diff --git a/Library/Homebrew/cmd/install.rb b/Library/Homebrew/cmd/install.rb
index c4125ba426..517414f9fe 100644
--- a/Library/Homebrew/cmd/install.rb
+++ b/Library/Homebrew/cmd/install.rb
@@ -43,6 +43,10 @@ module Homebrew
                description: "Print the verification and post-install steps."
         switch "-n", "--dry-run",
                description: "Show what would be installed, but do not actually install anything."
+        switch "--ask",
+               env:         :ask,
+               description: "Ask for confirmation before downloading and installing formulae. " \
+                            "Print bottles and dependencies download size and install size."
         [
           [:switch, "--formula", "--formulae", {
             description: "Treat all named arguments as formulae.",
@@ -123,11 +127,6 @@ module Homebrew
           [:switch, "--overwrite", {
             description: "Delete files that already exist in the prefix while linking.",
           }],
-          [:switch, "--ask", {
-            description: "Ask for confirmation before downloading and installing formulae. " \
-                         "Print bottles and dependencies download size and install size.",
-            env:         :ask,
-          }],
         ].each do |args|
           options = args.pop
           send(*args, **options)
@@ -218,6 +217,7 @@ module Homebrew
         end
 
         if casks.any?
+          Install.ask_casks casks if args.ask?
           if args.dry_run?
             if (casks_to_install = casks.reject(&:installed?).presence)
               ohai "Would install #{::Utils.pluralize("cask", casks_to_install.count, include_count: true)}:"
@@ -310,7 +310,7 @@ module Homebrew
         Install.perform_preinstall_checks_once
         Install.check_cc_argv(args.cc)
 
-        Install.ask(formulae, args: args) if args.ask?
+        Install.ask_formulae(installed_formulae, args: args) if args.ask?
 
         Install.install_formulae(
           installed_formulae,
diff --git a/Library/Homebrew/cmd/reinstall.rb b/Library/Homebrew/cmd/reinstall.rb
index 3c767f0619..2c1208e54a 100644
--- a/Library/Homebrew/cmd/reinstall.rb
+++ b/Library/Homebrew/cmd/reinstall.rb
@@ -39,6 +39,10 @@ module Homebrew
                             "non-migrated versions."
         switch "-v", "--verbose",
                description: "Print the verification and post-install steps."
+        switch "--ask",
+               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." }],
           [:switch, "-s", "--build-from-source", {
@@ -63,11 +67,6 @@ module Homebrew
           [:switch, "-g", "--git", {
             description: "Create a Git repository, useful for creating patches to the software.",
           }],
-          [:switch, "--ask", {
-            description: "Ask for confirmation before downloading and upgrading formulae. " \
-                         "Print bottles and dependencies download size, install and net install size.",
-            env:         :ask,
-          }],
         ].each do |args|
           options = args.pop
           send(*args, **options)
@@ -132,7 +131,7 @@ module Homebrew
           Install.perform_preinstall_checks_once
 
           # If asking the user is enabled, show dependency and size information.
-          Install.ask(formulae, args: args) if args.ask?
+          Install.ask_formulae(formulae, args: args) if args.ask?
 
           formulae.each do |formula|
             if formula.pinned?
@@ -173,6 +172,7 @@ module Homebrew
         end
 
         if casks.any?
+          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 b48ace323d..7e053982e0 100644
--- a/Library/Homebrew/cmd/upgrade.rb
+++ b/Library/Homebrew/cmd/upgrade.rb
@@ -39,6 +39,10 @@ module Homebrew
                description: "Print the verification and post-install steps."
         switch "-n", "--dry-run",
                description: "Show what would be upgraded, but do not actually upgrade anything."
+        switch "--ask",
+               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 " \
@@ -71,11 +75,6 @@ module Homebrew
           [:switch, "--overwrite", {
             description: "Delete files that already exist in the prefix while linking.",
           }],
-          [:switch, "--ask", {
-            description: "Ask for confirmation before downloading and upgrading formulae. " \
-                         "Print bottles and dependencies download size, install and net install size.",
-            env:         :ask,
-          }],
         ].each do |args|
           options = args.pop
           send(*args, **options)
@@ -222,7 +221,7 @@ module Homebrew
         Install.perform_preinstall_checks_once
 
         # Main block: if asking the user is enabled, show dependency and size information.
-        Install.ask(formulae_to_install, args: args) if args.ask?
+        Install.ask_formulae(formulae_to_install, args: args) if args.ask?
 
         Upgrade.upgrade_formulae(
           formulae_to_install,
@@ -262,6 +261,8 @@ module Homebrew
       def upgrade_outdated_casks(casks)
         return false if args.formula?
 
+        Install.ask_casks casks
+
         Cask::Upgrade.upgrade_casks(
           *casks,
           force:               args.force?,
diff --git a/Library/Homebrew/install.rb b/Library/Homebrew/install.rb
index f001f41578..8fba7fabf7 100644
--- a/Library/Homebrew/install.rb
+++ b/Library/Homebrew/install.rb
@@ -331,7 +331,9 @@ module Homebrew
       end
 
       # If asking the user is enabled, show dependency and size information.
-      def ask(formulae, args:)
+      def ask_formulae(formulae, args:)
+        return if formulae.empty?
+
         ohai "Looking for bottles..."
 
         sized_formulae = compute_sized_formulae(formulae, args: args)
@@ -346,6 +348,15 @@ module Homebrew
         ask_input
       end
 
+      def ask_casks(casks)
+        return if casks.empty?
+
+        puts "#{::Utils.pluralize("Cask", casks.count, plural: "s")} \
+(#{casks.count}): #{casks.join(", ")}\n\n"
+
+        ask_input
+      end
+
       private
 
       def perform_preinstall_checks(all_fatal: false)