diff --git a/Library/Homebrew/cmd/outdated.rb b/Library/Homebrew/cmd/outdated.rb
index 72170324a6..acaac7b45f 100644
--- a/Library/Homebrew/cmd/outdated.rb
+++ b/Library/Homebrew/cmd/outdated.rb
@@ -48,6 +48,8 @@ module Homebrew
 
       sig { override.void }
       def run
+        @greedy = Homebrew::EnvConfig.upgrade_greedy? || args.greedy?
+
         case json_version(args.json)
         when :v1
           odie "`brew outdated --json=v1` is no longer supported. Use brew outdated --json=v2 instead."
@@ -118,7 +120,7 @@ module Homebrew
           else
             c = formula_or_cask
 
-            puts c.outdated_info(args.greedy?, verbose?, false, args.greedy_latest?, args.greedy_auto_updates?)
+            puts c.outdated_info(@greedy, verbose?, false, args.greedy_latest?, args.greedy_auto_updates?)
           end
         end
       end
@@ -143,7 +145,7 @@ module Homebrew
           else
             c = formula_or_cask
 
-            c.outdated_info(args.greedy?, verbose?, true, args.greedy_latest?, args.greedy_auto_updates?)
+            c.outdated_info(@greedy, verbose?, true, args.greedy_latest?, args.greedy_auto_updates?)
           end
         end
       end
@@ -193,7 +195,7 @@ 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outdated?(fetch_head: args.fetch_HEAD?)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outdated?(greedy: args.greedy?, greedy_latest: args.greedy_latest?,
+            formula_or_cask.outdated?(greedy: @greedy, greedy_latest: args.greedy_latest?,
                                       greedy_auto_updates: args.greedy_auto_updates?)
           end
         end
diff --git a/Library/Homebrew/env_config.rb b/Library/Homebrew/env_config.rb
index d77c1c5399..7a54f55fc1 100644
--- a/Library/Homebrew/env_config.rb
+++ b/Library/Homebrew/env_config.rb
@@ -436,7 +436,7 @@ module Homebrew
         boolean:     true,
       },
       HOMEBREW_UPGRADE_GREEDY:                   {
-        description: "If set, pass `--greedy` to all cask upgrade commands.",
+        description: "If set, pass `--greedy` to all cask upgrade commands and `brew outdated`.",
         boolean:     true,
       },
       HOMEBREW_VERBOSE:                          {