Personally, I don't like having to perform the same test ($tries == $max_tries) twice.

my $max_tries = 5;

foreach $item (@array) {
   my $tries = 0;
   while (!some_test($item)) {
      die "Failed $tries times, aborting"
         if ++$tries == $max_tries;
      print "Failure: $item, trying again after sleep\n";
      sleep 10;
   }

   print "Success: $item\n";
}
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