diff --git a/Library/Homebrew/cask/installer.rb b/Library/Homebrew/cask/installer.rb
index cb91c6513f..967971247c 100644
--- a/Library/Homebrew/cask/installer.rb
+++ b/Library/Homebrew/cask/installer.rb
@@ -46,6 +46,7 @@ module Cask
       @verify_download_integrity = verify_download_integrity
       @quiet = quiet
       @download_queue = download_queue
+      @ran_prelude = T.let(false, T::Boolean)
     end
 
     sig { returns(T::Boolean) }
@@ -140,8 +141,7 @@ module Cask
       old_config = @cask.config
       predecessor = @cask if reinstall? && @cask.installed?
 
-      check_deprecate_disable
-      check_conflicts
+      prelude
 
       print caveats
       fetch
@@ -791,6 +791,16 @@ on_request: true)
       )
     end
 
+    sig { void }
+    def prelude
+      return if @ran_prelude
+
+      check_deprecate_disable
+      check_conflicts
+
+      @ran_prelude = true
+    end
+
     sig { void }
     def enqueue_downloads
       download_queue = @download_queue
diff --git a/Library/Homebrew/cask/reinstall.rb b/Library/Homebrew/cask/reinstall.rb
index 3a6ea68e46..970a5daf6b 100644
--- a/Library/Homebrew/cask/reinstall.rb
+++ b/Library/Homebrew/cask/reinstall.rb
@@ -30,6 +30,8 @@ module Cask
       end
 
       if download_queue
+        cask_installers.each(&:prelude)
+
         oh1 "Fetching downloads for: #{casks.map { |cask| Formatter.identifier(cask.full_name) }.to_sentence}",
             truncate: false
         cask_installers.each(&:enqueue_downloads)
diff --git a/Library/Homebrew/cask/upgrade.rb b/Library/Homebrew/cask/upgrade.rb
index 91ee0090f0..7b4d1fbeab 100644
--- a/Library/Homebrew/cask/upgrade.rb
+++ b/Library/Homebrew/cask/upgrade.rb
@@ -115,19 +115,22 @@ module Cask
         download_queue = Homebrew::DownloadQueue.new(pour: true)
 
         fetchable_casks = upgradable_casks.map(&:last)
-        fetchable_casks_sentence = fetchable_casks.map { |cask| Formatter.identifier(cask.full_name) }.to_sentence
-        oh1 "Fetching downloads for: #{fetchable_casks_sentence}", truncate: false
-
-        fetchable_casks.each do |cask|
+        fetchable_cask_installers = fetchable_casks.map do |cask|
           # This is significantly easier given the weird difference in Sorbet signatures here.
           # rubocop:disable Style/DoubleNegation
           Installer.new(cask, binaries: !!binaries, verbose: !!verbose, force: !!force,
                                                skip_cask_deps: !!skip_cask_deps, require_sha: !!require_sha,
                                                upgrade: true, quarantine:, download_queue:)
-                   .enqueue_downloads
           # rubocop:enable Style/DoubleNegation
         end
 
+        fetchable_cask_installers.each(&:prelude)
+
+        fetchable_casks_sentence = fetchable_casks.map { |cask| Formatter.identifier(cask.full_name) }.to_sentence
+        oh1 "Fetching downloads for: #{fetchable_casks_sentence}", truncate: false
+
+        fetchable_cask_installers.each(&:enqueue_downloads)
+
         download_queue.fetch
       end
 
diff --git a/Library/Homebrew/cmd/install.rb b/Library/Homebrew/cmd/install.rb
index 55e3ca82d1..30ad5392db 100644
--- a/Library/Homebrew/cmd/install.rb
+++ b/Library/Homebrew/cmd/install.rb
@@ -248,17 +248,21 @@ module Homebrew
           fetch_casks = Homebrew::EnvConfig.no_install_upgrade? ? new_casks : casks
 
           if download_queue
-            fetch_casks_sentence = fetch_casks.map { |cask| Formatter.identifier(cask.full_name) }.to_sentence
-            oh1 "Fetching downloads for: #{fetch_casks_sentence}", truncate: false
-
-            fetch_casks.each do |cask|
+            fetch_cask_installers = fetch_casks.map do |cask|
               Cask::Installer.new(cask, binaries: args.binaries?, verbose: args.verbose?,
                                                    force: args.force?, skip_cask_deps: args.skip_cask_deps?,
                                                    require_sha: args.require_sha?, reinstall: true,
                                                    quarantine: args.quarantine?, zap: args.zap?, download_queue:)
-                             .enqueue_downloads
             end
 
+            # Run prelude checks for all casks before enqueueing downloads
+            fetch_cask_installers.each(&:prelude)
+
+            fetch_casks_sentence = fetch_casks.map { |cask| Formatter.identifier(cask.full_name) }.to_sentence
+            oh1 "Fetching downloads for: #{fetch_casks_sentence}", truncate: false
+
+            fetch_cask_installers.each(&:enqueue_downloads)
+
             download_queue.fetch
           end