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let str = "###Word1 Word2\nWord3\nWord4 Word5 Word6\n##Word7\n#Word8 Word9\n"; str = str.replace(/#+(.*)\n/g, "_$1_\n"); console.log(str); /* run: _Word1 Word2_ Word3 Word4 Word5 Word6 _Word7_ _Word8 Word9_ */