diff --git a/Library/Homebrew/Gemfile.lock b/Library/Homebrew/Gemfile.lock
index 0b78e4ceadd7d..97085e7ce01c3 100644
--- a/Library/Homebrew/Gemfile.lock
+++ b/Library/Homebrew/Gemfile.lock
@@ -14,7 +14,7 @@ GEM
       bindata (~> 2)
     erubi (1.13.0)
     hana (1.3.7)
-    json (2.7.6)
+    json (2.8.1)
     json_schemer (2.3.0)
       bigdecimal
       hana (~> 1.3)
diff --git a/Library/Homebrew/cmd/outdated.rb b/Library/Homebrew/cmd/outdated.rb
index 17232e8dd4a24..2c7e7000d1622 100644
--- a/Library/Homebrew/cmd/outdated.rb
+++ b/Library/Homebrew/cmd/outdated.rb
@@ -62,13 +62,14 @@ def run
           end
 
           json = {
-            "formulae" => json_info(formulae),
-            "casks"    => json_info(casks),
+            formulae: json_info(formulae),
+            casks:    json_info(casks),
           }
-          puts JSON.pretty_generate(json)
+          # json v2.8.1 is inconsistent it how it renders empty arrays,
+          # so we use `[]` for consistency:
+          puts JSON.pretty_generate(json).gsub(/\[\n\n\s*\]/, "[]")
 
           outdated = formulae + casks
-
         else
           outdated = if args.formula?
             outdated_formulae
@@ -170,10 +171,7 @@ def json_version(version)
           "v1" => :v1,
           "v2" => :v2,
         }
-
-        raise UsageError, "invalid JSON version: #{version}" unless version_hash.include?(version)
-
-        version_hash[version]
+        version_hash.fetch(version) { raise UsageError, "invalid JSON version: #{version}" }
       end
 
       sig { returns(T::Array[Formula]) }
diff --git a/Library/Homebrew/test/support/fixtures/cask/everything.json b/Library/Homebrew/test/support/fixtures/cask/everything.json
index d290bd45d16ea..60c1abab72c16 100644
--- a/Library/Homebrew/test/support/fixtures/cask/everything.json
+++ b/Library/Homebrew/test/support/fixtures/cask/everything.json
@@ -1,9 +1,7 @@
 {
   "token": "everything",
   "full_token": "everything",
-  "old_tokens": [
-
-  ],
+  "old_tokens": [],
   "tap": "homebrew/cask",
   "name": [
     "Everything"
diff --git a/Library/Homebrew/vendor/bundle/bundler/setup.rb b/Library/Homebrew/vendor/bundle/bundler/setup.rb
index b91a71108ced5..fb67b203c8d1b 100644
--- a/Library/Homebrew/vendor/bundle/bundler/setup.rb
+++ b/Library/Homebrew/vendor/bundle/bundler/setup.rb
@@ -47,8 +47,8 @@ def self.extension_api_version
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/elftools-1.3.1/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/erubi-1.13.0/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/hana-1.3.7/lib")
-$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/extensions/arm64-darwin-20/#{Gem.extension_api_version}/json-2.7.6")
-$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/json-2.7.6/lib")
+$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/extensions/arm64-darwin-20/#{Gem.extension_api_version}/json-2.8.1")
+$:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/json-2.8.1/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/regexp_parser-2.9.2/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/simpleidn-0.2.3/lib")
 $:.unshift File.expand_path("#{__dir__}/../#{RUBY_ENGINE}/#{Gem.ruby_api_version}/gems/json_schemer-2.3.0/lib")