diff --git a/Library/Homebrew/cmd/reinstall.rb b/Library/Homebrew/cmd/reinstall.rb
index 3774c72390..2c1208e54a 100644
--- a/Library/Homebrew/cmd/reinstall.rb
+++ b/Library/Homebrew/cmd/reinstall.rb
@@ -172,9 +172,7 @@ module Homebrew
         end
 
         if casks.any?
-          if args.ask?
-            Install.ask_casks casks
-          end
+          Install.ask_casks casks if args.ask?
           Cask::Reinstall.reinstall_casks(
             *casks,
             binaries:       args.binaries?,
diff --git a/Library/Homebrew/cmd/upgrade.rb b/Library/Homebrew/cmd/upgrade.rb
index a6b5172489..7e053982e0 100644
--- a/Library/Homebrew/cmd/upgrade.rb
+++ b/Library/Homebrew/cmd/upgrade.rb
@@ -43,7 +43,7 @@ module Homebrew
                description: "Ask for confirmation before downloading and upgrading formulae. " \
                             "Print bottles and dependencies download size, install and net install size.",
                env:         :ask
-          [
+        [
           [:switch, "--formula", "--formulae", {
             description: "Treat all named arguments as formulae. If no named arguments " \
                          "are specified, upgrade only outdated formulae.",
@@ -260,6 +260,7 @@ module Homebrew
       sig { params(casks: T::Array[Cask::Cask]).returns(T::Boolean) }
       def upgrade_outdated_casks(casks)
         return false if args.formula?
+
         Install.ask_casks casks
 
         Cask::Upgrade.upgrade_casks(
diff --git a/Library/Homebrew/install.rb b/Library/Homebrew/install.rb
index c93a0f7610..8fba7fabf7 100644
--- a/Library/Homebrew/install.rb
+++ b/Library/Homebrew/install.rb
@@ -332,7 +332,7 @@ module Homebrew
 
       # If asking the user is enabled, show dependency and size information.
       def ask_formulae(formulae, args:)
-        return if formulae.empty? && casks.empty?
+        return if formulae.empty?
 
         ohai "Looking for bottles..."