :latest' will not be upgraded; pass `--greedy` to upgrade them."
+          ohai "Casks with 'auto_updates true' or 'version :latest' will not be upgraded; pass `--greedy` to upgrade them." if !args.greedy_auto_updates? && !args.greedy_latest?
+          ohai "Casks with 'version :latest' will not be upgraded; pass `--greedy-latest` to upgrade them." if args.greedy_auto_updates? && !args.greedy_latest?
+          ohai "Casks with 'auto_updates true' will not be upgraded; pass `--greedy-auto-updates` to upgrade them." if !args.greedy_auto_updates? && args.greedy_latest?
         end
 
         verb = dry_run ? "Would upgrade" : "Upgrading"
diff --git a/Library/Homebrew/cmd/outdated.rb b/Library/Homebrew/cmd/outdated.rb
index 22c86a26de..5dd535fe80 100644
--- a/Library/Homebrew/cmd/outdated.rb
+++ b/Library/Homebrew/cmd/outdated.rb
@@ -36,13 +36,13 @@ module Homebrew
                           "formula is outdated. Otherwise, the repository's HEAD will only be checked for "\
                           "updates when a new stable or development version has been released."
       switch "--greedy",
-             description: "Print outdated casks with `auto_updates` or `version :latest`."
+             description: "Print outdated casks with `auto_updates true` or `version :latest`."
 
       switch "--greedy-latest",
              description: "Print outdated casks including those with `version :latest`."
 
       switch "--greedy-auto-updates",
-             description: "Print outdated casks including those with `auto_updates`."
+             description: "Print outdated casks including those with `auto_updates true`."
 
       conflicts "--quiet", "--verbose", "--json"
       conflicts "--formula", "--cask"
@@ -147,7 +147,8 @@ module Homebrew
       else
         c = formula_or_cask
 
-        c.outdated_info(args.greedy?, verbose?, true)
+        c.outdated_info(args.greedy?, verbose?, true, greedy_latest: args.greedy_latest?,
+          greedy_auto_updates: args.greedy_auto_updates?)
       end
     end
   end