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 foreach $ip(@ip) {
   print $out "#" if(/\b$ip\b/i && !/^#/); #only one # at front of lin
+e
   print $out $_;
 }

 foreach $ip(@ip) {
   last if /^#/; # ALready has a hash . Note - LAST exists this loop
...
   last; # Remember to exit loop after one successful match
 }
print $_; # Print onloy once.