diff --git a/Library/Homebrew/install.rb b/Library/Homebrew/install.rb
index 8fba7fabf7..eed1d65f18 100644
--- a/Library/Homebrew/install.rb
+++ b/Library/Homebrew/install.rb
@@ -428,7 +428,11 @@ module Homebrew
             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outdated?)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|
+            prune_build = f.recursive_dependencies do |_, dep|
+              :prune if dep.build?
+            end
+            # select the outdated one or not installed
+            outdated_dependents.concat(prune_build.map(&:to_formula).reject(&:pinned?).select do |dep|
               dep.installed_kegs.empty? || (dep.bottled? && dep.outdated?)
             end)
           end
@@ -436,13 +440,23 @@ module Homebrew
 
           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         # Add any installed formula that depends on one of the sized formulae and is outdated.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outdated?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)
+          loop do
+            new_parents = Formula.installed.select do |installed_formula|
+              next unless installed_formula.bottled?
+              next unless installed_formula.outdated?
+
+              required_deps = installed_formula.deps.required.map(&:to_formula)
+              required_deps.intersect?(sized_formulae)
+            end
+
+            # Exclude anything already in sized_formulae
+            new_parents -= sized_formulae
+            break if new_parents.empty?
+
+            sized_formulae.concat(new_parents)
+          end
         end
 
         sized_formulae.uniq(&:to_s).compact