install/upgrade: add --non-interactive and --timeout-wait-for-user; env: HOMEBREW_NON_INTERACTIVE, HOMEBREW_PROMPT_TIMEOUT_SECS; system_command: non-interactive sudo and prompt-aware timeout with skip reporting

Author: rehkad

Library/Homebrew/cmd/install.rb

@@ -47,6 +47,12 @@ class InstallCmd < AbstractCommand
                description: "Ask for confirmation before downloading and installing formulae. " \
                             "Print download and install sizes of bottles and dependencies.",
                env:         :ask
+        switch "--non-interactive",
+               description: "Fail fast on any interactive prompt and use non-interactive sudo where applicable.",
+               env:         :non_interactive
+        flag "--timeout-wait-for-user=",
+             description: "Wait this many seconds when an interactive prompt is detected; then skip the item.",
+             env:         :prompt_timeout_secs
         [
           [:switch, "--formula", "--formulae", {
             description: "Treat all named arguments as formulae.",
@@ -176,6 +182,14 @@ class InstallCmd < AbstractCommand
 
       sig { override.void }
       def run
+        # Apply context for non-interactive/verbosity here so lower layers can query Context
+        if args.non_interactive?
+          ENV["HOMEBREW_NON_INTERACTIVE"] = "1"
+        end
+        if args.timeout_wait_for_user.present?
+          ENV["HOMEBREW_PROMPT_TIMEOUT_SECS"] = args.timeout_wait_for_user
+        end
+
         if args.env.present?
           # Can't use `replacement: false` because `install_args` are used by
           # `build.rb`. Instead, `hide_from_man_page` and don't do anything with
@@ -267,7 +281,7 @@ def run
           end
 
           new_casks.each do |cask|
-            Cask::Installer.new(
+            installer = Cask::Installer.new(
               cask,
               adopt:          args.adopt?,
               binaries:       args.binaries?,
@@ -277,7 +291,14 @@ def run
               require_sha:    args.require_sha?,
               skip_cask_deps: args.skip_cask_deps?,
               verbose:        args.verbose?,
-            ).install
+            )
+            begin
+              installer.install
+            rescue Timeout::Error => e
+              opoo "Timed out waiting for user input in cask #{cask.full_name}. Skipping."
+              Homebrew.messages.record_skipped_prompt(cask.full_name, e.message)
+              next
+            end
           end
 
           if !Homebrew::EnvConfig.no_install_upgrade? && installed_casks.any?

Library/Homebrew/cmd/upgrade.rb

@@ -43,6 +43,12 @@ class UpgradeCmd < AbstractCommand
                description: "Ask for confirmation before downloading and upgrading formulae. " \
                             "Print download, install and net install sizes of bottles and dependencies.",
                env:         :ask
+        switch "--non-interactive",
+               description: "Fail fast on any interactive prompt and use non-interactive sudo where applicable.",
+               env:         :non_interactive
+        flag "--timeout-wait-for-user=",
+             description: "Wait this many seconds when an interactive prompt is detected; then skip the item.",
+             env:         :prompt_timeout_secs
         [
           [:switch, "--formula", "--formulae", {
             description: "Treat all named arguments as formulae. If no named arguments " \
@@ -125,6 +131,12 @@ class UpgradeCmd < AbstractCommand
 
       sig { override.void }
       def run
+        if args.non_interactive?
+          ENV["HOMEBREW_NON_INTERACTIVE"] = "1"
+        end
+        if args.timeout_wait_for_user.present?
+          ENV["HOMEBREW_PROMPT_TIMEOUT_SECS"] = args.timeout_wait_for_user
+        end
         if args.build_from_source? && args.named.empty?
           raise ArgumentError, "--build-from-source requires at least one formula"
         end
@@ -286,7 +298,8 @@ def upgrade_outdated_casks!(casks)
 
         Install.ask_casks casks if args.ask?
 
-        Cask::Upgrade.upgrade_casks!(
+        begin
+          Cask::Upgrade.upgrade_casks!(
           *casks,
           force:               args.force?,
           greedy:              args.greedy?,
@@ -300,7 +313,13 @@ def upgrade_outdated_casks!(casks)
           verbose:             args.verbose?,
           quiet:               args.quiet?,
           args:,
-        )
+          )
+        rescue Timeout::Error => e
+          # When multiple casks are processed, `upgrade_casks!` handles each sequentially
+          # Skips are recorded inside the installer loop where errors are rescued
+          opoo "Timed out waiting for user input while upgrading casks. Some items may be skipped."
+          Homebrew.messages.record_skipped_prompt("cask-upgrade", e.message)
+        end
       end
     end
   end

Library/Homebrew/env_config.rb

@@ -469,6 +469,16 @@ module EnvConfig
                       "fetching Git repositories over SSH.",
         default_text: "`~/.ssh/config`",
       },
+      HOMEBREW_NON_INTERACTIVE:                  {
+        description: "If set, treat Homebrew commands as non-interactive: use `sudo -n` when elevating and fail " \
+                     "immediately on any interactive prompt.",
+        boolean:     true,
+      },
+      HOMEBREW_PROMPT_TIMEOUT_SECS:              {
+        description: "If set, when an interactive prompt (e.g., sudo/password) is detected during installation, " \
+                     "wait this many seconds and then skip/fail the current item while continuing others. " \
+                     "Unset to wait indefinitely.",
+      },
       HOMEBREW_SUDO_THROUGH_SUDO_USER:           {
         description: "If set, Homebrew will use the `$SUDO_USER` environment variable to define the user to " \
                      "`sudo`(8) through when running `sudo`(8).",

Library/Homebrew/messages.rb

@@ -13,12 +13,16 @@ class Messages
   sig { returns(T::Array[T::Hash[String, Float]]) }
   attr_reader :install_times
 
+  sig { returns(T::Array[T::Hash[Symbol, String]]) }
+  attr_reader :skipped_prompts
+
   sig { void }
   def initialize
     @caveats = T.let([], T::Array[T::Hash[Symbol, Symbol]])
     @completions_and_elisp = T.let(Set.new, T::Set[String])
     @package_count = T.let(0, Integer)
     @install_times = T.let([], T::Array[T::Hash[String, Float]])
+    @skipped_prompts = T.let([], T::Array[T::Hash[Symbol, String]])
   end
 
   sig { params(package: String, caveats: T.any(String, Caveats)).void }
@@ -40,9 +44,25 @@ def package_installed(package, elapsed_time)
   sig { params(force_caveats: T::Boolean, display_times: T::Boolean).void }
   def display_messages(force_caveats: false, display_times: false)
     display_caveats(force: force_caveats)
+    display_skipped_prompts
     display_install_times if display_times
   end
 
+  sig { params(package: String, reason: String).void }
+  def record_skipped_prompt(package, reason)
+    @skipped_prompts.push(package:, reason:)
+  end
+
+  sig { void }
+  def display_skipped_prompts
+    return if @skipped_prompts.empty?
+
+    oh1 "Skipped items due to interactive prompts"
+    @skipped_prompts.each do |entry|
+      puts "#{entry[:package]}: #{entry[:reason]}"
+    end
+  end
+
   sig { params(force: T::Boolean).void }
   def display_caveats(force: false)
     return if @package_count.zero?

Library/Homebrew/system_command.rb

@@ -48,6 +48,19 @@ def run!
 
     @output = []
 
+    @prompt_timeout_secs = nil
+    begin
+      prompt_timeout_env = Homebrew::EnvConfig.prompt_timeout_secs
+      if prompt_timeout_env && !prompt_timeout_env.strip.empty?
+        @prompt_timeout_secs = Integer(prompt_timeout_env) rescue Float(prompt_timeout_env)
+      end
+    rescue ArgumentError, TypeError
+      @prompt_timeout_secs = nil
+    end
+
+    @prompt_detected_at = nil
+    @terminated_due_to_prompt_timeout = false
+
     each_output_line do |type, line|
       case type
       when :stdout
@@ -67,9 +80,17 @@ def run!
         end
         @output << [:stderr, line]
       end
+
+      if @prompt_timeout_secs
+        # Detect common interactive prompt patterns
+        if line =~ /[Pp]assword:/ || line.include?("a password is required") || line =~ /installer: .*authorization/i
+          @prompt_detected_at ||= Time.now
+        end
+      end
     end
 
     result = Result.new(command, @output, @status, secrets: @secrets)
+    raise Timeout::Error, "Interactive prompt timeout" if @terminated_due_to_prompt_timeout
     result.assert_success! if must_succeed?
     result
   end
@@ -199,6 +220,7 @@ def homebrew_sudo_user
   sig { returns(T::Array[String]) }
   def sudo_prefix
     askpass_flags = ENV.key?("SUDO_ASKPASS") ? ["-A"] : []
+    non_interactive_flags = Homebrew::EnvConfig.non_interactive? ? ["-n"] : []
     user_flags = []
     if Homebrew::EnvConfig.sudo_through_sudo_user?
       if homebrew_sudo_user.blank?
@@ -211,7 +233,7 @@ def sudo_prefix
                      "--", "/usr/bin/sudo"]
     end
     user_flags += ["-u", "root"] if sudo_as_root?
-    ["/usr/bin/sudo", *user_flags, *askpass_flags, "-E", *env_args, "--"]
+    ["/usr/bin/sudo", *user_flags, *askpass_flags, *non_interactive_flags, "-E", *env_args, "--"]
   end
 
   sig { returns(T::Array[String]) }
@@ -252,6 +274,29 @@ def each_output_line(&block)
 
     raw_stdin, raw_stdout, raw_stderr, raw_wait_thr = exec3(env, executable, *args, **options)
 
+    monitor_thread = nil
+    if @prompt_timeout_secs
+      monitor_thread = Thread.new do
+        loop do
+          break unless raw_wait_thr.alive?
+          if @prompt_detected_at && (Time.now - @prompt_detected_at) >= @prompt_timeout_secs
+            begin
+              # Try TERM first, then KILL if needed
+              Process.kill("TERM", raw_wait_thr.pid)
+              sleep 0.5
+              Process.kill("KILL", raw_wait_thr.pid) if raw_wait_thr.alive?
+            rescue StandardError
+              # ignore
+            ensure
+              @terminated_due_to_prompt_timeout = true
+            end
+            break
+          end
+          sleep 0.2
+        end
+      end
+    end
+
     write_input_to(raw_stdin)
     raw_stdin.close_write
 
@@ -285,6 +330,7 @@ def each_output_line(&block)
       thread_done_queue << true
       line_thread.join
     end
+    monitor_thread&.kill
     raw_stdin&.close
     raw_stdout&.close
     raw_stderr&.close