diff --git a/Library/Homebrew/cmd/install.rb b/Library/Homebrew/cmd/install.rb
index 517414f9fe..79e6b527ac 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.get_formulae_dependencies(
           installed_formulae,
           installed_on_request:       !args.as_dependency?,
           installed_as_dependency:    args.as_dependency?,
@@ -338,21 +336,71 @@ module Homebrew
           skip_link:                  args.skip_link?,
         )
 
-        Upgrade.check_installed_dependents(
-          installed_formulae,
-          flags:                      args.flags_only,
-          installed_on_request:       !args.as_dependency?,
-          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?,
-          dry_run:                    args.dry_run?,
-        )
+        if args.ask?
+          dependants = Upgrade.get_dependants(
+            installed_formulae,
+            flags:                      args.flags_only,
+            installed_on_request:       !args.as_dependency?,
+            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?,
+            dry_run:                    args.dry_run?,
+          )
+
+          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
+          # Main block: if asking the user is enabled, show dependency and size information.
+          Install.ask_formulae(formulae_dependencies, args: args)
+        end
+
+        Upgrade.upgrade_formulae(formulae_installer,
+                                 dry_run: args.dry_run?,
+                                 verbose: args.verbose?)
+
+        unless args.ask?
+          dependants = Upgrade.get_dependants(
+            installed_formulae,
+            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?,
+          )
+        end
+
+        if dependants
+          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?
+          )
+        end
 
         Cleanup.periodic_clean!(dry_run: args.dry_run?)
 
diff --git a/Library/Homebrew/install.rb b/Library/Homebrew/install.rb
index 561c27e601..bcf328c46d 100644
--- a/Library/Homebrew/install.rb
+++ b/Library/Homebrew/install.rb
@@ -232,7 +232,7 @@ module Homebrew
         false
       end
 
-      def install_formulae(
+      def get_formulae_dependencies(
         formulae_to_install,
         installed_on_request: true,
         installed_as_dependency: false,
@@ -257,11 +257,11 @@ 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:,
@@ -286,24 +286,36 @@ 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(" ")
@@ -316,6 +328,18 @@ 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