diff --git a/Library/Homebrew/cleanup.rb b/Library/Homebrew/cleanup.rb
index d89ecf20d7570038939c79f82ff922c3d1a29812..0252ba785b8f14d13a69224030056269f5ca86aa 100644
--- a/Library/Homebrew/cleanup.rb
+++ b/Library/Homebrew/cleanup.rb
@@ -43,6 +43,8 @@ module CleanupRefinement
       return false unless days
       return true if days.zero?
 
+      return true if symlink? && !exist?
+
       # TODO: Replace with ActiveSupport's `.days.ago`.
       mtime < ((@time ||= Time.now) - days * 60 * 60 * 24)
     end