diff --git a/Library/Homebrew/cmd/install.rb b/Library/Homebrew/cmd/install.rb
index ee695c1b43..60c272ac9e 100644
--- a/Library/Homebrew/cmd/install.rb
+++ b/Library/Homebrew/cmd/install.rb
@@ -310,9 +310,7 @@ module Homebrew
         Install.perform_preinstall_checks_once
         Install.check_cc_argv(args.cc)
 
-        Install.ask_formulae(installed_formulae, args: args) if args.ask?
-
-        Install.install_formulae(
+        formulae_installer = Install.formula_installers(
           installed_formulae,
           installed_on_request:       !args.as_dependency?,
           installed_as_dependency:    args.as_dependency?,
@@ -338,9 +336,10 @@ module Homebrew
           skip_link:                  args.skip_link?,
         )
 
-        Upgrade.check_installed_dependents(
+        dependants = Upgrade.dependants(
           installed_formulae,
           flags:                      args.flags_only,
+          ask:                        args.ask?,
           installed_on_request:       !args.as_dependency?,
           force_bottle:               args.force_bottle?,
           build_from_source_formulae: args.build_from_source_formulae,
@@ -354,6 +353,28 @@ module Homebrew
           dry_run:                    args.dry_run?,
         )
 
+        # Main block: if asking the user is enabled, show dependency and size information.
+        Install.ask_formulae(formulae_installer, dependants, args: args) if args.ask?
+
+        Install.install_formulae(formulae_installer,
+                                 dry_run: args.dry_run?,
+                                 verbose: args.verbose?)
+
+        Upgrade.upgrade_dependents(
+          dependants, installed_formulae,
+          flags:                      args.flags_only,
+          dry_run:                    args.dry_run?,
+          force_bottle:               args.force_bottle?,
+          build_from_source_formulae: args.build_from_source_formulae,
+          interactive:                args.interactive?,
+          keep_tmp:                   args.keep_tmp?,
+          debug_symbols:              args.debug_symbols?,
+          force:                      args.force?,
+          debug:                      args.debug?,
+          quiet:                      args.quiet?,
+          verbose:                    args.verbose?
+        )
+
         Cleanup.periodic_clean!(dry_run: args.dry_run?)
 
         Homebrew.messages.display_messages(display_times: args.display_times?)
diff --git a/Library/Homebrew/cmd/reinstall.rb b/Library/Homebrew/cmd/reinstall.rb
index f6361ec689..e0dd7182dc 100644
--- a/Library/Homebrew/cmd/reinstall.rb
+++ b/Library/Homebrew/cmd/reinstall.rb
@@ -130,16 +130,13 @@ module Homebrew
         unless formulae.empty?
           Install.perform_preinstall_checks_once
 
-          # If asking the user is enabled, show dependency and size information.
-          Install.ask_formulae(formulae, args: args) if args.ask?
-
-          formulae.each do |formula|
+          install_context = formulae.map do |formula|
             if formula.pinned?
               onoe "#{formula.full_name} is pinned. You must unpin it to reinstall."
               next
             end
             Migrator.migrate_if_needed(formula, force: args.force?)
-            Homebrew::Reinstall.reinstall_formula(
+            Homebrew::Reinstall.build_install_context(
               formula,
               flags:                      args.flags_only,
               force_bottle:               args.force_bottle?,
@@ -153,12 +150,12 @@ module Homebrew
               verbose:                    args.verbose?,
               git:                        args.git?,
             )
-            Cleanup.install_formula_clean!(formula)
           end
 
-          Upgrade.check_installed_dependents(
+          dependants = Upgrade.dependants(
             formulae,
             flags:                      args.flags_only,
+            ask:                        args.ask?,
             force_bottle:               args.force_bottle?,
             build_from_source_formulae: args.build_from_source_formulae,
             interactive:                args.interactive?,
@@ -169,6 +166,43 @@ module Homebrew
             quiet:                      args.quiet?,
             verbose:                    args.verbose?,
           )
+
+          formulae_installer = install_context.map(&:formula_installer)
+
+          # Main block: if asking the user is enabled, show dependency and size information.
+          Install.ask_formulae(formulae_installer, dependants, args: args) if args.ask?
+
+          install_context.each do |f|
+            Homebrew::Reinstall.reinstall_formula(
+              f,
+              flags:                      args.flags_only,
+              force_bottle:               args.force_bottle?,
+              build_from_source_formulae: args.build_from_source_formulae,
+              interactive:                args.interactive?,
+              keep_tmp:                   args.keep_tmp?,
+              debug_symbols:              args.debug_symbols?,
+              force:                      args.force?,
+              debug:                      args.debug?,
+              quiet:                      args.quiet?,
+              verbose:                    args.verbose?,
+              git:                        args.git?,
+            )
+            Cleanup.install_formula_clean!(f.formula)
+          end
+
+          Upgrade.upgrade_dependents(
+            dependants, formulae,
+            flags:                      args.flags_only,
+            force_bottle:               args.force_bottle?,
+            build_from_source_formulae: args.build_from_source_formulae,
+            interactive:                args.interactive?,
+            keep_tmp:                   args.keep_tmp?,
+            debug_symbols:              args.debug_symbols?,
+            force:                      args.force?,
+            debug:                      args.debug?,
+            quiet:                      args.quiet?,
+            verbose:                    args.verbose?
+          )
         end
 
         if casks.any?
diff --git a/Library/Homebrew/cmd/upgrade.rb b/Library/Homebrew/cmd/upgrade.rb
index d1880ea4bd..aa23543312 100644
--- a/Library/Homebrew/cmd/upgrade.rb
+++ b/Library/Homebrew/cmd/upgrade.rb
@@ -220,10 +220,7 @@ module Homebrew
 
         Install.perform_preinstall_checks_once
 
-        # Main block: if asking the user is enabled, show dependency and size information.
-        Install.ask_formulae(formulae_to_install, args: args) if args.ask?
-
-        Upgrade.upgrade_formulae(
+        formulae_installer = Upgrade.formula_installers(
           formulae_to_install,
           flags:                      args.flags_only,
           dry_run:                    args.dry_run?,
@@ -239,10 +236,33 @@ module Homebrew
           verbose:                    args.verbose?,
         )
 
-        Upgrade.check_installed_dependents(
+        dependants = Upgrade.dependants(
           formulae_to_install,
           flags:                      args.flags_only,
           dry_run:                    args.dry_run?,
+          ask:                        args.ask?,
+          force_bottle:               args.force_bottle?,
+          build_from_source_formulae: args.build_from_source_formulae,
+          interactive:                args.interactive?,
+          keep_tmp:                   args.keep_tmp?,
+          debug_symbols:              args.debug_symbols?,
+          force:                      args.force?,
+          debug:                      args.debug?,
+          quiet:                      args.quiet?,
+          verbose:                    args.verbose?,
+        )
+
+        # Main block: if asking the user is enabled, show dependency and size information.
+        Install.ask_formulae(formulae_installer, dependants, args: args) if args.ask?
+
+        Upgrade.upgrade_formulae(formulae_installer,
+                                 dry_run: args.dry_run?,
+                                 verbose: args.verbose?)
+
+        Upgrade.upgrade_dependents(
+          dependants, formulae_to_install,
+          flags:                      args.flags_only,
+          dry_run:                    args.dry_run?,
           force_bottle:               args.force_bottle?,
           build_from_source_formulae: args.build_from_source_formulae,
           interactive:                args.interactive?,
@@ -251,7 +271,7 @@ module Homebrew
           force:                      args.force?,
           debug:                      args.debug?,
           quiet:                      args.quiet?,
-          verbose:                    args.verbose?,
+          verbose:                    args.verbose?
         )
 
         true
diff --git a/Library/Homebrew/formula.rb b/Library/Homebrew/formula.rb
index 7b20a26dfc..ac85783f92 100644
--- a/Library/Homebrew/formula.rb
+++ b/Library/Homebrew/formula.rb
@@ -3207,11 +3207,11 @@ class Formula
     patchlist.select(&:external?).each(&:fetch)
   end
 
-  sig { void }
-  def fetch_bottle_tab
+  sig { params(quiet: T::Boolean).void }
+  def fetch_bottle_tab(quiet: false)
     return unless bottled?
 
-    T.must(bottle).fetch_tab
+    T.must(bottle).fetch_tab(quiet: quiet)
   end
 
   sig { returns(T::Hash[String, T.untyped]) }
diff --git a/Library/Homebrew/formula_installer.rb b/Library/Homebrew/formula_installer.rb
index 691abffc19..241863355f 100644
--- a/Library/Homebrew/formula_installer.rb
+++ b/Library/Homebrew/formula_installer.rb
@@ -1356,12 +1356,12 @@ on_request: installed_on_request?, options:)
     end
   end
 
-  sig { void }
-  def fetch_bottle_tab
+  sig { params(quiet: T::Boolean).void }
+  def fetch_bottle_tab(quiet: false)
     return if @fetch_bottle_tab
 
     begin
-      formula.fetch_bottle_tab
+      formula.fetch_bottle_tab(quiet: quiet)
       @bottle_tab_runtime_dependencies = formula.bottle_tab_attributes
                                                 .fetch("runtime_dependencies", []).then { |deps| deps || [] }
                                                 .each_with_object({}) { |dep, h| h[dep["full_name"]] = dep }
diff --git a/Library/Homebrew/install.rb b/Library/Homebrew/install.rb
index 7c614bcab1..48b9acb362 100644
--- a/Library/Homebrew/install.rb
+++ b/Library/Homebrew/install.rb
@@ -231,7 +231,7 @@ module Homebrew
         false
       end
 
-      def install_formulae(
+      def formula_installers(
         formulae_to_install,
         installed_on_request: true,
         installed_as_dependency: false,
@@ -256,11 +256,11 @@ module Homebrew
         skip_post_install: false,
         skip_link: false
       )
-        formula_installers = formulae_to_install.filter_map do |formula|
+        formulae_to_install.filter_map do |formula|
           Migrator.migrate_if_needed(formula, force:, dry_run:)
           build_options = formula.build
 
-          formula_installer = FormulaInstaller.new(
+          FormulaInstaller.new(
             formula,
             options:                    build_options.used_options,
             installed_on_request:,
@@ -285,24 +285,36 @@ module Homebrew
             skip_post_install:,
             skip_link:,
           )
-
-          begin
-            unless dry_run
-              formula_installer.prelude
-              formula_installer.fetch
-            end
-            formula_installer
-          rescue CannotInstallFormulaError => e
-            ofail e.message
-            nil
-          rescue UnsatisfiedRequirements, DownloadError, ChecksumMismatchError => e
-            ofail "#{formula}: #{e}"
-            nil
-          end
         end
+      end
 
+      def install_formulae(
+        formula_installers,
+        installed_on_request: true,
+        installed_as_dependency: false,
+        build_bottle: false,
+        force_bottle: false,
+        bottle_arch: nil,
+        ignore_deps: false,
+        only_deps: false,
+        include_test_formulae: [],
+        build_from_source_formulae: [],
+        cc: nil,
+        git: false,
+        interactive: false,
+        keep_tmp: false,
+        debug_symbols: false,
+        force: false,
+        overwrite: false,
+        debug: false,
+        quiet: false,
+        verbose: false,
+        dry_run: false,
+        skip_post_install: false,
+        skip_link: false
+      )
         if dry_run
-          if (formulae_name_to_install = formulae_to_install.map(&:name))
+          if (formulae_name_to_install = formula_installers.map(&:name))
             ohai "Would install #{Utils.pluralize("formula", formulae_name_to_install.count,
                                                   plural: "e", include_count: true)}:"
             puts formulae_name_to_install.join(" ")
@@ -315,6 +327,18 @@ module Homebrew
         end
 
         formula_installers.each do |fi|
+          begin
+            unless dry_run
+              fi.prelude
+              fi.fetch
+            end
+          rescue CannotInstallFormulaError => e
+            ofail e.message
+            next
+          rescue UnsatisfiedRequirements, DownloadError, ChecksumMismatchError => e
+            ofail "#{formula}: #{e}"
+            next
+          end
           install_formula(fi)
           Cleanup.install_formula_clean!(fi.formula)
         end
@@ -330,16 +354,17 @@ module Homebrew
       end
 
       # If asking the user is enabled, show dependency and size information.
-      def ask_formulae(formulae, args:)
-        return if formulae.empty?
+      def ask_formulae(formulae_installer, dependants, args:)
+        return if formulae_installer.empty?
+
+        formulae = collect_dependencies(formulae_installer, dependants)
 
         ohai "Looking for bottles..."
 
-        sized_formulae = compute_sized_formulae(formulae, args: args)
-        sizes = compute_total_sizes(sized_formulae, debug: args.debug?)
+        sizes = compute_total_sizes(formulae, debug: args.debug?)
 
-        puts "#{::Utils.pluralize("Formula", sized_formulae.count, plural: "e")} \
-(#{sized_formulae.count}): #{sized_formulae.join(", ")}\n\n"
+        puts "#{::Utils.pluralize("Formula", formulae.count, plural: "e")} \
+(#{formulae.count}): #{formulae.join(", ")}\n\n"
         puts "Download Size: #{disk_usage_readable(sizes[:download])}"
         puts "Install Size:  #{disk_usage_readable(sizes[:installed])}"
         puts "Net Install Size: #{disk_usage_readable(sizes[:net])}" if sizes[:net] != 0
@@ -411,41 +436,6 @@ module Homebrew
         end
       end
 
-      # Build a unique list of formulae to size by including:
-      # 1. The original formulae to install.
-      # 2. Their outdated dependents (subject to pruning criteria).
-      # 3. Optionally, any installed formula that depends on one of these and is outdated.
-      def compute_sized_formulae(formulae, args:)
-        sized_formulae = formulae.flat_map do |formula|
-          # Always include the formula itself.
-          formula_list = [formula]
-
-          deps = args.build_from_source? ? formula.deps.build : formula.deps.required
-
-          outdated_dependents = deps.map(&:to_formula).reject(&:pinned?).select do |dep|
-            dep.installed_kegs.empty? || (dep.bottled? && dep.outdated?)
-          end
-          deps.map(&:to_formula).each do |f|
-            outdated_dependents.concat(f.recursive_dependencies.map(&:to_formula).reject(&:pinned?).select do |dep|
-              dep.installed_kegs.empty? || (dep.bottled? && dep.outdated?)
-            end)
-          end
-          formula_list.concat(outdated_dependents)
-
-          formula_list
-        end
-
-        # Add any installed formula that depends on one of the sized formulae and is outdated.
-        unless Homebrew::EnvConfig.no_installed_dependents_check?
-          sized_formulae.concat(Formula.installed.select do |installed_formula|
-            installed_formula.bottled? && installed_formula.outdated? &&
-              installed_formula.deps.required.map(&:to_formula).intersect?(sized_formulae)
-          end)
-        end
-
-        sized_formulae.uniq(&:to_s).compact
-      end
-
       # Compute the total sizes (download, installed, and net) for the given formulae.
       def compute_total_sizes(sized_formulae, debug: false)
         total_download_size  = 0
@@ -471,6 +461,16 @@ module Homebrew
           installed: total_installed_size,
           net:       total_net_size }
       end
+
+      def collect_dependencies(formulae_installer, dependants)
+        formulae_dependencies = formulae_installer.flat_map do |f|
+          [f.formula, f.compute_dependencies.flatten.filter do |c|
+            c.is_a? Dependency
+          end.flat_map(&:to_formula)]
+        end.flatten.uniq
+        formulae_dependencies.concat(dependants.upgradeable) if dependants&.upgradeable
+        formulae_dependencies
+      end
     end
   end
 end
diff --git a/Library/Homebrew/reinstall.rb b/Library/Homebrew/reinstall.rb
index b8260b1116..4d5ff2485c 100644
--- a/Library/Homebrew/reinstall.rb
+++ b/Library/Homebrew/reinstall.rb
@@ -7,7 +7,9 @@ require "messages"
 
 module Homebrew
   module Reinstall
-    def self.reinstall_formula(
+    # struct to keep context of the current installer, keg, formula and option
+    InstallationContext = Struct.new(:formula_installer, :keg, :formula, :options)
+    def self.build_install_context(
       formula,
       flags:,
       force_bottle: false,
@@ -61,16 +63,38 @@ module Homebrew
           verbose:,
         }.compact,
       )
-      fi.prelude
-      fi.fetch
+      InstallationContext.new(fi, keg, formula, options)
+    end
+
+    def self.reinstall_formula(
+      install_context,
+      flags:,
+      force_bottle: false,
+      build_from_source_formulae: [],
+      interactive: false,
+      keep_tmp: false,
+      debug_symbols: false,
+      force: false,
+      debug: false,
+      quiet: false,
+      verbose: false,
+      git: false
+    )
+      formula_installer = install_context.formula_installer
+      keg = install_context.keg
+      formula = install_context.formula
+      options = install_context.options
+      link_keg = keg.linked?
+      formula_installer.prelude
+      formula_installer.fetch
 
       oh1 "Reinstalling #{Formatter.identifier(formula.full_name)} #{options.to_a.join " "}"
 
-      fi.install
-      fi.finish
+      formula_installer.install
+      formula_installer.finish
     rescue FormulaInstallationAlreadyAttemptedError
       nil
-    # Any other exceptions we want to restore the previous keg and report the error.
+      # Any other exceptions we want to restore the previous keg and report the error.
     rescue Exception # rubocop:disable Lint/RescueException
       ignore_interrupts { restore_backup(keg, link_keg, verbose:) }
       raise
diff --git a/Library/Homebrew/test/cmd/install_spec.rb b/Library/Homebrew/test/cmd/install_spec.rb
index ef74f06cc3..1e8d70948d 100644
--- a/Library/Homebrew/test/cmd/install_spec.rb
+++ b/Library/Homebrew/test/cmd/install_spec.rb
@@ -95,34 +95,4 @@ RSpec.describe Homebrew::Cmd::InstallCmd do
 
     expect(HOMEBREW_CELLAR/"testball1/0.1/bin/test").to be_a_file
   end
-
-  it "installs with asking for user prompts with installed dependent checks", :integration_test do
-    setup_test_formula "testball1", <<~RUBY
-      depends_on "testball5"
-      # should work as its not building but test doesnt pass if dependant
-      # depends_on "build" => :build
-      depends_on "installed"
-    RUBY
-    setup_test_formula "installed"
-    setup_test_formula "testball5", <<~RUBY
-      depends_on "testball4"
-    RUBY
-    setup_test_formula "testball4", ""
-    setup_test_formula "hiop"
-    setup_test_formula "build"
-
-    # Mock `Formula#any_version_installed?` by creating the tab in a plausible keg directory
-    keg_dir = HOMEBREW_CELLAR/"installed"/"1.0"
-    keg_dir.mkpath
-    touch keg_dir/AbstractTab::FILENAME
-
-    expect do
-      brew "install", "--ask", "testball1"
-    end.to output(/.*Formulae\s*\(3\):\s*testball1\s*,?\s*testball5\s*,?\s*testball4.*/).to_stdout
-                                                                                        .and not_to_output.to_stderr
-
-    expect(HOMEBREW_CELLAR/"testball1/0.1/bin/test").to be_a_file
-    expect(HOMEBREW_CELLAR/"testball4/0.1/bin/testball4").to be_a_file
-    expect(HOMEBREW_CELLAR/"testball5/0.1/bin/testball5").to be_a_file
-  end
 end
diff --git a/Library/Homebrew/test/cmd/upgrade_spec.rb b/Library/Homebrew/test/cmd/upgrade_spec.rb
index 59918aaf02..cc82c242c4 100644
--- a/Library/Homebrew/test/cmd/upgrade_spec.rb
+++ b/Library/Homebrew/test/cmd/upgrade_spec.rb
@@ -28,48 +28,4 @@ RSpec.describe Homebrew::Cmd::UpgradeCmd do
     expect(HOMEBREW_CELLAR/"testball/0.1").to be_a_directory
     expect(HOMEBREW_CELLAR/"testball/0.0.1").not_to exist
   end
-
-  it "upgrades with asking for user prompts with dependants checks", :integration_test do
-    setup_test_formula "testball", <<~RUBY
-      depends_on "testball5"
-      # should work as its not building but test doesnt pass if dependant
-      # depends_on "build" => :build
-      depends_on "installed"
-    RUBY
-    setup_test_formula "installed"
-    setup_test_formula "testball5", <<~RUBY
-      depends_on "testball4"
-    RUBY
-    setup_test_formula "testball4"
-    setup_test_formula "hiop"
-    setup_test_formula "build"
-
-    (HOMEBREW_CELLAR/"testball/0.0.1/foo").mkpath
-    (HOMEBREW_CELLAR/"testball5/0.0.1/foo").mkpath
-    (HOMEBREW_CELLAR/"testball4/0.0.1/foo").mkpath
-
-    keg_dir = HOMEBREW_CELLAR/"installed"/"1.0"
-    keg_dir.mkpath
-    touch keg_dir/AbstractTab::FILENAME
-
-    regex = /
-      Formulae\s*\(3\):\s*
-      (testball|testball5|testball4)
-      \s*,\s*
-      ((?!\1)testball|testball5|testball4)
-      \s*,\s*
-      ((?!\1|\2)testball|testball5|testball4)
-    /x
-    expect do
-      brew "upgrade", "--ask"
-    end.to output(regex)
-      .to_stdout.and not_to_output.to_stderr
-
-    expect(HOMEBREW_CELLAR/"testball/0.1").to be_a_directory
-    expect(HOMEBREW_CELLAR/"testball/0.0.1").not_to exist
-    expect(HOMEBREW_CELLAR/"testball5/0.1").to be_a_directory
-    expect(HOMEBREW_CELLAR/"testball5/0.0.1").not_to exist
-    expect(HOMEBREW_CELLAR/"testball4/0.1").to be_a_directory
-    expect(HOMEBREW_CELLAR/"testball4/0.0.1").not_to exist
-  end
 end
diff --git a/Library/Homebrew/test/support/fixtures/tarballs/testball4-0.1-linux.tbz b/Library/Homebrew/test/support/fixtures/tarballs/testball4-0.1-linux.tbz
deleted file mode 100644
index 72957a4c13..0000000000
Binary files a/Library/Homebrew/test/support/fixtures/tarballs/testball4-0.1-linux.tbz and /dev/null differ
diff --git a/Library/Homebrew/test/support/fixtures/tarballs/testball4-0.1.tbz b/Library/Homebrew/test/support/fixtures/tarballs/testball4-0.1.tbz
deleted file mode 100644
index c7c57aee5f..0000000000
Binary files a/Library/Homebrew/test/support/fixtures/tarballs/testball4-0.1.tbz and /dev/null differ
diff --git a/Library/Homebrew/test/support/fixtures/tarballs/testball5-0.1-linux.tbz b/Library/Homebrew/test/support/fixtures/tarballs/testball5-0.1-linux.tbz
deleted file mode 100644
index 4d35e20d2b..0000000000
Binary files a/Library/Homebrew/test/support/fixtures/tarballs/testball5-0.1-linux.tbz and /dev/null differ
diff --git a/Library/Homebrew/test/support/fixtures/tarballs/testball5-0.1.tbz b/Library/Homebrew/test/support/fixtures/tarballs/testball5-0.1.tbz
deleted file mode 100644
index 06def51fbd..0000000000
Binary files a/Library/Homebrew/test/support/fixtures/tarballs/testball5-0.1.tbz and /dev/null differ
diff --git a/Library/Homebrew/test/support/helper/spec/shared_context/integration_test.rb b/Library/Homebrew/test/support/helper/spec/shared_context/integration_test.rb
index e402974813..6c24f3635e 100644
--- a/Library/Homebrew/test/support/helper/spec/shared_context/integration_test.rb
+++ b/Library/Homebrew/test/support/helper/spec/shared_context/integration_test.rb
@@ -135,21 +135,13 @@ RSpec.shared_context "integration test" do # rubocop:disable RSpec/ContextWordin
                          bottle_block: nil, tab_attributes: nil)
     case name
     when /^testball/
-      case name
-      when "testball4", "testball5"
-        prefix = name
-        program_name = name
-      when "testball2"
-        prefix = name
-        program_name = "test"
+      # Use a different tarball for testball2 to avoid lock errors when writing concurrency tests
+      prefix = (name == "testball2") ? "testball2" : "testball"
+      tarball = if OS.linux?
+        TEST_FIXTURE_DIR/"tarballs/#{prefix}-0.1-linux.tbz"
       else
-        prefix = "testball"
-        program_name = "test"
+        TEST_FIXTURE_DIR/"tarballs/#{prefix}-0.1.tbz"
       end
-
-      tarball_name = "#{prefix}-0.1#{"-linux" if OS.linux?}.tbz"
-      tarball = TEST_FIXTURE_DIR / "tarballs/#{tarball_name}"
-
       content = <<~RUBY
         desc "Some test"
         homepage "https://brew.sh/#{name}"
@@ -159,12 +151,12 @@ RSpec.shared_context "integration test" do # rubocop:disable RSpec/ContextWordin
         option "with-foo", "Build with foo"
         #{bottle_block}
         def install
-          (prefix/"foo"/"#{program_name}").write("#{program_name}") if build.with? "foo"
+          (prefix/"foo"/"test").write("test") if build.with? "foo"
           prefix.install Dir["*"]
-          (buildpath/"#{program_name}.c").write \
-            "#include <stdio.h>\\nint main(){printf(\\"#{program_name}\\");return 0;}"
+          (buildpath/"test.c").write \
+            "#include <stdio.h>\\nint main(){printf(\\"test\\");return 0;}"
           bin.mkpath
-          system ENV.cc, "#{program_name}.c", "-o", bin/"#{program_name}"
+          system ENV.cc, "test.c", "-o", bin/"test"
         end
 
         #{content}
diff --git a/Library/Homebrew/upgrade.rb b/Library/Homebrew/upgrade.rb
index 112893aac1..fa7bcf7c1f 100644
--- a/Library/Homebrew/upgrade.rb
+++ b/Library/Homebrew/upgrade.rb
@@ -11,7 +11,9 @@ require "utils/topological_hash"
 module Homebrew
   # Helper functions for upgrading formulae.
   module Upgrade
-    def self.upgrade_formulae(
+    Dependents = Struct.new(:upgradeable, :pinned, :skipped)
+
+    def self.formula_installers(
       formulae_to_install,
       flags:,
       dry_run: false,
@@ -48,7 +50,7 @@ module Homebrew
         raise CyclicDependencyError, dependency_graph.strongly_connected_components if Homebrew::EnvConfig.developer?
       end
 
-      formula_installers = formulae_to_install.filter_map do |formula|
+      formulae_to_install.filter_map do |formula|
         Migrator.migrate_if_needed(formula, force:, dry_run:)
         begin
           fi = create_formula_installer(
@@ -65,18 +67,19 @@ module Homebrew
             quiet:,
             verbose:,
           )
-          unless dry_run
-            fi.prelude
+          fi.fetch_bottle_tab(quiet: !debug)
 
+          all_runtime_deps_installed = fi.bottle_tab_runtime_dependencies.presence&.all? do |dependency, hash|
+            minimum_version = Version.new(hash["version"]) if hash["version"].present?
+            Dependency.new(dependency).installed?(minimum_version:, minimum_revision: hash["revision"])
+          end
+
+          if !dry_run && dependents && all_runtime_deps_installed
             # Don't need to install this bottle if all of the runtime
             # dependencies have the same or newer version already installed.
-            next if dependents && fi.bottle_tab_runtime_dependencies.presence&.all? do |dependency, hash|
-              minimum_version = Version.new(hash["version"]) if hash["version"].present?
-              Dependency.new(dependency).installed?(minimum_version:, minimum_revision: hash["revision"])
-            end
-
-            fi.fetch
+            next
           end
+
           fi
         rescue CannotInstallFormulaError => e
           ofail e
@@ -86,6 +89,19 @@ module Homebrew
           nil
         end
       end
+    end
+
+    def self.upgrade_formulae(formula_installers, dry_run: false, verbose: false)
+      unless dry_run
+        formula_installers.each do |fi|
+          fi.prelude
+          fi.fetch
+        rescue CannotInstallFormulaError => e
+          ofail e
+        rescue UnsatisfiedRequirements, DownloadError => e
+          ofail "#{fi.formula.full_name}: #{e}"
+        end
+      end
 
       formula_installers.each do |fi|
         upgrade_formula(fi, dry_run:, verbose:)
@@ -250,10 +266,11 @@ module Homebrew
       @puts_no_installed_dependents_check_disable_message_if_not_already = true
     end
 
-    def self.check_installed_dependents(
+    def self.dependants(
       formulae,
       flags:,
       dry_run: false,
+      ask: false,
       installed_on_request: false,
       force_bottle: false,
       build_from_source_formulae: [],
@@ -274,35 +291,26 @@ module Homebrew
         end
         return
       end
+      formulae_to_install = formulae.dup
+      formulae_to_install.reject! { |f| f.core_formula? && f.versioned_formula? }
+      return if formulae_to_install.empty?
 
-      installed_formulae = (dry_run ? formulae : FormulaInstaller.installed.to_a).dup
-      installed_formulae.reject! { |f| f.core_formula? && f.versioned_formula? }
-      return if installed_formulae.empty?
-
-      already_broken_dependents = check_broken_dependents(installed_formulae)
+      already_broken_dependents = check_broken_dependents(formulae_to_install)
 
       # TODO: this should be refactored to use FormulaInstaller new logic
       outdated_dependents =
-        installed_formulae.flat_map(&:runtime_installed_formula_dependents)
-                          .uniq
-                          .select(&:outdated?)
+        formulae_to_install.flat_map(&:runtime_installed_formula_dependents)
+                           .uniq
+                           .select(&:outdated?)
 
       # Ensure we never attempt a source build for outdated dependents of upgraded formulae.
       outdated_dependents, skipped_dependents = outdated_dependents.partition do |dependent|
         dependent.bottled? && dependent.deps.map(&:to_formula).all?(&:bottled?)
       end
 
-      if skipped_dependents.present?
-        opoo <<~EOS
-          The following dependents of upgraded formulae are outdated but will not
-          be upgraded because they are not bottled:
-            #{skipped_dependents * "\n  "}
-        EOS
-      end
-
       return if outdated_dependents.blank? && already_broken_dependents.blank?
 
-      outdated_dependents -= installed_formulae if dry_run
+      outdated_dependents -= formulae_to_install if dry_run
 
       upgradeable_dependents =
         outdated_dependents.reject(&:pinned?)
@@ -311,24 +319,52 @@ module Homebrew
         outdated_dependents.select(&:pinned?)
                            .sort { |a, b| depends_on(a, b) }
 
-      if pinned_dependents.present?
-        plural = Utils.pluralize("dependent", pinned_dependents.count)
-        opoo "Not upgrading #{pinned_dependents.count} pinned #{plural}:"
-        puts(pinned_dependents.map do |f|
+      Dependents.new(upgradeable_dependents, pinned_dependents, skipped_dependents)
+    end
+
+    def self.upgrade_dependents(deps, formulae,
+                                flags:,
+                                dry_run: false,
+                                installed_on_request: false,
+                                force_bottle: false,
+                                build_from_source_formulae: [],
+                                interactive: false,
+                                keep_tmp: false,
+                                debug_symbols: false,
+                                force: false,
+                                debug: false,
+                                quiet: false,
+                                verbose: false)
+      return if deps.blank?
+
+      upgradeable = deps.upgradeable
+      pinned      = deps.pinned
+      skipped     = deps.skipped
+      if pinned.present?
+        plural = Utils.pluralize("dependent", pinned.count)
+        opoo "Not upgrading #{pinned.count} pinned #{plural}:"
+        puts(pinned.map do |f|
           "#{f.full_specified_name} #{f.pkg_version}"
         end.join(", "))
       end
-
+      if skipped.present?
+        opoo <<~EOS
+          The following dependents of upgraded formulae are outdated but will not
+          be upgraded because they are not bottled:
+            #{skipped * "\n  "}
+        EOS
+      end
       # Print the upgradable dependents.
-      if upgradeable_dependents.blank?
+      if upgradeable.blank?
         ohai "No outdated dependents to upgrade!" unless dry_run
       else
+        installed_formulae = (dry_run ? formulae : FormulaInstaller.installed.to_a).dup
         formula_plural = Utils.pluralize("formula", installed_formulae.count, plural: "e")
         upgrade_verb = dry_run ? "Would upgrade" : "Upgrading"
-        ohai "#{upgrade_verb} #{Utils.pluralize("dependent", upgradeable_dependents.count,
+        ohai "#{upgrade_verb} #{Utils.pluralize("dependent", upgradeable.count,
                                                 include_count: true)} of upgraded #{formula_plural}:"
         Upgrade.puts_no_installed_dependents_check_disable_message_if_not_already!
-        formulae_upgrades = upgradeable_dependents.map do |f|
+        formulae_upgrades = upgradeable.map do |f|
           name = f.full_specified_name
           if f.optlinked?
             "#{name} #{Keg.new(f.opt_prefix).version} -> #{f.pkg_version}"
@@ -340,8 +376,8 @@ module Homebrew
       end
 
       unless dry_run
-        upgrade_formulae(
-          upgradeable_dependents,
+        dependent_installers = formula_installers(
+          upgradeable,
           flags:,
           force_bottle:,
           build_from_source_formulae:,
@@ -354,6 +390,9 @@ module Homebrew
           quiet:,
           verbose:,
         )
+        puts "here", dependent_installers
+        puts "here", upgradeable
+        upgrade_formulae(dependent_installers, dry_run: dry_run, verbose: verbose)
       end
 
       # Update installed formulae after upgrading
@@ -409,7 +448,7 @@ module Homebrew
       return if dry_run
 
       reinstallable_broken_dependents.each do |formula|
-        Reinstall.reinstall_formula(
+        formula_installer = Reinstall.build_install_context(
           formula,
           flags:,
           force_bottle:,
@@ -422,6 +461,19 @@ module Homebrew
           quiet:,
           verbose:,
         )
+        Reinstall.reinstall_formula(
+          formula_installer,
+          flags:,
+          force_bottle:,
+          build_from_source_formulae:,
+          interactive:,
+          keep_tmp:,
+          debug_symbols:,
+          force:,
+          debug:,
+          quiet:,
+          verbose:,
+        )
       rescue FormulaInstallationAlreadyAttemptedError
         # We already attempted to reinstall f as part of the dependency tree of
         # another formula. In that case, don't generate an error, just move on.