Win8 Strawberry 5.30.3.1 (64) Tue 09/06/2022 17:27:14 C:\@Work\Perl\monks >perl use 5.010; # need \K regex extension use strict; use warnings; use autodie; use Data::Dump qw(dd); # for debug my $file_paths = <<'EOFILEPATHS'; # known file paths /unix/path/to/folder/is/here /unix/path/to/folder/also /unix/path/to/another/folder EOFILEPATHS open my $fh_reference_paths, '<', \$file_paths; my ($rx_reference) = map qr{ $_ }xms, join ' | ', map quotemeta, reverse sort map { chomp; $_; } <$fh_reference_paths> ; # dd '$rx_reference', $rx_reference; # for debug close $fh_reference_paths; my $b0rken = <<'EOBORKEN'; # paths with appended files, some borked CMD="/unix/path/to/folder/is/herefile_name.sh" #CMD="/unix/path/to/folder/is/herefile_name.sh" XYZ="/unix/path/to/folder/is/herefile_name.sh" XYZ="/unix/path/to/folder/is/here/file_name.ok" CMD = "/unix/path/to/another/folder/some_file.ok" CMD="/unix/path/to/folder/is/here/file_name.ok" CMD = "/unix/path/to/folder/alsosome_file.xy" EOBORKEN open my $fh_b0rken, '<', \$b0rken; my $add = '//'; # make addition evident for development BORKEN: while (<$fh_b0rken>) { $_ =~ s{ \A \s* CMD \s* = \s* " $rx_reference (?! /) \K }{$add}xms; print $_; } close $fh_b0rken; ^Z CMD="/unix/path/to/folder/is/here//file_name.sh" #CMD="/unix/path/to/folder/is/herefile_name.sh" XYZ="/unix/path/to/folder/is/herefile_name.sh" XYZ="/unix/path/to/folder/is/here/file_name.ok" CMD = "/unix/path/to/another/folder/some_file.ok" CMD="/unix/path/to/folder/is/here/file_name.ok" CMD = "/unix/path/to/folder/also//some_file.xy"