diff --git a/Library/Homebrew/cask/upgrade.rb b/Library/Homebrew/cask/upgrade.rb
index 17c38f43bee6e..41c52954f9960 100644
--- a/Library/Homebrew/cask/upgrade.rb
+++ b/Library/Homebrew/cask/upgrade.rb
@@ -42,6 +42,8 @@ def self.upgrade_casks(
 
       quarantine = true if quarantine.nil?
 
+      greedy = true if Homebrew::EnvConfig.upgrade_greedy?
+
       outdated_casks = if casks.empty?
         Caskroom.casks(config: Config.from_args(args)).select do |cask|
           cask.outdated?(greedy: greedy, greedy_latest: greedy_latest,
diff --git a/Library/Homebrew/env_config.rb b/Library/Homebrew/env_config.rb
index 3d0d0db091d42..94a3ca7f96ff2 100644
--- a/Library/Homebrew/env_config.rb
+++ b/Library/Homebrew/env_config.rb
@@ -344,6 +344,10 @@ module EnvConfig
         description: "If set, use Pry for the `brew irb` command.",
         boolean:     true,
       },
+      HOMEBREW_UPGRADE_GREEDY:                   {
+        description: "If set, pass `--greedy` to all cask upgrade commands.",
+        boolean:     true,
+      },
       HOMEBREW_SIMULATE_MACOS_ON_LINUX:          {
         description: "If set, running Homebrew on Linux will simulate certain macOS code paths. This is useful " \
                      "when auditing macOS formulae while on Linux.",
diff --git a/Library/Homebrew/env_config.rbi b/Library/Homebrew/env_config.rbi
index bf67f9c624f5c..f52d381c760ec 100644
--- a/Library/Homebrew/env_config.rbi
+++ b/Library/Homebrew/env_config.rbi
@@ -229,6 +229,9 @@ module Homebrew::EnvConfig
   sig { returns(T::Boolean) }
   def self.update_to_tag?; end
 
+  sig { returns(T::Boolean) }
+  def self.upgrade_greedy?; end
+
   sig { returns(T::Boolean) }
   def self.verbose?; end