diff --git a/Library/Homebrew/cask/cmd/upgrade.rb b/Library/Homebrew/cask/cmd/upgrade.rb
index ae68121826..89c73dd05f 100644
--- a/Library/Homebrew/cask/cmd/upgrade.rb
+++ b/Library/Homebrew/cask/cmd/upgrade.rb
@@ -69,7 +69,7 @@ module Cask
           binaries:       T.nilable(T::Boolean),
           quarantine:     T.nilable(T::Boolean),
           require_sha:    T.nilable(T::Boolean),
-        ).void
+        ).returns(T::Boolean)
       end
       def self.upgrade_casks(
         *casks,
@@ -98,7 +98,7 @@ module Cask
           end
         end
 
-        return if outdated_casks.empty?
+        return false if outdated_casks.empty?
 
         if casks.empty? && !greedy
           ohai "Casks with `auto_updates` or `version :latest` will not be upgraded; pass `--greedy` to upgrade them."
@@ -114,7 +114,7 @@ module Cask
         puts upgradable_casks
           .map { |(old_cask, new_cask)| "#{new_cask.full_name} #{old_cask.version} -> #{new_cask.version}" }
           .join("\n")
-        return if dry_run
+        return true if dry_run
 
         upgradable_casks.each do |(old_cask, new_cask)|
           upgrade_cask(
@@ -127,7 +127,7 @@ module Cask
           next
         end
 
-        return if caught_exceptions.empty?
+        return true if caught_exceptions.empty?
         raise MultipleCaskErrors, caught_exceptions if caught_exceptions.count > 1
         raise caught_exceptions.first if caught_exceptions.count == 1
       end
diff --git a/Library/Homebrew/cmd/upgrade.rb b/Library/Homebrew/cmd/upgrade.rb
index 04839b7123..f134f773e8 100644
--- a/Library/Homebrew/cmd/upgrade.rb
+++ b/Library/Homebrew/cmd/upgrade.rb
@@ -100,16 +100,20 @@ module Homebrew
     # If one or more formulae are specified, but no casks were
     # specified, we want to make note of that so we don't
     # try to upgrade all outdated casks.
-    upgrade_formulae = formulae.present? && casks.blank?
-    upgrade_casks = casks.present? && formulae.blank?
+    only_upgrade_formulae = formulae.present? && casks.blank?
+    only_upgrade_casks = casks.present? && formulae.blank?
 
-    upgrade_outdated_formulae(formulae, args: args) unless upgrade_casks
-    upgrade_outdated_casks(casks, args: args) unless upgrade_formulae
+    display_messages = !only_upgrade_casks && upgrade_outdated_formulae(formulae, args: args)
+    force_caveats = !only_upgrade_formulae && upgrade_outdated_casks(casks, args: args)
+
+    return unless display_messages
+
+    Homebrew.messages.display_messages(force_caveats: force_caveats, display_times: args.display_times?)
   end
 
-  sig { params(formulae: T::Array[Formula], args: CLI::Args).void }
+  sig { params(formulae: T::Array[Formula], args: CLI::Args).returns(T::Boolean) }
   def upgrade_outdated_formulae(formulae, args:)
-    return if args.cask?
+    return false if args.cask?
 
     FormulaInstaller.prevent_build_flags(args)
 
@@ -135,7 +139,7 @@ module Homebrew
       end
     end
 
-    return if outdated.blank?
+    return false if outdated.blank?
 
     pinned = outdated.select(&:pinned?)
     outdated -= pinned
@@ -172,12 +176,12 @@ module Homebrew
 
     Upgrade.check_installed_dependents(formulae_to_install, args: args)
 
-    Homebrew.messages.display_messages(display_times: args.display_times?)
+    true
   end
 
-  sig { params(casks: T::Array[Cask::Cask], args: CLI::Args).void }
+  sig { params(casks: T::Array[Cask::Cask], args: CLI::Args).returns(T::Boolean) }
   def upgrade_outdated_casks(casks, args:)
-    return if args.formula?
+    return false if args.formula?
 
     Cask::Cmd::Upgrade.upgrade_casks(
       *casks,
diff --git a/Library/Homebrew/messages.rb b/Library/Homebrew/messages.rb
index e212896790..0e6b3164f2 100644
--- a/Library/Homebrew/messages.rb
+++ b/Library/Homebrew/messages.rb
@@ -24,13 +24,14 @@ class Messages
     @install_times.push(formula: f.name, time: elapsed_time)
   end
 
-  def display_messages(display_times: false)
-    display_caveats
+  def display_messages(force_caveats: false, display_times: false)
+    display_caveats(force: force_caveats)
     display_install_times if display_times
   end
 
-  def display_caveats
-    return if @formula_count <= 1
+  def display_caveats(force: false)
+    return if @formula_count.zero?
+    return if @formula_count == 1 && !force
     return if @caveats.empty?
 
     oh1 "Caveats"