diff --git a/Library/.rubocop.yml b/Library/.rubocop.yml
index f43fbe54c0..c94b248a3b 100644
--- a/Library/.rubocop.yml
+++ b/Library/.rubocop.yml
@@ -26,6 +26,9 @@ Layout/CaseIndentation:
 Layout/EmptyLineBetweenDefs:
   AllowAdjacentOneLineDefs: true
 
+Layout/EndAlignment:
+  EnforcedStyleAlignWith: variable
+
 Layout/IndentArray:
   EnforcedStyle: special_inside_parentheses
 
@@ -52,9 +55,6 @@ Lint/AmbiguousBlockAssociation:
 Lint/AssignmentInCondition:
   Enabled: false
 
-Lint/EndAlignment:
-  EnforcedStyleAlignWith: variable
-
 # so many of these in formulae and can't be autocorrected
 Lint/ParenthesesAsGroupedExpression:
   Enabled: false
@@ -205,7 +205,10 @@ Style/TernaryParentheses:
   EnforcedStyle: require_parentheses_when_complex
 
 # makes diffs nicer
-Style/TrailingCommaInLiteral:
+Style/TrailingCommaInArrayLiteral:
+  EnforcedStyleForMultiline: comma
+
+Style/TrailingCommaInHashLiteral:
   EnforcedStyleForMultiline: comma
 
 Style/TrailingCommaInArguments:
@@ -215,6 +218,10 @@ Style/TrailingCommaInArguments:
 Naming/VariableNumber:
   Enabled: false
 
+# doesn't make sense for Homebrew/brew but does for taps
+Naming/UncommunicativeMethodParamName:
+  Enabled: true
+
 Style/WordArray:
   MinSize: 4
 
diff --git a/Library/Homebrew/.rubocop.yml b/Library/Homebrew/.rubocop.yml
index e0089e0500..58b911ca9f 100644
--- a/Library/Homebrew/.rubocop.yml
+++ b/Library/Homebrew/.rubocop.yml
@@ -68,6 +68,10 @@ Naming/PredicateName:
     - 'compat/**/*'
   NameWhitelist: is_32_bit?, is_64_bit?
 
+# f meaning formulae is pretty standard
+Naming/UncommunicativeMethodParamName:
+  Enabled: false
+
 Style/BlockDelimiters:
   Exclude:
     - '**/*_spec.rb'
diff --git a/Library/Homebrew/cask/lib/hbc/cask_loader.rb b/Library/Homebrew/cask/lib/hbc/cask_loader.rb
index 74c39176d3..640282ec36 100644
--- a/Library/Homebrew/cask/lib/hbc/cask_loader.rb
+++ b/Library/Homebrew/cask/lib/hbc/cask_loader.rb
@@ -1,3 +1,5 @@
+require "uri"
+
 module Hbc
   module CaskLoader
     class FromContentLoader
diff --git a/Library/Homebrew/cmd/gist-logs.rb b/Library/Homebrew/cmd/gist-logs.rb
index ab81a017e2..c30ee85cd9 100644
--- a/Library/Homebrew/cmd/gist-logs.rb
+++ b/Library/Homebrew/cmd/gist-logs.rb
@@ -113,14 +113,14 @@ module Homebrew
     url = "https://api.github.com/gists"
     data = { "public" => true, "files" => files, "description" => description }
     scopes = GitHub::CREATE_GIST_SCOPES
-    GitHub.open(url, data: data, scopes: scopes)["html_url"]
+    GitHub.open_api(url, data: data, scopes: scopes)["html_url"]
   end
 
   def create_issue(repo, title, body)
     url = "https://api.github.com/repos/#{repo}/issues"
     data = { "title" => title, "body" => body }
     scopes = GitHub::CREATE_ISSUE_SCOPES
-    GitHub.open(url, data: data, scopes: scopes)["html_url"]
+    GitHub.open_api(url, data: data, scopes: scopes)["html_url"]
   end
 
   def gist_logs
diff --git a/Library/Homebrew/cmd/install.rb b/Library/Homebrew/cmd/install.rb
index e1e4712ea1..bacdb18f02 100644
--- a/Library/Homebrew/cmd/install.rb
+++ b/Library/Homebrew/cmd/install.rb
@@ -344,7 +344,7 @@ module Homebrew
   rescue FormulaInstallationAlreadyAttemptedError
     # We already attempted to install f as part of the dependency tree of
     # another formula. In that case, don't generate an error, just move on.
-    return
+    nil
   rescue CannotInstallFormulaError => e
     ofail e.message
   end
diff --git a/Library/Homebrew/cmd/reinstall.rb b/Library/Homebrew/cmd/reinstall.rb
index 7c62d8092a..420c08dfe8 100644
--- a/Library/Homebrew/cmd/reinstall.rb
+++ b/Library/Homebrew/cmd/reinstall.rb
@@ -47,7 +47,7 @@ module Homebrew
     fi.install
     fi.finish
   rescue FormulaInstallationAlreadyAttemptedError
-    return
+    nil
   rescue Exception # rubocop:disable Lint/RescueException
     ignore_interrupts { restore_backup(keg, keg_was_linked) }
     raise
diff --git a/Library/Homebrew/cmd/update-report.rb b/Library/Homebrew/cmd/update-report.rb
index 2c4d3de0c5..d241d17b06 100644
--- a/Library/Homebrew/cmd/update-report.rb
+++ b/Library/Homebrew/cmd/update-report.rb
@@ -13,7 +13,7 @@ module Homebrew
   module_function
 
   def update_preinstall_header
-    @header_already_printed ||= begin
+    @update_preinstall_header ||= begin
       ohai "Auto-updated Homebrew!" if ARGV.include?("--preinstall")
       true
     end
diff --git a/Library/Homebrew/cmd/upgrade.rb b/Library/Homebrew/cmd/upgrade.rb
index 1446025805..4e6dd04631 100644
--- a/Library/Homebrew/cmd/upgrade.rb
+++ b/Library/Homebrew/cmd/upgrade.rb
@@ -139,7 +139,7 @@ module Homebrew
   rescue FormulaInstallationAlreadyAttemptedError
     # We already attempted to upgrade f as part of the dependency tree of
     # another formula. In that case, don't generate an error, just move on.
-    return
+    nil
   rescue CannotInstallFormulaError => e
     ofail e
   rescue BuildError => e
diff --git a/Library/Homebrew/constants.rb b/Library/Homebrew/constants.rb
index 9514320abe..77c69f3e43 100644
--- a/Library/Homebrew/constants.rb
+++ b/Library/Homebrew/constants.rb
@@ -1,5 +1,5 @@
 # frozen_string_literal: true
 
 # RuboCop version used for `brew style` and `brew cask style`
-HOMEBREW_RUBOCOP_VERSION = "0.52.1"
-HOMEBREW_RUBOCOP_CASK_VERSION = "~> 0.16.0" # has to be updated when RuboCop version changes
+HOMEBREW_RUBOCOP_VERSION = "0.53.0"
+HOMEBREW_RUBOCOP_CASK_VERSION = "~> 0.17.0" # has to be updated when RuboCop version changes
diff --git a/Library/Homebrew/diagnostic.rb b/Library/Homebrew/diagnostic.rb
index 79f5b2f1d0..1b779f226b 100644
--- a/Library/Homebrew/diagnostic.rb
+++ b/Library/Homebrew/diagnostic.rb
@@ -966,7 +966,7 @@ module Homebrew
           Putting non-prefixed coreutils in your path can cause gmp builds to fail.
         EOS
       rescue FormulaUnavailableError
-        return
+        nil
       end
 
       def check_for_non_prefixed_findutils
@@ -981,7 +981,7 @@ module Homebrew
           Putting non-prefixed findutils in your path can cause python builds to fail.
         EOS
       rescue FormulaUnavailableError
-        return
+        nil
       end
 
       def check_for_pydistutils_cfg_in_home
diff --git a/Library/Homebrew/download_strategy.rb b/Library/Homebrew/download_strategy.rb
index e85661d76d..6e750806f0 100644
--- a/Library/Homebrew/download_strategy.rb
+++ b/Library/Homebrew/download_strategy.rb
@@ -604,7 +604,7 @@ class GitHubPrivateRepositoryReleaseDownloadStrategy < GitHubPrivateRepositoryDo
 
   def fetch_release_metadata
     release_url = "https://api.github.com/repos/#{@owner}/#{@repo}/releases/tags/#{@tag}"
-    GitHub.open(release_url)
+    GitHub.open_api(release_url)
   end
 end
 
diff --git a/Library/Homebrew/extend/os/linux/system_config.rb b/Library/Homebrew/extend/os/linux/system_config.rb
index cf01765623..47eca7697e 100644
--- a/Library/Homebrew/extend/os/linux/system_config.rb
+++ b/Library/Homebrew/extend/os/linux/system_config.rb
@@ -31,7 +31,7 @@ class SystemConfig
       return "N/A" unless CoreTap.instance.installed?
       Formulary.factory(formula).linked_version || "N/A"
     rescue FormulaUnavailableError
-      return "N/A"
+      "N/A"
     end
 
     def dump_verbose_config(out = $stdout)
diff --git a/Library/Homebrew/formula_versions.rb b/Library/Homebrew/formula_versions.rb
index c10c69e674..67edba9c5e 100644
--- a/Library/Homebrew/formula_versions.rb
+++ b/Library/Homebrew/formula_versions.rb
@@ -44,7 +44,7 @@ class FormulaVersions
     # continue walking the history
     ohai "#{e} in #{name} at revision #{rev}", e.backtrace if ARGV.debug?
   rescue FormulaUnavailableError
-    return
+    nil
   ensure
     Homebrew.raise_deprecation_exceptions = false
   end
diff --git a/Library/Homebrew/rubocops/extend/formula_cop.rb b/Library/Homebrew/rubocops/extend/formula_cop.rb
index e53c02a449..2c20e62dec 100644
--- a/Library/Homebrew/rubocops/extend/formula_cop.rb
+++ b/Library/Homebrew/rubocops/extend/formula_cop.rb
@@ -4,6 +4,8 @@ require_relative "../../extend/string"
 module RuboCop
   module Cop
     class FormulaCop < Cop
+      include RangeHelp
+
       attr_accessor :file_path
       @registry = Cop.registry
 
diff --git a/Library/Homebrew/sandbox.rb b/Library/Homebrew/sandbox.rb
index ea74fae098..e59e2a5500 100644
--- a/Library/Homebrew/sandbox.rb
+++ b/Library/Homebrew/sandbox.rb
@@ -108,10 +108,10 @@ class Sandbox
 
     unless logs.empty?
       if @logfile
-        log = open(@logfile, "w")
-        log.write logs
-        log.write "\nWe use time to filter sandbox log. Therefore, unrelated logs may be recorded.\n"
-        log.close
+        File.open(@logfile, "w") do |log|
+          log.write logs
+          log.write "\nWe use time to filter sandbox log. Therefore, unrelated logs may be recorded.\n"
+        end
       end
 
       if @failed && ARGV.verbose?
diff --git a/Library/Homebrew/tab.rb b/Library/Homebrew/tab.rb
index aa0208d51a..0fed724a8d 100644
--- a/Library/Homebrew/tab.rb
+++ b/Library/Homebrew/tab.rb
@@ -326,8 +326,8 @@ class Tab < OpenStruct
       "time" => time,
       "source_modified_time" => source_modified_time.to_i,
       "HEAD" => self.HEAD,
-      "stdlib" => (stdlib.to_s if stdlib),
-      "compiler" => (compiler.to_s if compiler),
+      "stdlib" => (stdlib&.to_s),
+      "compiler" => (compiler&.to_s),
       "aliases" => aliases,
       "runtime_dependencies" => runtime_dependencies,
       "source" => source,
diff --git a/Library/Homebrew/test/Gemfile.lock b/Library/Homebrew/test/Gemfile.lock
index 0d43174e98..b69a5f0a71 100644
--- a/Library/Homebrew/test/Gemfile.lock
+++ b/Library/Homebrew/test/Gemfile.lock
@@ -36,9 +36,9 @@ GEM
     rspec-support (3.7.1)
     rspec-wait (0.0.9)
       rspec (>= 3, < 4)
-    rubocop (0.52.1)
+    rubocop (0.53.0)
       parallel (~> 1.10)
-      parser (>= 2.4.0.2, < 3.0)
+      parser (>= 2.5)
       powerpack (~> 0.1)
       rainbow (>= 2.2.2, < 4.0)
       ruby-progressbar (~> 1.7)
@@ -62,7 +62,7 @@ DEPENDENCIES
   rspec-its
   rspec-retry
   rspec-wait
-  rubocop (= 0.52.1)
+  rubocop (= 0.53.0)
   simplecov
 
 BUNDLED WITH
diff --git a/Library/Homebrew/test/cmd/search_remote_tap_spec.rb b/Library/Homebrew/test/cmd/search_remote_tap_spec.rb
index eb256b9245..49678f3ace 100644
--- a/Library/Homebrew/test/cmd/search_remote_tap_spec.rb
+++ b/Library/Homebrew/test/cmd/search_remote_tap_spec.rb
@@ -16,7 +16,7 @@ describe Homebrew do
       ],
     }
 
-    allow(GitHub).to receive(:open).and_yield(json_response)
+    allow(GitHub).to receive(:open_api).and_yield(json_response)
 
     expect(described_class.search_taps("some-formula"))
       .to match(["homebrew/foo/some-formula"])
diff --git a/Library/Homebrew/test/download_strategies_spec.rb b/Library/Homebrew/test/download_strategies_spec.rb
index 7ad070fc44..f1c64db717 100644
--- a/Library/Homebrew/test/download_strategies_spec.rb
+++ b/Library/Homebrew/test/download_strategies_spec.rb
@@ -116,7 +116,7 @@ describe GitHubPrivateRepositoryReleaseDownloadStrategy do
   describe "#fetch_release_metadata" do
     it "fetches release metadata from GitHub" do
       expected_release_url = "https://api.github.com/repos/owner/repo/releases/tags/tag"
-      expect(GitHub).to receive(:open).with(expected_release_url).and_return({})
+      expect(GitHub).to receive(:open_api).with(expected_release_url).and_return({})
       subject.send(:fetch_release_metadata)
     end
   end
diff --git a/Library/Homebrew/test/support/lib/config.rb b/Library/Homebrew/test/support/lib/config.rb
index e54fc111fa..a59d80c995 100644
--- a/Library/Homebrew/test/support/lib/config.rb
+++ b/Library/Homebrew/test/support/lib/config.rb
@@ -16,9 +16,9 @@ TEST_TMPDIR = ENV.fetch("HOMEBREW_TEST_TMPDIR") do |k|
 end
 
 # Paths pointing into the Homebrew code base that persist across test runs
-HOMEBREW_LIBRARY_PATH  = Pathname.new(File.expand_path("../../../..", __FILE__))
+HOMEBREW_LIBRARY_PATH  = Pathname.new(File.expand_path("../../..", __dir__))
 HOMEBREW_SHIMS_PATH    = HOMEBREW_LIBRARY_PATH.parent+"Homebrew/shims"
-HOMEBREW_LOAD_PATH     = [File.expand_path("..", __FILE__), HOMEBREW_LIBRARY_PATH].join(":")
+HOMEBREW_LOAD_PATH     = [File.expand_path(__dir__), HOMEBREW_LIBRARY_PATH].join(":")
 
 # Paths redirected to a temporary directory and wiped at the end of the test run
 HOMEBREW_PREFIX        = Pathname.new(TEST_TMPDIR).join("prefix")
diff --git a/Library/Homebrew/test/utils/analytics_spec.rb b/Library/Homebrew/test/utils/analytics_spec.rb
index bb6cda0b12..4526194d81 100644
--- a/Library/Homebrew/test/utils/analytics_spec.rb
+++ b/Library/Homebrew/test/utils/analytics_spec.rb
@@ -3,9 +3,9 @@ require "formula_installer"
 
 describe Utils::Analytics do
   describe "::os_prefix_ci" do
-    context "when anonymous_os_prefix_ci is not set" do
+    context "when os_prefix_ci is not set" do
       before(:each) do
-        described_class.clear_anonymous_os_prefix_ci_cache
+        described_class.clear_os_prefix_ci
       end
 
       it "returns OS_VERSION and prefix when HOMEBREW_PREFIX is not /usr/local" do
diff --git a/Library/Homebrew/utils/analytics.rb b/Library/Homebrew/utils/analytics.rb
index adef3e811d..7636789c53 100644
--- a/Library/Homebrew/utils/analytics.rb
+++ b/Library/Homebrew/utils/analytics.rb
@@ -3,13 +3,13 @@ require "erb"
 module Utils
   module Analytics
     class << self
-      def clear_anonymous_os_prefix_ci_cache
-        return unless instance_variable_defined?(:@anonymous_os_prefix_ci)
-        remove_instance_variable(:@anonymous_os_prefix_ci)
+      def clear_os_prefix_ci
+        return unless instance_variable_defined?(:@os_prefix_ci)
+        remove_instance_variable(:@os_prefix_ci)
       end
 
       def os_prefix_ci
-        @anonymous_os_prefix_ci ||= begin
+        @os_prefix_ci ||= begin
           os = OS_VERSION
           prefix = ", non-/usr/local" if HOMEBREW_PREFIX.to_s != "/usr/local"
           ci = ", CI" if ENV["CI"]
diff --git a/Library/Homebrew/utils/bottles.rb b/Library/Homebrew/utils/bottles.rb
index 3a61cf215e..f67ace4c19 100644
--- a/Library/Homebrew/utils/bottles.rb
+++ b/Library/Homebrew/utils/bottles.rb
@@ -5,7 +5,7 @@ module Utils
   class Bottles
     class << self
       def tag
-        @bottle_tag ||= "#{ENV["HOMEBREW_PROCESSOR"]}_#{ENV["HOMEBREW_SYSTEM"]}".downcase.to_sym
+        @tag ||= "#{ENV["HOMEBREW_PROCESSOR"]}_#{ENV["HOMEBREW_SYSTEM"]}".downcase.to_sym
       end
 
       def built_as?(f)
diff --git a/Library/Homebrew/utils/git.rb b/Library/Homebrew/utils/git.rb
index ac17967c53..0ffcab7b1d 100644
--- a/Library/Homebrew/utils/git.rb
+++ b/Library/Homebrew/utils/git.rb
@@ -27,7 +27,7 @@ end
 
 module Utils
   def self.git_available?
-    @git ||= quiet_system HOMEBREW_SHIMS_PATH/"scm/git", "--version"
+    @git_available ||= quiet_system HOMEBREW_SHIMS_PATH/"scm/git", "--version"
   end
 
   def self.git_path
@@ -61,7 +61,7 @@ module Utils
   end
 
   def self.clear_git_available_cache
-    @git = nil
+    @git_available = nil
     @git_path = nil
     @git_version = nil
   end
diff --git a/Library/Homebrew/utils/github.rb b/Library/Homebrew/utils/github.rb
index 0166763234..b6a27b3283 100644
--- a/Library/Homebrew/utils/github.rb
+++ b/Library/Homebrew/utils/github.rb
@@ -94,7 +94,7 @@ module GitHub
   def api_credentials_error_message(response_headers, needed_scopes)
     return if response_headers.empty?
 
-    @api_credentials_error_message_printed ||= begin
+    @api_credentials_error_message ||= begin
       unauthorized = (response_headers["http/1.1"] == "401 Unauthorized")
       scopes = response_headers["x-accepted-oauth-scopes"].to_s.split(", ")
       needed_human_scopes = needed_scopes.join(", ")
@@ -125,7 +125,7 @@ module GitHub
     end
   end
 
-  def open(url, data: nil, scopes: [].freeze)
+  def open_api(url, data: nil, scopes: [].freeze)
     # This is a no-op if the user is opting out of using the GitHub API.
     return block_given? ? yield({}) : {} if ENV["HOMEBREW_NO_GITHUB_API"]
 
@@ -226,7 +226,7 @@ module GitHub
   end
 
   def repository(user, repo)
-    open(url_to("repos", user, repo))
+    open_api(url_to("repos", user, repo))
   end
 
   def search_code(**qualifiers)
@@ -255,7 +255,7 @@ module GitHub
 
   def private_repo?(full_name)
     uri = url_to "repos", full_name
-    open(uri) { |json| json["private"] }
+    open_api(uri) { |json| json["private"] }
   end
 
   def query_string(*main_params, **qualifiers)
@@ -275,6 +275,6 @@ module GitHub
   def search(entity, *queries, **qualifiers)
     uri = url_to "search", entity
     uri.query = query_string(*queries, **qualifiers)
-    open(uri) { |json| json.fetch("items", []) }
+    open_api(uri) { |json| json.fetch("items", []) }
   end
 end