#!/usr/bin/perl use strict; use warnings; use autodie; my %replacements = ( 'user.name@domain.com' => 'uname', 'user@domain.com' => 'user', ); open( my $readFile, '<', "sampleFile" ); while ( <$readFile> ) { # if contains :Calendar and is suffixed with / # or :Contacts with same suffix or Users prefixed # with / or is an email-address followed by " = if ( m/:Calendar(?=\/)/, m/:Contacts(?=\/)/, m/(?<=\"\/)Users/, m/.+@.+\"\s=/) { # then replace every occurrence as in list foreach my $key ( sort keys %replacements ) { s/\b$key\b/$replacements{$key}/g; } } print $_; }