G'day RonW,

Welcome to the monastery.

You really need to show your real test (and its results) or a short, self-contained example which reproduces what you're describing.

I'm wondering whether you're testing the truth of the match or the truth of the captures. Here's an example:

#!/usr/bin/env perl -l

use strict;
use warnings;

while (<DATA>) {
    if (/\s([#]\S)(.*)/) {
        print 'MATCH: TRUE';

        if ($1 && $2) {
            print '$1 && $2: TRUE';
        }
        else {
            print '$1 && $2: FALSE';
        }

        print "\$1='$1'";
        print "\$2='$2'";
    }
    else {
        print 'MATCH: FALSE';
    }
}

__DATA__
123/; #<
456/; #< a comment
[download]

Output:

MATCH: TRUE
$1 && $2: FALSE
$1='#<'
$2=''
MATCH: TRUE
$1 && $2: TRUE
$1='#<'
$2=' a comment'
[download]