text = 'am pm P.M. 10:56pm 10:43 a.m.'
rx = /\b((?:[01]?[0-9]|[2][0-3]):[0-5][0-9]\s*[pa]\.?m\b\.?)|\b[ap]\.?m\b\.?/i
result = text.gsub(rx) { $1 || "\n" }
p result
dGV4dCA9ICdhbSBwbSAgUC5NLiAgMTA6NTZwbSAxMDo0MyBhLm0uJwpyeCA9IC9cYigoPzpbMDFdP1swLTldfFsyXVswLTNdKTpbMC01XVswLTldXHMqW3BhXVwuP21cYlwuPyl8XGJbYXBdXC4/bVxiXC4/L2kKcmVzdWx0ID0gdGV4dC5nc3ViKHJ4KSB7ICQxIHx8ICJcbiIgfQpwIHJlc3VsdA==