diff --git a/Library/Homebrew/cmd/reinstall.rb b/Library/Homebrew/cmd/reinstall.rb
index bacf33beaac90..6c660560076d3 100644
--- a/Library/Homebrew/cmd/reinstall.rb
+++ b/Library/Homebrew/cmd/reinstall.rb
@@ -138,7 +138,6 @@ def run
             Homebrew::Reinstall.reinstall_formula(
               formula,
               flags:                      args.flags_only,
-              installed_on_request:       args.named.present?,
               force_bottle:               args.force_bottle?,
               build_from_source_formulae: args.build_from_source_formulae,
               interactive:                args.interactive?,
@@ -156,7 +155,6 @@ def run
           Upgrade.check_installed_dependents(
             formulae,
             flags:                      args.flags_only,
-            installed_on_request:       args.named.present?,
             force_bottle:               args.force_bottle?,
             build_from_source_formulae: args.build_from_source_formulae,
             interactive:                args.interactive?,
diff --git a/Library/Homebrew/cmd/upgrade.rb b/Library/Homebrew/cmd/upgrade.rb
index cf17914f10d53..5511cd71e0d4d 100644
--- a/Library/Homebrew/cmd/upgrade.rb
+++ b/Library/Homebrew/cmd/upgrade.rb
@@ -220,7 +220,6 @@ def upgrade_outdated_formulae(formulae)
           formulae_to_install,
           flags:                      args.flags_only,
           dry_run:                    args.dry_run?,
-          installed_on_request:       args.named.present?,
           force_bottle:               args.force_bottle?,
           build_from_source_formulae: args.build_from_source_formulae,
           interactive:                args.interactive?,
@@ -237,7 +236,6 @@ def upgrade_outdated_formulae(formulae)
           formulae_to_install,
           flags:                      args.flags_only,
           dry_run:                    args.dry_run?,
-          installed_on_request:       args.named.present?,
           force_bottle:               args.force_bottle?,
           build_from_source_formulae: args.build_from_source_formulae,
           interactive:                args.interactive?,
diff --git a/Library/Homebrew/formula_installer.rb b/Library/Homebrew/formula_installer.rb
index c26e12b424013..e28e83d0bd94c 100644
--- a/Library/Homebrew/formula_installer.rb
+++ b/Library/Homebrew/formula_installer.rb
@@ -84,7 +84,7 @@ def initialize(
     formula,
     link_keg: false,
     installed_as_dependency: false,
-    installed_on_request: true,
+    installed_on_request: false,
     show_header: false,
     build_bottle: false,
     skip_post_install: false,
diff --git a/Library/Homebrew/install.rb b/Library/Homebrew/install.rb
index bf03c18c070fb..aea4eba02e88d 100644
--- a/Library/Homebrew/install.rb
+++ b/Library/Homebrew/install.rb
@@ -259,6 +259,8 @@ def install_formulae(
           formula_installer = FormulaInstaller.new(
             formula,
             options:                    build_options.used_options,
+            installed_on_request:       true,
+            installed_as_dependency:    false,
             build_bottle:,
             force_bottle:,
             bottle_arch:,
diff --git a/Library/Homebrew/reinstall.rb b/Library/Homebrew/reinstall.rb
index 6e5ba2613144e..25e27bcc141a8 100644
--- a/Library/Homebrew/reinstall.rb
+++ b/Library/Homebrew/reinstall.rb
@@ -10,7 +10,6 @@ module Reinstall
     def self.reinstall_formula(
       formula,
       flags:,
-      installed_on_request: false,
       force_bottle: false,
       build_from_source_formulae: [],
       interactive: false,
@@ -25,9 +24,16 @@ def self.reinstall_formula(
       if formula.opt_prefix.directory?
         keg = Keg.new(formula.opt_prefix.resolved_path)
         tab = keg.tab
-        keg_had_linked_opt = true
-        keg_was_linked = keg.linked?
+        link_keg = keg.linked?
+        installed_as_dependency = tab.installed_as_dependency
+        installed_on_request = tab.installed_on_request
+        build_bottle = tab.built_bottle?
         backup keg
+      else
+        link_keg = nil
+        installed_as_dependency = false
+        installed_on_request = true
+        build_bottle = false
       end
 
       build_options = BuildOptions.new(Options.create(flags), formula.options)
@@ -39,10 +45,10 @@ def self.reinstall_formula(
         formula,
         **{
           options:,
-          link_keg:                   keg_had_linked_opt ? keg_was_linked : nil,
-          installed_as_dependency:    tab&.installed_as_dependency,
-          installed_on_request:       installed_on_request || tab&.installed_on_request,
-          build_bottle:               tab&.built_bottle?,
+          link_keg:,
+          installed_as_dependency:,
+          installed_on_request:,
+          build_bottle:,
           force_bottle:,
           build_from_source_formulae:,
           git:,
@@ -65,7 +71,7 @@ def self.reinstall_formula(
     rescue FormulaInstallationAlreadyAttemptedError
       nil
     rescue Exception # rubocop:disable Lint/RescueException
-      ignore_interrupts { restore_backup(keg, keg_was_linked, verbose:) }
+      ignore_interrupts { restore_backup(keg, link_keg, verbose:) }
       raise
     else
       begin
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 21d23905f87af..9981aabadad59 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
@@ -202,7 +202,7 @@ class #{Formulary.class_s(name)} < Formula
 
   def install_test_formula(name, content = nil, build_bottle: false)
     setup_test_formula(name, content)
-    fi = FormulaInstaller.new(Formula[name], build_bottle:)
+    fi = FormulaInstaller.new(Formula[name], build_bottle:, installed_on_request: true)
     fi.prelude
     fi.fetch
     fi.install
diff --git a/Library/Homebrew/upgrade.rb b/Library/Homebrew/upgrade.rb
index 8fa8df49adfaa..0ddb973bcf9b6 100644
--- a/Library/Homebrew/upgrade.rb
+++ b/Library/Homebrew/upgrade.rb
@@ -15,7 +15,6 @@ def self.upgrade_formulae(
       formulae_to_install,
       flags:,
       dry_run: false,
-      installed_on_request: false,
       force_bottle: false,
       build_from_source_formulae: [],
       dependents: false,
@@ -55,7 +54,6 @@ def self.upgrade_formulae(
           fi = create_formula_installer(
             formula,
             flags:,
-            installed_on_request:,
             force_bottle:,
             build_from_source_formulae:,
             interactive:,
@@ -114,7 +112,6 @@ def self.upgrade_formulae(
     private_class_method def self.create_formula_installer(
       formula,
       flags:,
-      installed_on_request: false,
       force_bottle: false,
       build_from_source_formulae: [],
       interactive: false,
@@ -126,15 +123,24 @@ def self.upgrade_formulae(
       quiet: false,
       verbose: false
     )
-      if formula.opt_prefix.directory?
-        keg = Keg.new(formula.opt_prefix.resolved_path)
-        keg_had_linked_opt = true
-        keg_was_linked = keg.linked?
+      keg = if formula.optlinked?
+        Keg.new(formula.opt_prefix.resolved_path)
+      else
+        formula.installed_kegs.find(&:optlinked?)
       end
 
-      if formula.opt_prefix.directory?
+      if keg
         keg = Keg.new(formula.opt_prefix.resolved_path)
         tab = keg.tab
+        link_keg = keg.linked?
+        installed_as_dependency = tab.installed_as_dependency
+        installed_on_request = tab.installed_on_request
+        build_bottle = tab.built_bottle?
+      else
+        link_keg = nil
+        installed_as_dependency = false
+        installed_on_request = true
+        build_bottle = false
       end
 
       build_options = BuildOptions.new(Options.create(flags), formula.options)
@@ -146,10 +152,10 @@ def self.upgrade_formulae(
         formula,
         **{
           options:,
-          link_keg:                   keg_had_linked_opt ? keg_was_linked : nil,
-          installed_as_dependency:    tab&.installed_as_dependency,
-          installed_on_request:       installed_on_request || tab&.installed_on_request,
-          build_bottle:               tab&.built_bottle?,
+          link_keg:,
+          installed_as_dependency:,
+          installed_on_request:,
+          build_bottle:,
           force_bottle:,
           build_from_source_formulae:,
           interactive:,
@@ -338,7 +344,6 @@ def self.check_installed_dependents(
         upgrade_formulae(
           upgradeable_dependents,
           flags:,
-          installed_on_request:,
           force_bottle:,
           build_from_source_formulae:,
           dependents:                 true,