diff --git a/Library/Homebrew/cask/cask.rb b/Library/Homebrew/cask/cask.rb
index cb789407cb..2e1856d471 100644
--- a/Library/Homebrew/cask/cask.rb
+++ b/Library/Homebrew/cask/cask.rb
@@ -113,16 +113,19 @@ module Cask
       @caskroom_path ||= Caskroom.path.join(token)
     end
 
-    def outdated?(greedy: false)
-      !outdated_versions(greedy: greedy).empty?
+    def outdated?(greedy: false, greedy_latest: false, greedy_auto_updates: false)
+      !outdated_versions(greedy: greedy, greedy_latest: greedy_latest,
+                         greedy_auto_updates: greedy_auto_updates).empty?
     end
 
-    def outdated_versions(greedy: false)
+    def outdated_versions(greedy: false, greedy_latest: false, greedy_auto_updates: false)
       # special case: tap version is not available
       return [] if version.nil?
 
-      if greedy
+      if greedy || (greedy_latest && greedy_auto_updates) || (greedy_auto_updates && auto_updates)
         return versions if version.latest?
+      elsif greedy_latest && version.latest?
+        return versions
       elsif auto_updates
         return []
       end
@@ -137,10 +140,11 @@ module Cask
       installed.reject { |v| v == version }
     end
 
-    def outdated_info(greedy, verbose, json)
+    def outdated_info(greedy, verbose, json, greedy_latest, greedy_auto_updates)
       return token if !verbose && !json
 
-      installed_versions = outdated_versions(greedy: greedy).join(", ")
+      installed_versions = outdated_versions(greedy: greedy, greedy_latest: greedy_latest,
+                                             greedy_auto_updates: greedy_auto_updates).join(", ")
 
       if json
         {
diff --git a/Library/Homebrew/cask/cmd/upgrade.rb b/Library/Homebrew/cask/cmd/upgrade.rb
index 1ba58f831a..650a43d2f2 100644
--- a/Library/Homebrew/cask/cmd/upgrade.rb
+++ b/Library/Homebrew/cask/cmd/upgrade.rb
@@ -19,6 +19,12 @@ module Cask
         [:switch, "--greedy", {
           description: "Also include casks with `auto_updates true` or `version :latest`.",
         }],
+        [:switch, "--greedy-latest", {
+          description: "Also include casks with `version :latest`.",
+        }],
+        [:switch, "--greedy-auto-updates", {
+          description: "Also include casks with `auto_updates true`.",
+        }],
       ].freeze
 
       sig { returns(Homebrew::CLI::Parser) }
@@ -40,30 +46,34 @@ module Cask
         verbose = ($stdout.tty? || args.verbose?) && !args.quiet?
         self.class.upgrade_casks(
           *casks,
-          force:          args.force?,
-          greedy:         args.greedy?,
-          dry_run:        args.dry_run?,
-          binaries:       args.binaries?,
-          quarantine:     args.quarantine?,
-          require_sha:    args.require_sha?,
-          skip_cask_deps: args.skip_cask_deps?,
-          verbose:        verbose,
-          args:           args,
+          force:               args.force?,
+          greedy:              args.greedy?,
+          greedy_latest:       args.greedy_latest?,
+          greedy_auto_updates: args.greedy_auto_updates?,
+          dry_run:             args.dry_run?,
+          binaries:            args.binaries?,
+          quarantine:          args.quarantine?,
+          require_sha:         args.require_sha?,
+          skip_cask_deps:      args.skip_cask_deps?,
+          verbose:             verbose,
+          args:                args,
         )
       end
 
       sig {
         params(
-          casks:          Cask,
-          args:           Homebrew::CLI::Args,
-          force:          T.nilable(T::Boolean),
-          greedy:         T.nilable(T::Boolean),
-          dry_run:        T.nilable(T::Boolean),
-          skip_cask_deps: T.nilable(T::Boolean),
-          verbose:        T.nilable(T::Boolean),
-          binaries:       T.nilable(T::Boolean),
-          quarantine:     T.nilable(T::Boolean),
-          require_sha:    T.nilable(T::Boolean),
+          casks:               Cask,
+          args:                Homebrew::CLI::Args,
+          force:               T.nilable(T::Boolean),
+          greedy:              T.nilable(T::Boolean),
+          greedy_latest:       T.nilable(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),
+          binaries:            T.nilable(T::Boolean),
+          quarantine:          T.nilable(T::Boolean),
+          require_sha:         T.nilable(T::Boolean),
         ).returns(T::Boolean)
       }
       def self.upgrade_casks(
@@ -71,6 +81,8 @@ module Cask
         args:,
         force: false,
         greedy: false,
+        greedy_latest: false,
+        greedy_auto_updates: false,
         dry_run: false,
         skip_cask_deps: false,
         verbose: false,
@@ -83,7 +95,8 @@ module Cask
 
         outdated_casks = if casks.empty?
           Caskroom.casks(config: Config.from_args(args)).select do |cask|
-            cask.outdated?(greedy: greedy)
+            cask.outdated?(greedy: greedy, greedy_latest: args.greedy_latest?,
+                           greedy_auto_updates: args.greedy_auto_updates?)
           end
         else
           casks.select do |cask|
@@ -107,7 +120,16 @@ 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."
+          if !args.greedy_auto_updates? && !args.greedy_latest?
+            ohai "Casks with 'auto_updates true' or 'version :latest'
+            will not be upgraded; pass `--greedy` to upgrade them."
+          end
+          if args.greedy_auto_updates? && !args.greedy_latest?
+            ohai "Casks with 'version :latest' will not be upgraded; pass `--greedy-latest` to upgrade them."
+          end
+          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."
+          end
         end
 
         verb = dry_run ? "Would upgrade" : "Upgrading"
diff --git a/Library/Homebrew/cmd/outdated.rb b/Library/Homebrew/cmd/outdated.rb
index af7fb7a915..da9575f623 100644
--- a/Library/Homebrew/cmd/outdated.rb
+++ b/Library/Homebrew/cmd/outdated.rb
@@ -37,7 +37,13 @@ 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 true`."
 
       conflicts "--quiet", "--verbose", "--json"
       conflicts "--formula", "--cask"
@@ -119,7 +125,7 @@ module Homebrew
       else
         c = formula_or_cask
 
-        puts c.outdated_info(args.greedy?, verbose?, false)
+        puts c.outdated_info(args.greedy?, verbose?, false, args.greedy_latest?, args.greedy_auto_updates?)
       end
     end
   end
@@ -144,7 +150,8 @@ 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
@@ -194,7 +201,8 @@ module Homebrew
       if formula_or_cask.is_a?(Formula)
         formula_or_cask.outdated?(fetch_head: args.fetch_HEAD?)
       else
-        formula_or_cask.outdated?(greedy: args.greedy?)
+        formula_or_cask.outdated?(greedy: args.greedy?, greedy_latest: args.greedy_latest?,
+                                  greedy_auto_updates: args.greedy_auto_updates?)
       end
     end
   end