diff --git a/Library/Homebrew/cask/download.rb b/Library/Homebrew/cask/download.rb
index a5b3d31f74..4c80eb2628 100644
--- a/Library/Homebrew/cask/download.rb
+++ b/Library/Homebrew/cask/download.rb
@@ -19,9 +19,10 @@ module Cask
       @quarantine = quarantine
     end
 
-    def fetch(verify_download_integrity: true)
+    def fetch(quiet: nil, verify_download_integrity: true, timeout: nil)
       downloaded_path = begin
-        downloader.fetch
+        downloader.shutup! if quiet
+        downloader.fetch(timeout: timeout)
         downloader.cached_location
       rescue => e
         error = CaskError.new("Download failed on Cask '#{cask}' with message: #{e}")
@@ -40,8 +41,8 @@ module Cask
       end
     end
 
-    def time_file_size
-      downloader.resolved_time_file_size
+    def time_file_size(timeout: nil)
+      downloader.resolved_time_file_size(timeout: timeout)
     end
 
     def clear_cache
diff --git a/Library/Homebrew/cask/installer.rb b/Library/Homebrew/cask/installer.rb
index 4b50d16279..4b1395786b 100644
--- a/Library/Homebrew/cask/installer.rb
+++ b/Library/Homebrew/cask/installer.rb
@@ -62,13 +62,15 @@ module Cask
       EOS
     end
 
-    def fetch
+    sig { params(quiet: T.nilable(T::Boolean), timeout: T.nilable(T.any(Integer, Float))).void }
+    def fetch(quiet: nil, timeout: nil)
       odebug "Cask::Installer#fetch"
 
       verify_has_sha if require_sha? && !force?
-      satisfy_dependencies
 
-      download
+      download(quiet: quiet, timeout: timeout)
+
+      satisfy_dependencies
     end
 
     def stage
@@ -162,9 +164,10 @@ module Cask
       @downloader ||= Download.new(@cask, quarantine: quarantine?)
     end
 
-    sig { returns(Pathname) }
-    def download
-      @download ||= downloader.fetch(verify_download_integrity: @verify_download_integrity)
+    sig { params(quiet: T.nilable(T::Boolean), timeout: T.nilable(T.any(Integer, Float))).returns(Pathname) }
+    def download(quiet: nil, timeout: nil)
+      @download ||= downloader.fetch(quiet: quiet, verify_download_integrity: @verify_download_integrity,
+timeout: timeout)
     end
 
     def verify_has_sha
@@ -179,7 +182,7 @@ module Cask
 
     def primary_container
       @primary_container ||= begin
-        downloaded_path = download
+        downloaded_path = download(quiet: true)
         UnpackStrategy.detect(downloaded_path, type: @cask.container&.type, merge_xattrs: true)
       end
     end
diff --git a/Library/Homebrew/download_strategy.rb b/Library/Homebrew/download_strategy.rb
index bf52bc08a2..94db909836 100644
--- a/Library/Homebrew/download_strategy.rb
+++ b/Library/Homebrew/download_strategy.rb
@@ -15,6 +15,9 @@ require "utils/curl"
 
 require "github_packages"
 
+require "extend/time"
+using TimeRemaining
+
 # @abstract Abstract superclass for all download strategies.
 #
 # @api private
@@ -52,7 +55,7 @@ class AbstractDownloadStrategy
   # Download and cache the resource at {#cached_location}.
   #
   # @api public
-  def fetch; end
+  def fetch(timeout: nil); end
 
   # Disable any output during downloading.
   #
@@ -176,18 +179,20 @@ class VCSDownloadStrategy < AbstractDownloadStrategy
   # Download and cache the repository at {#cached_location}.
   #
   # @api public
-  def fetch
+  def fetch(timeout: nil)
+    end_time = Time.now + timeout if timeout
+
     ohai "Cloning #{url}"
 
     if cached_location.exist? && repo_valid?
       puts "Updating #{cached_location}"
-      update
+      update(timeout: timeout)
     elsif cached_location.exist?
       puts "Removing invalid repository from cache"
       clear_cache
-      clone_repo
+      clone_repo(timeout: end_time)
     else
-      clone_repo
+      clone_repo(timeout: end_time)
     end
 
     version.update_commit(last_commit) if head?
@@ -232,9 +237,11 @@ class VCSDownloadStrategy < AbstractDownloadStrategy
     raise NotImplementedError
   end
 
-  def clone_repo; end
+  sig { params(timeout: T.nilable(Time)).void }
+  def clone_repo(timeout: nil); end
 
-  def update; end
+  sig { params(timeout: T.nilable(Time)).void }
+  def update(timeout: nil); end
 
   def current_revision; end
 
@@ -353,7 +360,9 @@ class CurlDownloadStrategy < AbstractFileDownloadStrategy
   # Download and cache the file at {#cached_location}.
   #
   # @api public
-  def fetch
+  def fetch(timeout: nil)
+    end_time = Time.now + timeout if timeout
+
     download_lock = LockFile.new(temporary_path.basename)
     download_lock.lock
 
@@ -364,7 +373,7 @@ class CurlDownloadStrategy < AbstractFileDownloadStrategy
 
       ohai "Downloading #{url}"
 
-      resolved_url, _, url_time, = resolve_url_basename_time_file_size(url)
+      resolved_url, _, url_time, = resolve_url_basename_time_file_size(url, timeout: end_time&.remaining!)
 
       fresh = if cached_location.exist? && url_time
         url_time <= cached_location.mtime
@@ -378,7 +387,7 @@ class CurlDownloadStrategy < AbstractFileDownloadStrategy
         puts "Already downloaded: #{cached_location}"
       else
         begin
-          _fetch(url: url, resolved_url: resolved_url)
+          _fetch(url: url, resolved_url: resolved_url, timeout: end_time&.remaining!)
         rescue ErrorDuringExecution
           raise CurlDownloadStrategyError, url
         end
@@ -395,6 +404,8 @@ class CurlDownloadStrategy < AbstractFileDownloadStrategy
 
       puts "Trying a mirror..."
       retry
+    rescue Timeout::Error => e
+      raise Timeout::Error, "Timed out downloading #{self.url}: #{e}"
     end
   ensure
     download_lock&.unlock
@@ -406,19 +417,19 @@ class CurlDownloadStrategy < AbstractFileDownloadStrategy
     rm_rf(temporary_path)
   end
 
-  def resolved_time_file_size
-    _, _, time, file_size = resolve_url_basename_time_file_size(url)
+  def resolved_time_file_size(timeout: nil)
+    _, _, time, file_size = resolve_url_basename_time_file_size(url, timeout: timeout)
     [time, file_size]
   end
 
   private
 
-  def resolved_url_and_basename
-    resolved_url, basename, = resolve_url_basename_time_file_size(url)
+  def resolved_url_and_basename(timeout: nil)
+    resolved_url, basename, = resolve_url_basename_time_file_size(url, timeout: nil)
     [resolved_url, basename]
   end
 
-  def resolve_url_basename_time_file_size(url)
+  def resolve_url_basename_time_file_size(url, timeout: nil)
     @resolved_info_cache ||= {}
     return @resolved_info_cache[url] if @resolved_info_cache.include?(url)
 
@@ -426,7 +437,7 @@ class CurlDownloadStrategy < AbstractFileDownloadStrategy
       url = url.sub(%r{^((ht|f)tps?://)?}, "#{domain.chomp("/")}/")
     end
 
-    out, _, status= curl_output("--location", "--silent", "--head", "--request", "GET", url.to_s)
+    out, _, status= curl_output("--location", "--silent", "--head", "--request", "GET", url.to_s, timeout: timeout)
 
     lines = status.success? ? out.lines.map(&:chomp) : []
 
@@ -485,7 +496,7 @@ class CurlDownloadStrategy < AbstractFileDownloadStrategy
     @resolved_info_cache[url] = [redirect_url, basename, time, file_size]
   end
 
-  def _fetch(url:, resolved_url:)
+  def _fetch(url:, resolved_url:, timeout:)
     ohai "Downloading from #{resolved_url}" if url != resolved_url
 
     if Homebrew::EnvConfig.no_insecure_redirect? &&
@@ -494,7 +505,7 @@ class CurlDownloadStrategy < AbstractFileDownloadStrategy
       raise CurlDownloadStrategyError, url
     end
 
-    curl_download resolved_url, to: temporary_path
+    curl_download resolved_url, to: temporary_path, timeout: timeout
   end
 
   # Curl options to be always passed to curl,
@@ -567,9 +578,9 @@ class CurlApacheMirrorDownloadStrategy < CurlDownloadStrategy
     @combined_mirrors = [*@mirrors, *backup_mirrors]
   end
 
-  def resolve_url_basename_time_file_size(url)
+  def resolve_url_basename_time_file_size(url, timeout: nil)
     if url == self.url
-      super("#{apache_mirrors["preferred"]}#{apache_mirrors["path_info"]}")
+      super("#{apache_mirrors["preferred"]}#{apache_mirrors["path_info"]}", timeout: timeout)
     else
       super
     end
@@ -592,7 +603,7 @@ end
 class CurlPostDownloadStrategy < CurlDownloadStrategy
   private
 
-  def _fetch(url:, resolved_url:)
+  def _fetch(url:, resolved_url:, timeout:)
     args = if meta.key?(:data)
       escape_data = ->(d) { ["-d", URI.encode_www_form([d])] }
       [url, *meta[:data].flat_map(&escape_data)]
@@ -601,7 +612,7 @@ class CurlPostDownloadStrategy < CurlDownloadStrategy
       query.nil? ? [url, "-X", "POST"] : [url, "-d", query]
     end
 
-    curl_download(*args, to: temporary_path)
+    curl_download(*args, to: temporary_path, timeout: timeout)
   end
 end
 
@@ -641,7 +652,7 @@ class SubversionDownloadStrategy < VCSDownloadStrategy
   # Download and cache the repository at {#cached_location}.
   #
   # @api public
-  def fetch
+  def fetch(timeout: nil)
     if @url.chomp("/") != repo_url || !silent_command("svn", args: ["switch", @url, cached_location]).success?
       clear_cache
     end
@@ -682,7 +693,11 @@ class SubversionDownloadStrategy < VCSDownloadStrategy
     end
   end
 
-  def fetch_repo(target, url, revision = nil, ignore_externals: false)
+  sig {
+    params(target: Pathname, url: String, revision: T.nilable(String), ignore_externals: T::Boolean,
+   timeout: T.nilable(Time)).void
+  }
+  def fetch_repo(target, url, revision = nil, ignore_externals: false, timeout: nil)
     # Use "svn update" when the repository already exists locally.
     # This saves on bandwidth and will have a similar effect to verifying the
     # cache as it will make any changes to get the right revision.
@@ -702,9 +717,9 @@ class SubversionDownloadStrategy < VCSDownloadStrategy
     end
 
     if target.directory?
-      command!("svn", args: ["update", *args], chdir: target.to_s)
+      command! "svn", args: ["update", *args], chdir: target.to_s, timeout: timeout&.remaining
     else
-      command!("svn", args: ["checkout", url, target, *args])
+      command! "svn", args: ["checkout", url, target, *args], timeout: timeout&.remaining
     end
   end
 
@@ -717,20 +732,22 @@ class SubversionDownloadStrategy < VCSDownloadStrategy
     (cached_location/".svn").directory?
   end
 
-  def clone_repo
+  sig { params(timeout: T.nilable(Time)).void }
+  def clone_repo(timeout: nil)
     case @ref_type
     when :revision
-      fetch_repo cached_location, @url, @ref
+      fetch_repo cached_location, @url, @ref, timeout: timeout
     when :revisions
       # nil is OK for main_revision, as fetch_repo will then get latest
       main_revision = @ref[:trunk]
-      fetch_repo cached_location, @url, main_revision, ignore_externals: true
+      fetch_repo cached_location, @url, main_revision, ignore_externals: true, timeout: timeout
 
       externals do |external_name, external_url|
-        fetch_repo cached_location/external_name, external_url, @ref[external_name], ignore_externals: true
+        fetch_repo cached_location/external_name, external_url, @ref[external_name], ignore_externals: true,
+                                                                                     timeout:          timeout
       end
     else
-      fetch_repo cached_location, @url
+      fetch_repo cached_location, @url, timeout: timeout
     end
   end
   alias update clone_repo
@@ -779,12 +796,13 @@ class GitDownloadStrategy < VCSDownloadStrategy
     0
   end
 
-  def update
+  sig { params(timeout: T.nilable(Time)).void }
+  def update(timeout: nil)
     config_repo
-    update_repo
-    checkout
+    update_repo(timeout: timeout)
+    checkout(timeout: timeout)
     reset
-    update_submodules if submodules?
+    update_submodules(timeout: timeout) if submodules?
   end
 
   def shallow_clone?
@@ -845,6 +863,7 @@ class GitDownloadStrategy < VCSDownloadStrategy
     end
   end
 
+  sig { void }
   def config_repo
     command! "git",
              args:  ["config", "remote.origin.url", @url],
@@ -857,35 +876,42 @@ class GitDownloadStrategy < VCSDownloadStrategy
              chdir: cached_location
   end
 
-  def update_repo
+  sig { params(timeout: T.nilable(Time)).void }
+  def update_repo(timeout: nil)
     return if @ref_type != :branch && ref?
 
     if !shallow_clone? && shallow_dir?
       command! "git",
-               args:  ["fetch", "origin", "--unshallow"],
-               chdir: cached_location
+               args:    ["fetch", "origin", "--unshallow"],
+               chdir:   cached_location,
+               timeout: timeout&.remaining
     else
       command! "git",
-               args:  ["fetch", "origin"],
-               chdir: cached_location
+               args:    ["fetch", "origin"],
+               chdir:   cached_location,
+               timeout: timeout&.remaining
     end
   end
 
-  def clone_repo
-    command! "git", args: clone_args
+  sig { params(timeout: T.nilable(Time)).void }
+  def clone_repo(timeout: nil)
+    command! "git", args: clone_args, timeout: timeout&.remaining
 
     command! "git",
-             args:  ["config", "homebrew.cacheversion", cache_version],
-             chdir: cached_location
-    checkout
-    update_submodules if submodules?
+             args:    ["config", "homebrew.cacheversion", cache_version],
+             chdir:   cached_location,
+             timeout: timeout&.remaining
+    checkout(timeout: timeout)
+    update_submodules(timeout: timeout) if submodules?
   end
 
-  def checkout
+  sig { params(timeout: T.nilable(Time)).void }
+  def checkout(timeout: nil)
     ohai "Checking out #{@ref_type} #{@ref}" if @ref_type && @ref
-    command! "git", args: ["checkout", "-f", @ref, "--"], chdir: cached_location
+    command! "git", args: ["checkout", "-f", @ref, "--"], chdir: cached_location, timeout: timeout&.remaining
   end
 
+  sig { void }
   def reset
     ref = case @ref_type
     when :branch
@@ -899,13 +925,16 @@ class GitDownloadStrategy < VCSDownloadStrategy
              chdir: cached_location
   end
 
-  def update_submodules
+  sig { params(timeout: T.nilable(Time)).void }
+  def update_submodules(timeout: nil)
     command! "git",
-             args:  ["submodule", "foreach", "--recursive", "git submodule sync"],
-             chdir: cached_location
+             args:    ["submodule", "foreach", "--recursive", "git submodule sync"],
+             chdir:   cached_location,
+             timeout: timeout&.remaining
     command! "git",
-             args:  ["submodule", "update", "--init", "--recursive"],
-             chdir: cached_location
+             args:    ["submodule", "update", "--init", "--recursive"],
+             chdir:   cached_location,
+             timeout: timeout&.remaining
     fix_absolute_submodule_gitdir_references!
   end
 
@@ -1057,19 +1086,23 @@ class CVSDownloadStrategy < VCSDownloadStrategy
     "-Q" unless verbose?
   end
 
-  def clone_repo
+  sig { params(timeout: T.nilable(Time)).void }
+  def clone_repo(timeout: nil)
     # Login is only needed (and allowed) with pserver; skip for anoncvs.
-    command! "cvs", args: [*quiet_flag, "-d", @url, "login"] if @url.include? "pserver"
+    command! "cvs", args: [*quiet_flag, "-d", @url, "login"], timeout: timeout&.remaining if @url.include? "pserver"
 
     command! "cvs",
-             args:  [*quiet_flag, "-d", @url, "checkout", "-d", cached_location.basename, @module],
-             chdir: cached_location.dirname
+             args:    [*quiet_flag, "-d", @url, "checkout", "-d", cached_location.basename, @module],
+             chdir:   cached_location.dirname,
+             timeout: timeout&.remaining
   end
 
-  def update
+  sig { params(timeout: T.nilable(Time)).void }
+  def update(timeout: nil)
     command! "cvs",
-             args:  [*quiet_flag, "update"],
-             chdir: cached_location
+             args:    [*quiet_flag, "update"],
+             chdir:   cached_location,
+             timeout: timeout&.remaining
   end
 
   def split_url(in_url)
@@ -1121,12 +1154,14 @@ class MercurialDownloadStrategy < VCSDownloadStrategy
     (cached_location/".hg").directory?
   end
 
-  def clone_repo
-    command! "hg", args: ["clone", @url, cached_location]
+  sig { params(timeout: T.nilable(Time)).void }
+  def clone_repo(timeout: nil)
+    command! "hg", args: ["clone", @url, cached_location], timeout: timeout&.remaining
   end
 
-  def update
-    command! "hg", args: ["--cwd", cached_location, "pull", "--update"]
+  sig { params(timeout: T.nilable(Time)).void }
+  def update(timeout: nil)
+    command! "hg", args: ["--cwd", cached_location, "pull", "--update"], timeout: timeout&.remaining
 
     update_args = if @ref_type && @ref
       ohai "Checking out #{@ref_type} #{@ref}"
@@ -1135,7 +1170,7 @@ class MercurialDownloadStrategy < VCSDownloadStrategy
       ["--clean"]
     end
 
-    command! "hg", args: ["--cwd", cached_location, "update", *update_args]
+    command! "hg", args: ["--cwd", cached_location, "update", *update_args], timeout: timeout&.remaining
   end
 end
 
@@ -1184,16 +1219,20 @@ class BazaarDownloadStrategy < VCSDownloadStrategy
     (cached_location/".bzr").directory?
   end
 
-  def clone_repo
+  sig { params(timeout: T.nilable(Time)).void }
+  def clone_repo(timeout: nil)
     # "lightweight" means history-less
     command! "bzr",
-             args: ["checkout", "--lightweight", @url, cached_location]
+             args:    ["checkout", "--lightweight", @url, cached_location],
+             timeout: timeout&.remaining
   end
 
-  def update
+  sig { params(timeout: T.nilable(Time)).void }
+  def update(timeout: nil)
     command! "bzr",
-             args:  ["update"],
-             chdir: cached_location
+             args:    ["update"],
+             chdir:   cached_location,
+             timeout: timeout&.remaining
   end
 end
 
@@ -1236,12 +1275,14 @@ class FossilDownloadStrategy < VCSDownloadStrategy
     "fossil"
   end
 
-  def clone_repo
-    silent_command!("fossil", args: ["clone", @url, cached_location])
+  sig { params(timeout: T.nilable(Time)).void }
+  def clone_repo(timeout: nil)
+    silent_command! "fossil", args: ["clone", @url, cached_location], timeout: timeout&.remaining
   end
 
-  def update
-    silent_command!("fossil", args: ["pull", "-R", cached_location])
+  sig { params(timeout: T.nilable(Time)).void }
+  def update(timeout: nil)
+    silent_command! "fossil", args: ["pull", "-R", cached_location], timeout: timeout&.remaining
   end
 end
 
diff --git a/Library/Homebrew/extend/time.rb b/Library/Homebrew/extend/time.rb
new file mode 100644
index 0000000000..81779cd8dc
--- /dev/null
+++ b/Library/Homebrew/extend/time.rb
@@ -0,0 +1,18 @@
+# typed: false
+# frozen_string_literal: true
+
+module TimeRemaining
+  refine Time do
+    def remaining
+      [0, self - Time.now].max
+    end
+
+    def remaining!
+      r = remaining
+
+      raise Timeout::Error if r <= 0
+
+      r
+    end
+  end
+end
diff --git a/Library/Homebrew/sorbet/plugins/using.rb b/Library/Homebrew/sorbet/plugins/using.rb
index e1bf761b29..288c4c6c44 100644
--- a/Library/Homebrew/sorbet/plugins/using.rb
+++ b/Library/Homebrew/sorbet/plugins/using.rb
@@ -28,4 +28,16 @@ when "HashValidator"
       def assert_valid_keys!(*valid_keys); end
     end
   RUBY
+when "TimeRemaining"
+  puts <<-RUBY
+    # typed: strict
+
+    class ::Time
+      sig { returns(T.any(Integer, Float)) }
+      def remaining; end
+
+      sig { returns(T.any(Integer, Float)) }
+      def remaining!; end
+    end
+  RUBY
 end
diff --git a/Library/Homebrew/system_command.rb b/Library/Homebrew/system_command.rb
index 7d049c0c62..952564ffb6 100644
--- a/Library/Homebrew/system_command.rb
+++ b/Library/Homebrew/system_command.rb
@@ -10,13 +10,15 @@ require "extend/io"
 require "extend/predicable"
 require "extend/hash_validator"
 
+require "extend/time"
+
 # Class for running sub-processes and capturing their output and exit status.
 #
 # @api private
 class SystemCommand
   extend T::Sig
 
-  using HashValidator
+  using TimeRemaining
 
   # Helper functions for calling {SystemCommand.run}.
   module Mixin
@@ -78,10 +80,24 @@ class SystemCommand
       verbose:      T.nilable(T::Boolean),
       secrets:      T.any(String, T::Array[String]),
       chdir:        T.any(String, Pathname),
+      timeout:      T.nilable(T.any(Integer, Float)),
     ).void
   }
-  def initialize(executable, args: [], sudo: false, env: {}, input: [], must_succeed: false,
-                 print_stdout: false, print_stderr: true, debug: nil, verbose: nil, secrets: [], chdir: T.unsafe(nil))
+  def initialize(
+    executable,
+    args: [],
+    sudo: false,
+    env: {},
+    input: [],
+    must_succeed: false,
+    print_stdout: false,
+    print_stderr: true,
+    debug: nil,
+    verbose: false,
+    secrets: [],
+    chdir: T.unsafe(nil),
+    timeout: nil
+  )
     require "extend/ENV"
     @executable = executable
     @args = args
@@ -100,6 +116,7 @@ class SystemCommand
     @verbose = verbose
     @secrets = (Array(secrets) + ENV.sensitive_environment.values).uniq
     @chdir = chdir
+    @timeout = timeout
   end
 
   sig { returns(T::Array[String]) }
@@ -197,10 +214,14 @@ class SystemCommand
 
   sig { params(sources: T::Array[IO], _block: T.proc.params(type: Symbol, line: String).void).void }
   def each_line_from(sources, &_block)
-    loop do
-      readable_sources, = IO.select(sources)
+    end_time = Time.now + @timeout if @timeout
 
-      readable_sources = T.must(readable_sources).reject(&:eof?)
+    loop do
+      select_timeout = end_time&.remaining!
+      readable_sources, = IO.select(sources, [], [], select_timeout)
+      raise Timeout::Error if readable_sources.nil?
+
+      readable_sources = readable_sources.reject(&:eof?)
 
       break if readable_sources.empty?
 
diff --git a/Library/Homebrew/utils/curl.rb b/Library/Homebrew/utils/curl.rb
index 8e2a798ed3..f6d7cbea75 100644
--- a/Library/Homebrew/utils/curl.rb
+++ b/Library/Homebrew/utils/curl.rb
@@ -3,11 +3,15 @@
 
 require "open3"
 
+require "extend/time"
+
 module Utils
   # Helper function for interacting with `curl`.
   #
   # @api private
   module Curl
+    using TimeRemaining
+
     module_function
 
     def curl_executable
@@ -49,14 +53,20 @@ module Utils
         args << "--silent" unless $stdout.tty?
       end
 
+      args << "--connect-timeout" << connect_timeout.round(3) if options[:connect_timeout]
+      args << "--max-time" << max_time.round(3) if options[:max_time]
       args << "--retry" << Homebrew::EnvConfig.curl_retries unless options[:retry] == false
+      args << "--retry-max-time" << retry_max_time.round if options[:retry_max_time]
 
       args + extra_args
     end
 
     def curl_with_workarounds(
-      *args, secrets: nil, print_stdout: nil, print_stderr: nil, debug: nil, verbose: nil, env: {}, **options
+      *args,
+      secrets: nil, print_stdout: nil, print_stderr: nil, debug: nil, verbose: nil, env: {}, timeout: nil, **options
     )
+      end_time = Time.now + timeout if timeout
+
       command_options = {
         secrets:      secrets,
         print_stdout: print_stdout,
@@ -68,14 +78,22 @@ module Utils
       # SSL_CERT_FILE can be incorrectly set by users or portable-ruby and screw
       # with SSL downloads so unset it here.
       result = system_command curl_executable,
-                              args: curl_args(*args, **options),
-                              env:  { "SSL_CERT_FILE" => nil }.merge(env),
+                              args:    curl_args(*args, **options),
+                              env:     { "SSL_CERT_FILE" => nil }.merge(env),
+                              timeout: end_time&.remaining,
                               **command_options
 
       return result if result.success? || !args.exclude?("--http1.1")
 
+      raise Timeout::Error, result.stderr.chomp if result.status.exitstatus == 28
+
       # Error in the HTTP2 framing layer
-      return curl_with_workarounds(*args, "--http1.1", **command_options, **options) if result.status.exitstatus == 16
+      if result.status.exitstatus == 16
+        return curl_with_workarounds(
+          *args, "--http1.1",
+          timeout: end_time&.remaining, **command_options, **options
+        )
+      end
 
       # This is a workaround for https://github.com/curl/curl/issues/1618.
       if result.status.exitstatus == 56 # Unexpected EOF