const regex = /([^#\n]+\n#[\w ]+?\n[^\n]+(?:\n|$))|^([^\n]+\n)/gm;
// Alternative syntax using RegExp constructor
// const regex = new RegExp('([^#\\n]+\\n#[\\w ]+?\\n[^\\n]+(?:\\n|$))|^([^\\n]+\\n)', 'gm')
const str = `The quick
#a comment
brown
fox jumps
#another comment
over
the
lazy
#yet another comment
dog`;
const subst = `#auto comment\n$1$2`;
// The substituted value will be contained in the result variable
const result = str.replace(regex, subst);
console.log('Substitution result: ', result);
Please keep in mind that these code samples are automatically generated and are not guaranteed to work. If you find any syntax errors, feel free to submit a bug report. For a full regex reference for JavaScript, please visit: https://developer.mozilla.org/en/docs/Web/JavaScript/Guide/Regular_Expressions