@M-Andre-Z-Eckenrode I may not fully understand the regex task with using groups when ' can be at the start of a line with a word character following as to \W can match the preceding LineFeed character. The LineFeed character seems unwise to capture in my opinion. \W can change behavior depending on encoding so might be challenging to use so perhaps if can be avoided, then that might be better. The find pattern of \B'\b and replace with ’ might be safer to use as to using anchors to qualify the match instead of consuming with groups which may need more complex conditional handling.