For those who are interested, I've included my final source. There's support for mr_mischief's third party by storing an email address in $authority. Of course, the e-mail credentials file is for a Santa-only account and is chmodded to 600.

#!/usr/bin/perl -w
use strict;
use List::Util qw(shuffle);
use Digest::MD5 qw(md5_hex);
use Net::SMTP::TLS;

# Parameters
my $authority = '';
my $value = 10;
my $participantsFile = 'santaList.txt'; # Name#email\n
my $previousFile = 'lastYear.txt'; # sorted md5 hashes\n
my $serverInfoFile = 'emailCredentials.dat';

# Declare variables with file-wide scope
my (%emails, @names, %matching, @previous, @content);


# Initialize data
open INPUT, '<' . $participantsFile;
while (<INPUT>) {
    chomp;
    my ($name,$email) = split '#';
    $emails{$name} = $email;
}
close INPUT;
open INPUT, '<' . $previousFile;
while (<INPUT>) {
    chomp;
    push @previous,$_;
}
close INPUT;

# Generate the list
@names = keys(%emails); # Collect the list of all participants
GENERATE: while (1) { # Picking loop
    @matching{@names} = shuffle(@names); # Match 'em up
    
    # No one has themselves
    foreach (@names) {
        next GENERATE if $_ eq $matching{$_};
    }
    
    # Generate digests for comparison
    my @digest = ();
    foreach (@names) {
        push @digest, md5_hex($_, '=>', $matching{$_});
    }
    @digest = sort @digest;
    
    # Compare against previous year's results
    my $index = 0;
    foreach (@digest) {
        while ($index < @previous and $_ gt $previous[$index]) {$index
+++}
        last if $index == @previous;
        next GENERATE if $_ eq $previous[$index];
    }
    
    #Passes - store the digests for next year
    open OUTPUT, '>' . $previousFile;
    print OUTPUT join "\n", @digest;
    close OUTPUT;
    last GENERATE; # Passes
}

# E-mail the results
{
    open INPUT, '<' . $serverInfoFile;
    my $host = <INPUT>;
    chomp $host;
    my $port = <INPUT>;
    chomp $port;
    my $user = <INPUT>;
    chomp $user;
    my $password = <INPUT>;
    chomp $password;
    close INPUT;
    my $server = Net::SMTP::TLS->new(  $host,
                                       Port    => $port,
                                       User    => $user,
                                       Password=> $password,
                                    )
        or die "Can't open mail connection: $!";

    # Independent auditor
    if ($authority) {
        @content = ();
        $content[0] = "The picks for this year\'s gifting are as follo
+ws\:";
        foreach (@names) {
            push @content, "$_ is giving to $matching{$_}";
        }
        send_mail($server, $authority, $user, 'Secret Santa Drawing', 
+@content);
    }
    
    foreach (@names) {
        @content = ();
        $content[0] = "Dear $_\,";
        $content[1] = "";
        $content[2] = "Thank you for participating in this year\'s Sec
+ret";
        $content[3] = "Santa gift exchange\.  This year\, you will be 
+giving";
        $content[4] = "a gift to $matching{$_}\.  Please remember to l
+imit the";
        $content[5] = "monetary value of any gift you give to \$$value
+\.";
        $content[6] = "";
        $content[7] = "Happy Holidays\,";
        $content[6] = "Robo-Santa 5000";
        send_mail($server, $emails{$_}, $user, 'Secret Santa Drawing',
+ @content);
    }
    $server->quit;
}


sub send_mail {

    my($server, $to, $from, $subject, @body) = @_;
    
    $server->mail($from);
    $server->to($to);
    $server->data();
    $server->datasend("To: $to\n");
    $server->datasend("From: $from\n");
    $server->datasend("Subject: $subject\n");
    $server->datasend("\n");
 
    foreach (@body) {
        $server->datasend("$_\n");
    }
    
    $server->dataend();

}
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