After some investigation, I notice that some of her messages are "stuck" in the email queues on the server. Since I deal with these sorts of issues often, I immediately suggest double-checking whether the addresses on a few of the stuck messages are incorrect. Although it is not unusual for people to say that they double-checked, often there is a typographical error. "No, that's not it." "Well, OK, at least the syntax of the email addresses seems to be correct. Let's explore some other hypotheses."
Next, I notice that the date on the stuck messages is 12/31/1969; but this is 2008. "Aha!" say I. Perhaps some of the servers at the parental receiving end are not accepting the messages based on the absurd date. And, for those cases where the messages did not appear stuck in the queue, yet the intended recipients still claim that they never got them, very likely they are buried in an automated Junk folder or just at the wrong end of a very large inbox sorted by date. "Obviously, the clock battery is dead on your computer. If you replace the battery and then set the date correctly, this will stop happening." I provide detailed instructions on how to remove the old battery and take it to Radio Shack. "It will cost about $12. Do not tell the person at the store that it happens to be for a Macintosh computer." (Store personnel will invariably say that they do not carry parts for Macintosh computers.) Great! Problem solved ... or so I thought.
A few weeks later, I get another call from the same teacher. "It is still happening." After some back and forth to verify that the battery was indeed replaced and that the computer is now showing the correct date and time, I have to admit that I am stumped. Perhaps there is a wrong date on the school firewall or a proxy server? Perhaps the teacher uses one computer to send the newsletters but a different one for daily work such as individual email? The conversation goes on, via electronic mail, for several more weeks. I am truly baffled. Then one day, it happens, the email equivalent of a casual comment in the hallway: "well, actually, the newsletters are being sent out by the FileMaker server; but that shouldn't matter, should it?" The secret phrase, at last!
Troubleshooting and its software equivalent, Debugging -- whether it is for an electronic mail delivery problem or an overly enthusiastic toaster or a sound system where one channel is silent -- these are the topics and thinking skills that have always fascinated me. Sadly, this topic is not even mentioned in the "core content standards" taught by our schools. Yet, people who are crack troubleshooters become far more valuable employees in practice (whether in IT or in countless other fields) than those who lack this skill but who list A+, MCSE, CCNA, Ph.D. or whatever other forms of certification on their résumés. Often the clues to what is going wrong come from observations of the user, the environment, the organization or the situation, rather than the faulty device itself.
The above anecdote illustrates just one example of a powerful troubleshooting technique. Time and time again, I have noticed that, the moment the user tells you, "bla bla bla, but that shouldn't matter!" you are finally getting very close to the crux of the matter. Invariably, a closer look at whatever it is that shouldn't matter will lead you straight away to what is wrong. It is like that other simple trick -- turning it off, counting to ten, and turning it back on -- which also fixes so many problems. The trick of asking what might have changed that "shouldn't matter" is among the most powerful tools in the kit used by skillful troubleshooters. As easy as this is to understand and remember, it seems almost criminal that we not only do not consider it part of the "core content curriculum" for all students, we do not even bother to share such powerful little tricks and habits of mind with our educators. Anyone who has ever helped another person "fix their computer" has heard this phrase countless times. Why are we keeping this phrase and other tricks of the troubleshooting trade a secret? And where, in our broken education system, are the pundits saying, "bla, bla, bla, but that shouldn't matter?" If we dig deeper around those areas, we are apt to get a clue how to fix this thing. Surely, making Troubleshooting / Debugging a required subject for both students and teachers is going to be part of the solution. But wait, didn't Seymour Papert tell us this, years ago?