diff --git a/Library/Homebrew/cask/installer.rb b/Library/Homebrew/cask/installer.rb
index 123796b4564c83..517070f5ba9192 100644
--- a/Library/Homebrew/cask/installer.rb
+++ b/Library/Homebrew/cask/installer.rb
@@ -136,10 +136,9 @@ def check_deprecate_disable
 
       case deprecate_disable_type
       when :deprecated
-        puts "::warning::#{message_full}" if ENV["GITHUB_ACTIONS"]
         opoo message_full
       when :disabled
-        puts "::error::#{message_full}" if ENV["GITHUB_ACTIONS"]
+        GitHub::Actions.puts_annotation_if_env_set(:error, message)
         raise CaskCannotBeInstalledError.new(@cask, message)
       end
     end
diff --git a/Library/Homebrew/dev-cmd/audit.rb b/Library/Homebrew/dev-cmd/audit.rb
index 63e5fdee88d86f..7451f2124f5470 100644
--- a/Library/Homebrew/dev-cmd/audit.rb
+++ b/Library/Homebrew/dev-cmd/audit.rb
@@ -308,7 +308,7 @@ def run
           ofail "#{errors_summary}."
         end
 
-        return unless ENV["GITHUB_ACTIONS"]
+        return unless GitHub::Actions.env_set?
 
         annotations = formula_problems.merge(cask_problems).flat_map do |(_, path), problems|
           problems.map do |problem|
diff --git a/Library/Homebrew/dev-cmd/pr-pull.rb b/Library/Homebrew/dev-cmd/pr-pull.rb
index bd8bc73a5c3bf7..a44279eced5792 100644
--- a/Library/Homebrew/dev-cmd/pr-pull.rb
+++ b/Library/Homebrew/dev-cmd/pr-pull.rb
@@ -170,7 +170,7 @@ def run
               safe_system HOMEBREW_BREW_FILE, *upload_args
             end
           ensure
-            if args.retain_bottle_dir? && ENV["GITHUB_ACTIONS"]
+            if args.retain_bottle_dir? && GitHub::Actions.env_set?
               ohai "Bottle files retained at:", dir
               File.open(ENV.fetch("GITHUB_OUTPUT"), "a") do |f|
                 f.puts "bottle_path=#{dir}"
diff --git a/Library/Homebrew/diagnostic.rb b/Library/Homebrew/diagnostic.rb
index be12eb049c0a62..54398793e71044 100644
--- a/Library/Homebrew/diagnostic.rb
+++ b/Library/Homebrew/diagnostic.rb
@@ -925,7 +925,7 @@ def check_cask_install_location
 
       def check_cask_staging_location
         # Skip this check when running CI since the staging path is not writable for security reasons
-        return if ENV["GITHUB_ACTIONS"]
+        return if GitHub::Actions.env_set?
 
         path = Cask::Caskroom.path
 
diff --git a/Library/Homebrew/extend/kernel.rb b/Library/Homebrew/extend/kernel.rb
index 8696c5cc6baa83..40e489cf8f274e 100644
--- a/Library/Homebrew/extend/kernel.rb
+++ b/Library/Homebrew/extend/kernel.rb
@@ -64,6 +64,7 @@ def oh1(title, truncate: :auto)
   def opoo(message)
     Tty.with($stderr) do |stderr|
       stderr.puts Formatter.warning(message, label: "Warning")
+      GitHub::Actions.puts_annotation_if_env_set(:warning, message)
     end
   end
 
@@ -73,6 +74,7 @@ def opoo(message)
   def onoe(message)
     Tty.with($stderr) do |stderr|
       stderr.puts Formatter.error(message, label: "Error")
+      GitHub::Actions.puts_annotation_if_env_set(:error, message)
     end
   end
 
@@ -146,11 +148,14 @@ def odeprecated(method, replacement = nil,
       next unless (match = line.match(HOMEBREW_TAP_PATH_REGEX))
 
       tap = Tap.fetch(match[:user], match[:repo])
-      tap_message = +"\nPlease report this issue to the #{tap} tap (not Homebrew/brew or Homebrew/homebrew-core)"
+      tap_message = +"\nPlease report this issue to the #{tap.full_name} tap"
+      tap_message += " (not Homebrew/brew or Homebrew/homebrew-core)" unless tap.official?
       tap_message += ", or even better, submit a PR to fix it" if replacement
       tap_message << ":\n  #{line.sub(/^(.*:\d+):.*$/, '\1')}\n\n"
       break
     end
+    file, line, = backtrace.first.split(":")
+    line = line.to_i if line.present?
 
     message = +"Calling #{method} is #{verb}! #{replacement_message}"
     message << tap_message if tap_message
@@ -158,12 +163,13 @@ def odeprecated(method, replacement = nil,
 
     disable = true if disable_for_developers && Homebrew::EnvConfig.developer?
     if disable || Homebrew.raise_deprecation_exceptions?
-      puts "::error::#{message}" if ENV["GITHUB_ACTIONS"]
+      puts GitHub::Actions::Annotation.new(:error, message, file:, line:) if GitHub::Actions.env_set?
+      GitHub::Actions.puts_annotation_if_env_set(:error, message, file:, line:)
       exception = MethodDeprecatedError.new(message)
       exception.set_backtrace(backtrace)
       raise exception
     elsif !Homebrew.auditing?
-      puts "::warning::#{message}" if ENV["GITHUB_ACTIONS"]
+      GitHub::Actions.puts_annotation_if_env_set(:warning, message, file:, line:)
       opoo message
     end
   end
diff --git a/Library/Homebrew/extend/os/mac/diagnostic.rb b/Library/Homebrew/extend/os/mac/diagnostic.rb
index 6733fc0b34b229..923fd1dae5dae2 100644
--- a/Library/Homebrew/extend/os/mac/diagnostic.rb
+++ b/Library/Homebrew/extend/os/mac/diagnostic.rb
@@ -134,7 +134,7 @@ def check_xcode_up_to_date
         # `brew test-bot` runs `brew doctor` in the CI for the Homebrew/brew
         # repository. This only needs to support whatever CI providers
         # Homebrew/brew is currently using.
-        return if ENV["GITHUB_ACTIONS"]
+        return if GitHub::Actions.env_set?
 
         # With fake El Capitan for Portable Ruby, we are intentionally not using Xcode 8.
         # This is because we are not using the CLT and Xcode 8 has the 10.12 SDK.
@@ -165,7 +165,7 @@ def check_clt_up_to_date
         # `brew test-bot` runs `brew doctor` in the CI for the Homebrew/brew
         # repository. This only needs to support whatever CI providers
         # Homebrew/brew is currently using.
-        return if ENV["GITHUB_ACTIONS"]
+        return if GitHub::Actions.env_set?
 
         <<~EOS
           A newer Command Line Tools release is available.
diff --git a/Library/Homebrew/formula_installer.rb b/Library/Homebrew/formula_installer.rb
index 1475a595ff5544..fe9c047dde8365 100644
--- a/Library/Homebrew/formula_installer.rb
+++ b/Library/Homebrew/formula_installer.rb
@@ -205,10 +205,9 @@ def prelude
 
       case deprecate_disable_type
       when :deprecated
-        puts "::warning::#{message}" if ENV["GITHUB_ACTIONS"]
         opoo message
       when :disabled
-        puts "::error::#{message}" if ENV["GITHUB_ACTIONS"]
+        GitHub::Actions.puts_annotation_if_env_set(:error, message)
         raise CannotInstallFormulaError, message
       end
     end
@@ -504,7 +503,8 @@ def check_conflicts
 
       raise if Homebrew::EnvConfig.developer?
 
-      $stderr.puts "Please report this issue to the #{formula.tap} tap (not Homebrew/brew or Homebrew/homebrew-core)!"
+      $stderr.puts "Please report this issue to the #{formula.tap&.full_name} tap".squeeze(" ")
+      $stderr.puts " (not Homebrew/brew or Homebrew/homebrew-core)!" unless formula.core_formula?
       false
     else
       f.linked_keg.exist? && f.opt_prefix.exist?
diff --git a/Library/Homebrew/style.rb b/Library/Homebrew/style.rb
index 066438b32e523a..52c14b638f9e38 100644
--- a/Library/Homebrew/style.rb
+++ b/Library/Homebrew/style.rb
@@ -15,7 +15,7 @@ module Style
     def self.check_style_and_print(files, **options)
       success = check_style_impl(files, :print, **options)
 
-      if ENV["GITHUB_ACTIONS"] && !success
+      if GitHub::Actions.env_set? && !success
         check_style_json(files, **options).each do |path, offenses|
           offenses.each do |o|
             line = o.location.line
diff --git a/Library/Homebrew/test/extend/kernel_spec.rb b/Library/Homebrew/test/extend/kernel_spec.rb
index 200756b4cf9801..238f4573e33a5f 100644
--- a/Library/Homebrew/test/extend/kernel_spec.rb
+++ b/Library/Homebrew/test/extend/kernel_spec.rb
@@ -230,12 +230,12 @@ def esc(code)
       expect do
         odeprecated(
           "method", "replacement",
-          caller:  ["#{HOMEBREW_LIBRARY}/Taps/homebrew/homebrew-core/"],
+          caller:  ["#{HOMEBREW_LIBRARY}/Taps/playbrew/homebrew-play/"],
           disable: true
         )
       end.to raise_error(
         MethodDeprecatedError,
-        %r{method.*replacement.*homebrew/core.*/Taps/homebrew/homebrew-core/}m,
+        %r{method.*replacement.*playbrew/homebrew-play.*/Taps/playbrew/homebrew-play/}m,
       )
     end
   end
diff --git a/Library/Homebrew/utils/github/actions.rb b/Library/Homebrew/utils/github/actions.rb
index 9e20bef10bfedb..6306adbba03181 100644
--- a/Library/Homebrew/utils/github/actions.rb
+++ b/Library/Homebrew/utils/github/actions.rb
@@ -35,6 +35,25 @@ def self.format_multiline_string(name, value)
       EOS
     end
 
+    sig { returns(T::Boolean) }
+    def self.env_set?
+      # Don't print annotations during tests because it's too messy to handle.
+      return false if ENV.fetch("HOMEBREW_TESTS", false)
+
+      ENV.fetch("GITHUB_ACTIONS", false).present?
+    end
+
+    sig {
+      params(
+        type: Symbol, message: String,
+        file: T.nilable(T.any(String, Pathname)),
+        line: T.nilable(Integer)
+      ).void
+    }
+    def self.puts_annotation_if_env_set(type, message, file: nil, line: nil)
+      puts Annotation.new(type, message) if env_set?
+    end
+
     # Helper class for formatting annotations on GitHub Actions.
     class Annotation
       ANNOTATION_TYPES = [:notice, :warning, :error].freeze
@@ -52,7 +71,7 @@ def self.path_relative_to_workspace(path)
         params(
           type:       Symbol,
           message:    String,
-          file:       T.any(String, Pathname),
+          file:       T.nilable(T.any(String, Pathname)),
           title:      T.nilable(String),
           line:       T.nilable(Integer),
           end_line:   T.nilable(Integer),
@@ -60,12 +79,12 @@ def self.path_relative_to_workspace(path)
           end_column: T.nilable(Integer),
         ).void
       }
-      def initialize(type, message, file:, title: nil, line: nil, end_line: nil, column: nil, end_column: nil)
+      def initialize(type, message, file: nil, title: nil, line: nil, end_line: nil, column: nil, end_column: nil)
         raise ArgumentError, "Unsupported type: #{type.inspect}" if ANNOTATION_TYPES.exclude?(type)
 
         @type = type
         @message = Tty.strip_ansi(message)
-        @file = self.class.path_relative_to_workspace(file)
+        @file = self.class.path_relative_to_workspace(file) if file.present?
         @title = Tty.strip_ansi(title) if title
         @line = Integer(line) if line
         @end_line = Integer(end_line) if end_line
@@ -76,15 +95,17 @@ def initialize(type, message, file:, title: nil, line: nil, end_line: nil, colum
       sig { returns(String) }
       def to_s
         metadata = @type.to_s
-        metadata << " file=#{Actions.escape(@file.to_s)}"
+        if @file
+          metadata << " file=#{Actions.escape(@file.to_s)}"
 
-        if @line
-          metadata << ",line=#{@line}"
-          metadata << ",endLine=#{@end_line}" if @end_line
+          if @line
+            metadata << ",line=#{@line}"
+            metadata << ",endLine=#{@end_line}" if @end_line
 
-          if @column
-            metadata << ",col=#{@column}"
-            metadata << ",endColumn=#{@end_column}" if @end_column
+            if @column
+              metadata << ",col=#{@column}"
+              metadata << ",endColumn=#{@end_column}" if @end_column
+            end
           end
         end
 
@@ -97,6 +118,8 @@ def to_s
       # the `GITHUB_WORKSPACE` directory or if no `file` is specified.
       sig { returns(T::Boolean) }
       def relevant?
+        return true if @file.blank?
+
         @file.descend.next.to_s != ".."
       end
     end