The || does not work inside a regular expression (well, it does, but it matches anything). Add some more testing strings. Use single| inside a regex, or use two regexes connected by ||.
The honorable choroba is correct; blame simple carelessness; intermittent, inadequate internet access in my second consecutive month on the road and my plain errror for the wrongful use of ||. As written above it should be a single Vbar; as choroba notes, it could also be written as:
#!/usr/bin/perl
use 5.10.0;
my @work=("I Arranged a meet.", "Transcribe this", "Shud Not MATCH");
for $work(@work) {
if (($work =~ /Transcribe/) || ($work =~ /Arranged/) ) {
say $work;
}
}