diff --git a/Library/Homebrew/cask/cmd/audit.rb b/Library/Homebrew/cask/cmd/audit.rb
index 6326446fcf..80fadd1fe9 100644
--- a/Library/Homebrew/cask/cmd/audit.rb
+++ b/Library/Homebrew/cask/cmd/audit.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "utils/github/actions"
@@ -13,6 +13,7 @@ module Cask
 
       def self.parser
         super do
+          T.bind(self, Homebrew::CLI::Parser)
           switch "--[no-]download",
                  description: "Audit the downloaded file"
           switch "--[no-]appcast",
@@ -44,7 +45,7 @@ module Cask
         end
         casks = casks.map { |c| CaskLoader.load(c, config: Config.from_args(args)) }
         any_named_args = casks.any?
-        casks = Cask.to_a if casks.empty?
+        casks = Cask.all if casks.empty?
 
         results = self.class.audit_casks(
           *casks,
diff --git a/Library/Homebrew/cask/cmd/fetch.rb b/Library/Homebrew/cask/cmd/fetch.rb
index da0eb66295..784cd06f8e 100644
--- a/Library/Homebrew/cask/cmd/fetch.rb
+++ b/Library/Homebrew/cask/cmd/fetch.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 module Cask
@@ -11,6 +11,7 @@ module Cask
 
       def self.parser
         super do
+          T.bind(self, Homebrew::CLI::Parser)
           switch "--force",
                  description: "Force redownloading even if files already exist in local cache."
         end
diff --git a/Library/Homebrew/cask/cmd/install.rb b/Library/Homebrew/cask/cmd/install.rb
index efd84d9365..11cf1f9a1d 100644
--- a/Library/Homebrew/cask/cmd/install.rb
+++ b/Library/Homebrew/cask/cmd/install.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "cask_dependent"
@@ -27,6 +27,7 @@ module Cask
 
       def self.parser(&block)
         super do
+          T.bind(self, Homebrew::CLI::Parser)
           switch "--force",
                  description: "Force overwriting existing files."
 
diff --git a/Library/Homebrew/cask/cmd/uninstall.rb b/Library/Homebrew/cask/cmd/uninstall.rb
index 1700482a65..67be493145 100644
--- a/Library/Homebrew/cask/cmd/uninstall.rb
+++ b/Library/Homebrew/cask/cmd/uninstall.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 module Cask
@@ -11,6 +11,7 @@ module Cask
 
       def self.parser
         super do
+          T.bind(self, Homebrew::CLI::Parser)
           switch "--force",
                  description: "Uninstall even if the <cask> is not installed, overwrite " \
                               "existing files and ignore errors when removing files."
diff --git a/Library/Homebrew/cask/cmd/upgrade.rb b/Library/Homebrew/cask/cmd/upgrade.rb
index 15dd0d6f08..134563702a 100644
--- a/Library/Homebrew/cask/cmd/upgrade.rb
+++ b/Library/Homebrew/cask/cmd/upgrade.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 require "env_config"
@@ -30,6 +30,7 @@ module Cask
       sig { returns(Homebrew::CLI::Parser) }
       def self.parser
         super do
+          T.bind(self, Homebrew::CLI::Parser)
           switch "--force",
                  description: "Force overwriting existing files."
           switch "--dry-run",
@@ -176,7 +177,9 @@ module Cask
 
         return true if caught_exceptions.empty?
         raise MultipleCaskErrors, caught_exceptions if caught_exceptions.count > 1
-        raise caught_exceptions.first if caught_exceptions.count == 1
+        raise caught_exceptions.fetch(0) if caught_exceptions.count == 1
+
+        false
       end
 
       def self.upgrade_cask(
diff --git a/Library/Homebrew/cask/cmd/zap.rb b/Library/Homebrew/cask/cmd/zap.rb
index b06bfa4223..31460340b2 100644
--- a/Library/Homebrew/cask/cmd/zap.rb
+++ b/Library/Homebrew/cask/cmd/zap.rb
@@ -1,4 +1,4 @@
-# typed: false
+# typed: true
 # frozen_string_literal: true
 
 module Cask
@@ -11,6 +11,7 @@ module Cask
 
       def self.parser
         super do
+          T.bind(self, Homebrew::CLI::Parser)
           switch "--force",
                  description: "Ignore errors when removing files."
         end
diff --git a/Library/Homebrew/test/cask/cmd/audit_spec.rb b/Library/Homebrew/test/cask/cmd/audit_spec.rb
index 1c48cc123f..27859bb32f 100644
--- a/Library/Homebrew/test/cask/cmd/audit_spec.rb
+++ b/Library/Homebrew/test/cask/cmd/audit_spec.rb
@@ -10,7 +10,7 @@ describe Cask::Cmd::Audit, :cask do
 
   describe "selection of Casks to audit" do
     it "audits all Casks if no tokens are given" do
-      allow(Cask::Cask).to receive(:to_a).and_return([cask, cask])
+      allow(Cask::Cask).to receive(:all).and_return([cask, cask])
 
       expect(Cask::Auditor).to receive(:audit).twice.and_return(result)