The regex gurus on this forum might come up with some kind of crazy regex-based solution to this, but this is pretty easy to solve with PythonScript.
# requires PythonScript: https://github.com/bruderstein/PythonScript/releases # ref: https://community.notepad-plus-plus.org/topic/25388/replace-guid-with-guid-from-list-randomly import random import re from Npp import editor, notepad, MESSAGEBOXFLAGS def main(): thing_to_replace = notepad.prompt('Enter the text you want to replace', 'enter text to replace', '') if not thing_to_replace: return is_regex = notepad.messageBox( 'Is the thing you want to replace a regular expression?', 'regular expression?', MESSAGEBOXFLAGS.YESNO) == MESSAGEBOXFLAGS.RESULTYES if not is_regex: thing_to_replace = '(?-s)' + re.escape(thing_to_replace) replacements = notepad.prompt( 'Enter a list of replacements (one per line)', 'list of replacements', '') if not replacements: return replacement_list = replacements.strip().splitlines() def get_random_from_list(_): return random.choice(replacement_list) editor.rereplace(thing_to_replace, get_random_from_list) if __name__ == '__main__': main()