Hello theravadamonk,

It’s simpler if you read in a whole message (four lines: Message Time, Mail From, Mail to, quarantine) at a time, and then search for “jay” in one of the addresses. Here is one approach:

#! perl
use strict;
use warnings;
use Data::Dump;

my @message;

READ_FILE: while (<DATA>)
{
    push @message, $_;

    for (1 .. 3)
    {
        last READ_FILE unless defined(my $line = <DATA>);
        push @message, $line;
    }

    if ($message[1] =~ /<jay@/i ||          # Mail From:
        $message[2] =~ /<jay@/i)            # Mail to:
    {
        print "\n", join('', @message);
    }

    @message = ();
}

__DATA__
Message Time: Feb 3 11:24:54
Mail From: <letter@leemaletter.com>
Mail to: <info@example.com>,<jay@example.com>
quarantine: spam-JF6LBytcy_3D.gz
Message Time: Feb 3 11:25:18
Mail From: <noreply@lankaemarketing40.info>
Mail to: <jay@example.com>
quarantine: spam-uXWM3SJ-nlB0.gz
Message Time: Feb 3 11:25:29
Mail From: <bounce@rhmarketing.info>
Mail to: <sam@example.com>
quarantine: spam-uOG8ycqZrq1s.gz
Message Time: Feb 3 11:25:47
Mail From: <Jay@example.com>
Mail to: <userx@gmail.com>
quarantine: spam-FxfQDEDm-5MW.gz
[download]

Output:

12:51 >perl 1624_SoPW.pl

Message Time: Feb 3 11:24:54
Mail From: <letter@leemaletter.com>
Mail to: <info@example.com>,<jay@example.com>
quarantine: spam-JF6LBytcy_3D.gz

Message Time: Feb 3 11:25:18
Mail From: <noreply@lankaemarketing40.info>
Mail to: <jay@example.com>
quarantine: spam-uXWM3SJ-nlB0.gz

Message Time: Feb 3 11:25:47
Mail From: <Jay@example.com>
Mail to: <userx@gmail.com>
quarantine: spam-FxfQDEDm-5MW.gz

12:51 >
[download]

Notes:

1. Case-insensitive matching is achieved by adding the /i modifier to the regex.
2. The above approach will work only if the 4-line messages are placed contiguously in the data file (no intervening blank lines), with the first message beginning on the first line.

Hope that helps,