diff --git a/Library/Homebrew/cask/upgrade.rb b/Library/Homebrew/cask/upgrade.rb
index 6e60b2415a..b6a077de52 100644
--- a/Library/Homebrew/cask/upgrade.rb
+++ b/Library/Homebrew/cask/upgrade.rb
@@ -42,9 +42,16 @@ module Cask
 
       greedy = true if Homebrew::EnvConfig.upgrade_greedy?
 
+      greedy_casks = if (upgrade_greedy_casks = Homebrew::EnvConfig.upgrade_greedy_casks.presence)
+        upgrade_greedy_casks.split
+      else
+        []
+      end
+
       outdated_casks = if casks.empty?
         Caskroom.casks(config: Config.from_args(args)).select do |cask|
-          cask.outdated?(greedy:, greedy_latest:,
+          cask_greedy = greedy || greedy_casks.include?(cask.token)
+          cask.outdated?(greedy: cask_greedy, greedy_latest:,
                          greedy_auto_updates:)
         end
       else
@@ -78,7 +85,7 @@ module Cask
 
       return false if outdated_casks.empty?
 
-      if casks.empty? && !greedy
+      if casks.empty? && !greedy && greedy_casks.empty?
         if !greedy_auto_updates && !greedy_latest
           ohai "Casks with 'auto_updates true' or 'version :latest' " \
                "will not be upgraded; pass `--greedy` to upgrade them."
diff --git a/Library/Homebrew/env_config.rb b/Library/Homebrew/env_config.rb
index 1157ad0780..d44acc84b8 100644
--- a/Library/Homebrew/env_config.rb
+++ b/Library/Homebrew/env_config.rb
@@ -486,6 +486,10 @@ module Homebrew
         description: "If set, pass `--greedy` to all cask upgrade commands.",
         boolean:     true,
       },
+      HOMEBREW_UPGRADE_GREEDY_CASKS:             {
+        description: "A space-separated list of casks. Homebrew will act as " \
+                     "if `--greedy` was passed when upgrading any cask on this list.",
+      },
       HOMEBREW_VERBOSE:                          {
         description: "If set, always assume `--verbose` when running commands.",
         boolean:     true,
diff --git a/Library/Homebrew/sorbet/rbi/dsl/homebrew/env_config.rbi b/Library/Homebrew/sorbet/rbi/dsl/homebrew/env_config.rbi
index bc71d5feb7..2e4bfabb92 100644
--- a/Library/Homebrew/sorbet/rbi/dsl/homebrew/env_config.rbi
+++ b/Library/Homebrew/sorbet/rbi/dsl/homebrew/env_config.rbi
@@ -307,6 +307,9 @@ module Homebrew::EnvConfig
     sig { returns(T::Boolean) }
     def upgrade_greedy?; end
 
+    sig { returns(T.nilable(::String)) }
+    def upgrade_greedy_casks; end
+
     sig { returns(T::Boolean) }
     def verbose?; end