gistfile1.txt

var expect, fs;
expect = require('chai').expect;
fs = require('fs');

// list all files in scripts
// check each script for a Category comment
// fail if it's missing
describe('category', function() {
  var bool, f, re, results, text;
  re = /[\#|\/\/]\s+category[:?]\s+(workflow|social)/i;
  results = [];
  fs.readdirSync('tt').forEach(function(f) {
    describe("All scripts should have a category", function() {
      it("Should have a known category for " + f, function(done) {
        text = fs.readFileSync('./tt/' + f).toString();
        bool = re.test(text);
        results.push(expect(bool).to.eql(true));
        done();
      })
      return results;
    });
  });
})

test.coffee

#/usr/bin/env coffee
Helper = require('hubot-test-helper')
expect = require('chai').expect
fs = require 'fs'

# Objective
# list all files in scripts
# check each script for a Category comment
# fail if it's missing

describe 'category', ->
  context "All scripts should have a category", ->
    files = fs.readdirSync('tt');
    re = /category/i
    for f in files
      it "ensures a category exists for #{f}", -> 
        text = fs.readFileSync('./tt/' + f).toString(); # f is always the same value here, because non-blocking IO is dumb (or I am)
        console.log(text)
        bool = re.test(text)
        expect(bool).to.eql(true)

describe 'category', ->
  context "All scripts should have a category", ->
    it "ensures a category exists for files", -> 
      files = fs.readdirSync('tt');
      re = /category/i
      for f in files
        text = fs.readFileSync('./tt/' + f).toString(); # f is always the same value here, because non-blocking IO is dumb (or I am)
        console.log(text)
        bool = re.test(text)
        expect(bool).to.eql(true, "File #{f} has a category")

Drawback: It will fail on first file that doesn't have a category
Positive: It works.