diff --git a/Library/Homebrew/cask/lib/hbc.rb b/Library/Homebrew/cask/lib/hbc.rb
index efce21391e..9c8c67f518 100644
--- a/Library/Homebrew/cask/lib/hbc.rb
+++ b/Library/Homebrew/cask/lib/hbc.rb
@@ -25,10 +25,3 @@ require "hbc/url"
 require "hbc/utils"
 require "hbc/verify"
 require "hbc/version"
-
-module Hbc
-  def self.init
-    Cache.ensure_cache_exists
-    Caskroom.ensure_caskroom_exists
-  end
-end
diff --git a/Library/Homebrew/cask/lib/hbc/cache.rb b/Library/Homebrew/cask/lib/hbc/cache.rb
index 461ce2c84e..96260b83ff 100644
--- a/Library/Homebrew/cask/lib/hbc/cache.rb
+++ b/Library/Homebrew/cask/lib/hbc/cache.rb
@@ -5,12 +5,5 @@ module Hbc
     def path
       @path ||= HOMEBREW_CACHE.join("Cask")
     end
-
-    def ensure_cache_exists
-      return if path.exist?
-
-      odebug "Creating Cache at #{path}"
-      path.mkpath
-    end
   end
 end
diff --git a/Library/Homebrew/cask/lib/hbc/caskroom.rb b/Library/Homebrew/cask/lib/hbc/caskroom.rb
index 4ed4a2b7a5..cd3e1d52b9 100644
--- a/Library/Homebrew/cask/lib/hbc/caskroom.rb
+++ b/Library/Homebrew/cask/lib/hbc/caskroom.rb
@@ -9,10 +9,12 @@ module Hbc
     def ensure_caskroom_exists
       return if path.exist?
 
-      ohai "Creating Caskroom at #{path}" if $stdout.tty?
       sudo = !path.parent.writable?
 
-      ohai "We'll set permissions properly so we won't need sudo in the future" if $stdout.tty? && sudo
+      if sudo && !ENV.key?("SUDO_ASKPASS") && $stdout.tty?
+        ohai "Creating Caskroom at #{path}"
+        ohai "We'll set permissions properly so we won't need sudo in the future."
+      end
 
       SystemCommand.run("/bin/mkdir", args: ["-p", path], sudo: sudo)
       SystemCommand.run("/bin/chmod", args: ["g+rwx", path], sudo: sudo)
@@ -21,6 +23,8 @@ module Hbc
     end
 
     def casks
+      return [] unless path.exist?
+
       Pathname.glob(path.join("*")).sort.select(&:directory?).map do |path|
         token = path.basename.to_s
 
diff --git a/Library/Homebrew/cask/lib/hbc/cli.rb b/Library/Homebrew/cask/lib/hbc/cli.rb
index 57cec17469..b75d5e63de 100644
--- a/Library/Homebrew/cask/lib/hbc/cli.rb
+++ b/Library/Homebrew/cask/lib/hbc/cli.rb
@@ -88,10 +88,6 @@ module Hbc
       @lookup.fetch(command_name, command_name)
     end
 
-    def self.should_init?(command)
-      command.is_a?(Class) && !command.abstract? && command.needs_init?
-    end
-
     def self.run_command(command, *args)
       if command.respond_to?(:run)
         # usual case: built-in command verb
@@ -164,7 +160,6 @@ module Hbc
       MacOS.full_version = ENV["MACOS_VERSION"] unless ENV["MACOS_VERSION"].nil?
 
       Tap.default_cask_tap.install unless Tap.default_cask_tap.installed?
-      Hbc.init if self.class.should_init?(command)
       self.class.run_command(command, *args)
     rescue CaskError, ArgumentError, OptionParser::InvalidOption => e
       msg = e.message
diff --git a/Library/Homebrew/cask/lib/hbc/cli/abstract_command.rb b/Library/Homebrew/cask/lib/hbc/cli/abstract_command.rb
index 2cfe3c467d..e6313b5fc5 100644
--- a/Library/Homebrew/cask/lib/hbc/cli/abstract_command.rb
+++ b/Library/Homebrew/cask/lib/hbc/cli/abstract_command.rb
@@ -27,10 +27,6 @@ module Hbc
         nil
       end
 
-      def self.needs_init?
-        false
-      end
-
       def self.run(*args)
         new(*args).run
       end
diff --git a/Library/Homebrew/cask/lib/hbc/cli/audit.rb b/Library/Homebrew/cask/lib/hbc/cli/audit.rb
index 2b89a8d2c3..c1bb5bcd8c 100644
--- a/Library/Homebrew/cask/lib/hbc/cli/audit.rb
+++ b/Library/Homebrew/cask/lib/hbc/cli/audit.rb
@@ -20,10 +20,6 @@ module Hbc
         odebug "Auditing Cask #{cask}"
         Auditor.audit(cask, audit_download: download?, check_token_conflicts: token_conflicts?)
       end
-
-      def self.needs_init?
-        true
-      end
     end
   end
 end
diff --git a/Library/Homebrew/cask/lib/hbc/cli/cleanup.rb b/Library/Homebrew/cask/lib/hbc/cli/cleanup.rb
index 15a85d123b..1553d8e85d 100644
--- a/Library/Homebrew/cask/lib/hbc/cli/cleanup.rb
+++ b/Library/Homebrew/cask/lib/hbc/cli/cleanup.rb
@@ -8,10 +8,6 @@ module Hbc
         "cleans up cached downloads and tracker symlinks"
       end
 
-      def self.needs_init?
-        true
-      end
-
       attr_reader :cache_location
 
       def initialize(*args, cache_location: Cache.path)
@@ -24,7 +20,7 @@ module Hbc
       end
 
       def cache_files
-        return [] unless cache_location.exist?
+        return [] unless cache_location.directory?
         cache_location.children
                       .map(&method(:Pathname))
                       .reject(&method(:outdated?))
diff --git a/Library/Homebrew/cask/lib/hbc/cli/doctor.rb b/Library/Homebrew/cask/lib/hbc/cli/doctor.rb
index e60103d290..63edf2d55c 100644
--- a/Library/Homebrew/cask/lib/hbc/cli/doctor.rb
+++ b/Library/Homebrew/cask/lib/hbc/cli/doctor.rb
@@ -62,9 +62,7 @@ module Hbc
 
         path = Pathname.new(user_tilde(Caskroom.path.to_s))
 
-        if !path.exist?
-          add_error "The staging path #{path} does not exist."
-        elsif !path.writable?
+        if path.exist? && !path.writable?
           add_error "The staging path #{path} is not writable by the current user."
         end
 
diff --git a/Library/Homebrew/cask/lib/hbc/cli/fetch.rb b/Library/Homebrew/cask/lib/hbc/cli/fetch.rb
index 12c794f5f6..f76927297c 100644
--- a/Library/Homebrew/cask/lib/hbc/cli/fetch.rb
+++ b/Library/Homebrew/cask/lib/hbc/cli/fetch.rb
@@ -17,10 +17,6 @@ module Hbc
         end
       end
 
-      def self.needs_init?
-        true
-      end
-
       def self.help
         "downloads remote application files to local cache"
       end
diff --git a/Library/Homebrew/cask/lib/hbc/cli/install.rb b/Library/Homebrew/cask/lib/hbc/cli/install.rb
index d8f148b1ba..31d90f60ef 100644
--- a/Library/Homebrew/cask/lib/hbc/cli/install.rb
+++ b/Library/Homebrew/cask/lib/hbc/cli/install.rb
@@ -27,10 +27,6 @@ module Hbc
       def self.help
         "installs the given Cask"
       end
-
-      def self.needs_init?
-        true
-      end
     end
   end
 end
diff --git a/Library/Homebrew/cask/lib/hbc/cli/internal_appcast_checkpoint.rb b/Library/Homebrew/cask/lib/hbc/cli/internal_appcast_checkpoint.rb
index a538ffd8c3..a88d1fc170 100644
--- a/Library/Homebrew/cask/lib/hbc/cli/internal_appcast_checkpoint.rb
+++ b/Library/Homebrew/cask/lib/hbc/cli/internal_appcast_checkpoint.rb
@@ -49,10 +49,6 @@ module Hbc
       def self.help
         "prints or calculates a given Cask's or URL's appcast checkpoint"
       end
-
-      def self.needs_init?
-        true
-      end
     end
   end
 end
diff --git a/Library/Homebrew/cask/lib/hbc/cli/internal_audit_modified_casks.rb b/Library/Homebrew/cask/lib/hbc/cli/internal_audit_modified_casks.rb
index f06e2acc58..eadd8e2839 100644
--- a/Library/Homebrew/cask/lib/hbc/cli/internal_audit_modified_casks.rb
+++ b/Library/Homebrew/cask/lib/hbc/cli/internal_audit_modified_casks.rb
@@ -5,10 +5,6 @@ module Hbc
 
       option "--cleanup", :cleanup, false
 
-      def self.needs_init?
-        true
-      end
-
       attr_accessor :commit_range
       private :commit_range=
 
diff --git a/Library/Homebrew/cask/lib/hbc/cli/list.rb b/Library/Homebrew/cask/lib/hbc/cli/list.rb
index 788b0eede5..916860e7e2 100644
--- a/Library/Homebrew/cask/lib/hbc/cli/list.rb
+++ b/Library/Homebrew/cask/lib/hbc/cli/list.rb
@@ -57,10 +57,6 @@ module Hbc
       def self.help
         "with no args, lists installed Casks; given installed Casks, lists staged files"
       end
-
-      def self.needs_init?
-        true
-      end
     end
   end
 end
diff --git a/Library/Homebrew/cask/lib/hbc/cli/upgrade.rb b/Library/Homebrew/cask/lib/hbc/cli/upgrade.rb
index 3969546712..e0589eb0d0 100644
--- a/Library/Homebrew/cask/lib/hbc/cli/upgrade.rb
+++ b/Library/Homebrew/cask/lib/hbc/cli/upgrade.rb
@@ -16,7 +16,10 @@ module Hbc
           Caskroom.casks.select do |cask|
             cask.outdated?(greedy?)
           end
-        }).select { |cask| cask.outdated?(true) }
+        }).select do |cask|
+          raise CaskNotInstalledError, cask unless cask.installed? || force?
+          cask.outdated?(true)
+        end
 
         if outdated_casks.empty?
           oh1 "No Casks to upgrade"
@@ -28,8 +31,6 @@ module Hbc
 
         outdated_casks.each do |old_cask|
           odebug "Started upgrade process for Cask #{old_cask}"
-          raise CaskNotInstalledError, old_cask unless old_cask.installed? || force?
-
           raise CaskUnavailableError.new(old_cask, "The Caskfile is missing!") if old_cask.installed_caskfile.nil?
 
           old_cask = CaskLoader.load(old_cask.installed_caskfile)
@@ -82,10 +83,6 @@ module Hbc
       def self.help
         "upgrades all outdated casks"
       end
-
-      def self.needs_init?
-        true
-      end
     end
   end
 end
diff --git a/Library/Homebrew/cask/lib/hbc/download_strategy.rb b/Library/Homebrew/cask/lib/hbc/download_strategy.rb
index edcab1d320..44ef287b70 100644
--- a/Library/Homebrew/cask/lib/hbc/download_strategy.rb
+++ b/Library/Homebrew/cask/lib/hbc/download_strategy.rb
@@ -95,6 +95,8 @@ module Hbc
     end
 
     def fetch
+      tarball_path.dirname.mkpath
+
       ohai "Downloading #{@url}"
       if tarball_path.exist?
         puts "Already downloaded: #{tarball_path}"
@@ -193,6 +195,8 @@ module Hbc
 
     # super does not provide checks for already-existing downloads
     def fetch
+      cached_location.dirname.mkpath
+
       if cached_location.directory?
         puts "Already downloaded: #{cached_location}"
       else
diff --git a/Library/Homebrew/cask/lib/hbc/installer.rb b/Library/Homebrew/cask/lib/hbc/installer.rb
index 90e4c286d4..eb55c9c941 100644
--- a/Library/Homebrew/cask/lib/hbc/installer.rb
+++ b/Library/Homebrew/cask/lib/hbc/installer.rb
@@ -55,6 +55,8 @@ module Hbc
     def stage
       odebug "Hbc::Installer#stage"
 
+      Caskroom.ensure_caskroom_exists
+
       extract_primary_container
       save_caskfile
     rescue StandardError => e
diff --git a/Library/Homebrew/test/support/helper/spec/shared_context/homebrew_cask.rb b/Library/Homebrew/test/support/helper/spec/shared_context/homebrew_cask.rb
index 62e682966b..e021eb3f7e 100644
--- a/Library/Homebrew/test/support/helper/spec/shared_context/homebrew_cask.rb
+++ b/Library/Homebrew/test/support/helper/spec/shared_context/homebrew_cask.rb
@@ -23,7 +23,7 @@ RSpec.shared_context "Homebrew-Cask" do
     begin
       HOMEBREW_CASK_DIRS.values.each(&:mkpath)
 
-      [Hbc::Config.global.binarydir, Hbc::Caskroom.path, Hbc::Cache.path].each(&:mkpath)
+      [Hbc::Config.global.binarydir].each(&:mkpath)
 
       Tap.default_cask_tap.tap do |tap|
         FileUtils.mkdir_p tap.path.dirname