Keylogging my son's mac
February 14, 2011 10:01 AM   Subscribe

I suspect my young son is carrying on an ongoing discussion with a stranger he met on the internet. My wife and I are going to approach him, but we would like some evidence so we know what questions to ask.

This is my fault for not watching more closely, so this is a good wake up call. My wife and I have decided we need more evidence, so we are wondering what options are available to us.

We brought up the idea of key logging, and we feel that this would capture the most data, especially the transcript of what he is typing. We are fairly tech-savvy when given proper guidance, so we are wondering what is the best option available to us to stealthily capture his keystrokes undetected on his mac computer? We have physical access to his computer and are willing to spend money on this. Thanks.
posted by anonymous to Computers & Internet (41 answers total) 3 users marked this as a favorite
What do you mean by young? Is he 8 or 17?
posted by roomthreeseventeen at 10:02 AM on February 14, 2011 [1 favorite]

As a kid who spent a lot of time knowing that my dad had a keylogger on all of my computers, may I politely suggest that you just ask him?

I still resent my parents for trying to spy on me when I was a teenager. If they had just respected my privacy and asked what I was doing, I would have gladly told them.
posted by thsmchnekllsfascists at 10:03 AM on February 14, 2011 [44 favorites]

You are not going to get good replies to this question.

As a rule, this site tends to come out strongly in favour of open and constructive dialogue rather than clandestine surveillance followed by ambush.

May I respectfully state that in the absence of extenuating circumstances (very young, particularly vulnerable, etc.) that I tend to agree with this line of argument.
posted by dmt at 10:05 AM on February 14, 2011 [16 favorites]

Have you checked whatever program he's using to see if conversation logs already exist?
posted by onhazier at 10:07 AM on February 14, 2011 [2 favorites]

Before you move to a key-logger, just ask him in general about his habits. Just show some interest and see if he opens up. "Whatcha doing there, buddy? Having fun? What site is that? Is that like Facebook? Talking to someone? One of your friends from school? I wish I had the Internet when I was your age."

The next step, if you're really concerned, is to move the computer into a public place, like the living room or kitchen.

If all of that is still not making you feel safer, then use a USB key logger.
posted by Cool Papa Bell at 10:08 AM on February 14, 2011

Is there a way to handle this other than through covert surveillance? There's really no way that's going to end well. FWIW, I'd start with a conversation.
posted by londonmark at 10:09 AM on February 14, 2011 [1 favorite]

My wife and I have decided we need more evidence, so we are wondering what options are available to us.

Why do you feel like you need more evidence? Is this something you asked him to stop doing already, but now he's doing "behind your back"?

I also concur that we need more clarification about "young" - his age makes a real difference here.

Also, is this person a "stranger" to all of you? Is it a stranger who says they're an adult, or a stranger who says they're a child? Is it possible that this person is a stranger to you, but not to your son - because they have shared friends through classmates, etc? (ie: someone who can be vouched for as "real" though normal networks.)

So, my advice:

1) Ask him about it. Use open ended questions, and try to do more listening than talking, at least in the first part of the conversation.

2) Talk with him frankly about what your fears are.

3) Contact the "stranger" (if an adult) and ask them for a phone number so you can talk with them. The "stranger" might not realize they're talking with a minor.

4) Prohibit your son from using his computer anywhere in the house other than in a public space (ie: the kitchen or living room with parents present.)

5) Ask your son to share the emails and/or chat transcripts with you.

A keylogger really isn't the answer here.
posted by anastasiav at 10:10 AM on February 14, 2011 [2 favorites]

Google "mac keylogger" and you will get several options. This appears to be popular. Test them first on your own computer.
posted by Brocktoon at 10:10 AM on February 14, 2011

When my mom installed a keylogger on our family computer, she used Spector - here is the Mac version.

Please Mefimail me if you are interested in my feeling when my mother confronted me with information that she obtained on this keylogger - I suspect I was older than your son at the time, but not by much.
posted by muddgirl at 10:13 AM on February 14, 2011 [10 favorites]

Okay, don't stealth any of this. Like as not they're just talking about normal age-appropriate stuff, and the more you try to keep an all-seeing eye on him the harder he'll work to avoid it and the less he'll trust you.

Instead, ask him:

-what he knows about the other person (name, email address, location, age)
-what the other person knows about him (same)
-what they talk about

And maybe have a discussion on general internet safety, and how he should assume anything he posts online can be viewed by anyone, forever, so be careful. And if he's ever worried or feels threatened by something online, he can come to you for help.

Also maybe ask for the online friend's contact information and maybe his username/frequented sites, but swear up down and sideways you will only use it for an emergency, not to nose around in their online business looking for things to worry about. And keep your word on that.
posted by Metroid Baby at 10:15 AM on February 14, 2011 [3 favorites]

Ongoing discussions with strangers is a lot of what the internet is for. And for young (?) children, the internet is what parental supervision is for. You've said you were under-involved; don't then overcompensate with surveillance software. Just provide an appropriate level of supervision and involvement. Maybe set up some new ground rules, like no secret internet time, or whatever age-appropriate rules might apply.
posted by pajamazon at 10:16 AM on February 14, 2011 [3 favorites]

The post author does not appear to be asking for parenting advice...
posted by Brocktoon at 10:19 AM on February 14, 2011 [10 favorites]

You know, on a second read-through, I see that your question was pretty specifically about what software to use, not a general what-to-do. So, sorry for the non-answer!
posted by pajamazon at 10:22 AM on February 14, 2011

Seems to be this issue is very wide until we know what age your kid is. If he is really young then he probably shouldn't be spending unsupervised time on the internet at all. If he is moderately young you should have a discussion about how the internet creates endless opportunities for people to misrepresent themselves.

I think what you have here is a dead horse question in that most of us will advocate open communication as opposed to privacy invasion. If you ambush your kid with evidence-supported accusations his mind will settle on a feeling of betrayal and focus on the real issues will be lost.

Unlike a lot of the earlier posters I won't ask you a slew of questions because I see you have posted this as anonymous. Some factors you have to understand include the fact that if your son doesn't have a good picture of who he is talking to it is also possible that the person he's conversing with does not know your son is a child. Another is that if you are building 'evidence' against a child predator you should have already involved the police who can gather more evidence in an afternoon than you can in a year and without further involvement on your son's part.

I suspect that your entire situation could be solved with a frank discussion with your kid. Even really young kids can surprise you when you treat them with the respect you give adults.
posted by Gainesvillain at 10:25 AM on February 14, 2011

Mod note: few comments removed - if you can't answer non-snarkily, you need to go away from this thread. OP needs advice. It's okay if the advice is "dont do this" and not okay if the advice is "you're a bad person"
posted by jessamyn (staff) at 10:27 AM on February 14, 2011

I will be flat honest, many will probably be upset with this approach, ten years or so ago this is what I did when my mother feared my younger sibling was doing this.

My mother had warned my younger sibling about all the dangers, moved the computer to the kitchen, etc.

I contacted them as a person of the opposite sex around their age. Said different things that would convince them to meet me in person, and then set the meeting up at the mall.

My younger sibling went to my mother for a ride to the mall and some money (my mother was aware of why my sibling really wanted to go), my mother inquired the reason for the mall trip and of course my sibling gave a false reason.

Once they were in the meeting spot I showed up, and I didn't 'embarrass' them, it's not as if all the mall passerbys knew my sibling, etc. but I explained I was the other person and that this could have been much much worse.

The sibling was horrified by what occurred and realized the realities of what could have happened.
posted by aorkis at 10:33 AM on February 14, 2011 [12 favorites]

Go easy on the OP - I have an Aspie/ODD teen at home, and yes, there are circumstances which warrant surveillance, especially when you have a teen who needs social interaction and yet cannot always be relied upon to recognize ill intent on the part of others.

I use Network Monitor Home by Mingsoft - http://www, - no installation on any computers in the home, other than the computer doing the monitoring. There is a little network configuration which needs to be done, but I got it up and running in a matter of minutes. Don't know if there is a mac version (for the monitoring comp) but the other computers on the network can be any OS. Good luck!
posted by brownrd at 10:34 AM on February 14, 2011 [1 favorite]

I (an adult) recently started chatting online with someone whom I discovered was much younger than me (ten years old) in another country. I was a little surprised that A) she would even bother and B) that she wasn't better supervised, but mostly she's just interested in practicing her English and talking about Justin Bieber, so I don't feel there's anything I have to worry about. I have been saving transcripts of our conversations just in case her parents ever get concerned and contact me. I'm just pointing out that older internet strangers are not necessarily all creepazoids.

Anyhow, by sneaking and spying and (eventually) confronting, you are setting a hazardous precedent by which your son will just work a lot harder to conceal anything he feels might upset you. This is an opportunity to talk with him and teach him things.

If you already have evidence that there is some sort of potentially illegal or harmful contact occurring, then that's one thing. If you don't really know what the situation is, then your son is the person with all the information, you should ask him.
posted by hermitosis at 10:36 AM on February 14, 2011 [1 favorite]

First let me state that I have never had a keylogger on any computer, but I can see good reason to have one. Depending on this child's age, what if they want to let him make mistakes, but want to be there in case he makes a big one. They let him have rope and never mention it to him. Or, if they find out he is giving out his personal information to a true stranger they could have a general internet discussion with him and can also keep an eye out to make sure there were no ramifications from the release of personal information. Let him have rope, but prevent him from hanging himself so to speak. I do think at a certain age and I do not know what that age is because I think it is highly dependent on his own maturity level, then you remove the keylogger and hope your lessons were learned well. At a very young age, this is not about trust, it is about teaching them safety. Just as you would not want your 7 year old to cross a busy street on his own, you might consider watching him do it a few times and then letting him do it on his own.

So, I guess to me the question is how old is you child and what is his maturity level?
posted by AugustWest at 10:36 AM on February 14, 2011 [1 favorite]

When I was a teenager, I had an online friendship with an older stranger I had met over the internet. That friendship was an mitigated good, and it helped me through some very difficult times. I think about him a lot and I only appreciate more in retrospect how necessary friendship that was.

On the other hand, he was across the ocean, so there was zero percent chance of "stranger danger" or whatever, so YMMV.

You should definitely ask your kid about his online habits before installing a keylogger. If (or, frankly, when) he finds out about the keylogger afterwards, there will be negative consequences.
posted by Sticherbeast at 10:46 AM on February 14, 2011

When I was 14 I joined an online community and made friends with a lot of older people. I still remember their usernames, though I never met them or found out what their real names were. (Except one, who I got dinner with last year when he was in the area- I'm 23 now!)

I was a bit of a misfit in school, and being friends with all these fun, interesting older people made me feel good about myself. I stopped going to the community a few years later, but I truly feel that being a member helped me grow into a more thoughtful person. It also really helped my self-esteem at a time when I really needed the help. My parents knew I was an active member of this community and they encouraged my involvement.

It's fine to be concerned, but you should understand that online friendships can actually be really great for kids.
posted by showbiz_liz at 11:39 AM on February 14, 2011 [9 favorites]

So you are asking a bunch of strangers on the internet for advice on how to collect evidence of your son's discussions with strangers on the internet?

I say that to point out that while there are certainly some bad scenarios to worry about, the possibility that your son's communications are entirely benign ought to be given some weight. If your son is old enough to understand the full implications of where chatting on the internet with strangers might lead, then snooping/keylogging doesn't seem like a great way to foster a relationship of trust with someone who will shortly become an adult. If your son is too young to understand the implications, then he shouldn't be on a computer unsupervised, period.

Consider: once you snoop, you've lost moral high ground. And if you find nothing of concern, you've lost moral high ground for nothing. Or you could respect your son's fundamental dignity and talk to him first.
posted by ambrosia at 11:42 AM on February 14, 2011 [4 favorites]

Another option for keystroke logging on a Mac is Keyboard Spy. Something you should know is that most if not all of the commercial software you'll find won't stay hidden against a savvy user. If you're going to go seriously covert you'll need to consider installing some kind of rootkit (along with the ethical complications others have already been so vocal about). Unfortunately the best archive of rootkit software is a, which if you've been following the news at all was compromised during the recent Anonymous/HBGary incident. So that's down until further notice. Which is probably for the nest; it may be legal but at some point the kid's going to find out you've been spying on him & the fit's gonna hit the shan.
posted by scalefree at 11:54 AM on February 14, 2011 [1 favorite]

I would give your son the opportunity to "do the right thing." Confront him with your suspicions. Give him a chance to explain what's going on, and then if the story seems reasonable, do your due diligence with the party on the other end of the connection (for example, my son, now 16, has Skype buddies in Brazil and elsewhere that he's acquired through places like Habbo--I've spoken to the kids, and their parents, and I glance briefly at the occasional video chat when I happen to pop into the room to assure myself that everything's on the up-and-up without completely invading his privacy) It's the same deal with my 13-yo dau, who pretty much limits her internet contacts to kids she knows from school. This is the ideal outcome--you've added to the trust level rather than taken away from it.

If the story doesn't add up, then let him know that you will be either installing a keylogger or requiring that internet access take place in a public space, just to be sure. However, if you sneak around behind their back to get the goods, they are sure to sneak around behind your back to avoid detection. Any kid who is middle-school age or older can find ways to get unsupervised internet access if they really want, to be doing things you don't want them to). A war of stealth escalation is really hard to win.
posted by drlith at 12:00 PM on February 14, 2011

my parents spied on me online so i got better at hiding what i did. i wasn't doing anything to be concerned about when they started spying. by the time i got myself into some real trouble, the lines of communication had been shut down and i felt like i couldn't talk to my parents because they'd overreact instead of help. a lot of the friends i met online were in similar circumstances. whatever technology you use, he'll find a way around it eventually and you will have lost the war.
posted by nadawi at 12:31 PM on February 14, 2011 [22 favorites]

I used Spectorsoft on my son's computer from the moment he got it until he turned age eighteen. Parents have to protect their children. This was one of the ways I chose to protect mine. He always knew it was there, and we had some frank discussions about what was "right" and "wrong" with respect to online relationships and how much you should share with another person. I don't regret it for a moment, and highly recommend it for gathering further information if your parental spidey-sense is going off.
Don't get me wrong, I didn't use the program to delve into every last intimate detail of my son's online life. I had key words that I searched for, and I wanted to know what sites he was visiting. My son would be the first to tell you, that I didn't say a damn word to him when he started looking at booby sites. That was none of my business. My business was to protect him from predators, insure his privacy, and moreover, keep him from accidentally downloading malware onto his computer.
posted by msali at 12:53 PM on February 14, 2011

I understand your concern, but I'd also recommend just talking to him first.
"Collecting more evidence" and then confronting him about it seems, well, confrontational. He's probably going to feel ambushed and it won't occur to him that you just have his best interests at heart. Then he'll feel wronged and isolate himself from the parents "he can't trust" and he'll seek guidance and support from yet another stranger.

You attract a lot more bees with honey.
posted by Neekee at 1:51 PM on February 14, 2011 [1 favorite]

Without knowing what you mean by "young son", any advice is likely to miss the mark but I'd have to agree with other commenters that going straight for the keylogger is likely going to result in him finding ways around it.

You're much more likely to arrive at a solution together if you approach him with respect and talk it out with him (and yes, as others have said, letting him do more of the talking and you doing less of the lecturing).

If he's old enough then perhaps you could even do some possible role playing to try and get across your fears (play both good and bad internet friends though since there are definitely both kinds online). Not all people have bad intentions, some do, of course, but most people do not.
posted by fenriq at 2:09 PM on February 14, 2011

I just want to add another piece of anecdotal data. When I was 12-16 I was sorta awkward and didn't have many friends at school (in addition to other things like being really depressed). My parents had absolutely forbade me from talking to strangers on the internet so talking to them about it would have been a big no-no and would have probably made it so my biggest source of positive social interaction was taken away. Whenever I felt my parents might be sneaking around the internet I learned how to beat the system. No offense but chances are your kid is more technologically savvy than you if you have to ask Metafilter about which is the best keylogger to use.

Anyway, my online friends... I did a few dumb things but everything turned out alright because chances are my friends were just who they said they were. I don't know the statistics of who is grossly misrepresenting themselves online v. who isn't but I'm fairly certain the media makes the problem seem much worse than it is.

If my parents had taken away my means of communication to my friends I would have been devastated.

Maybe just have an honest conversation saying you approve of them having online friends but you don't want them telling others their last name, their address, phone number, posting personal details online, whatever. But keylogging will shut down any communication you might be able to still have with the kid. Even if you don't actually approve of them having online friends you might want to lie... I'm telling you from experience, they will definitely have them anyway (especially if the friendships are already well established) and would you rather them hide it completely or would you rather have a potential for a dialogue?

And by the way, if you think your kid is the most trustworthy being on the planet and believe him or her about everything, don't. My parents think I am the epitome of trustworthiness and there are sooooo many things that they have no idea about. Why do I keep things from them? Because I know they will disapprove. If you want honesty you can't forbid everything that they are likely to do anyhow or they will never tell you anything.
posted by tweedle at 2:12 PM on February 14, 2011 [4 favorites]

Regarding a previous poster's comment of "once you snoop you've lost moral high ground": parents and children are not equals. Parents have a right and a duty to do what is necessary to protect their kids. The moral high ground is whatever is necessary to ensure safety.

My dad used to record all of the phone calls in our house with a simple device purchased from Radio Shack. He found out some important information about my sibling's extra-curricular activities and was able to step in and make changes. And knowing that the recording device existed helped keep me out of trouble.

It was before cell phones and all, which admittedly would have made his contraption worthless, but I'd think this would be a similar situation. It really depends on if the kid respects you as a parent or not.
posted by tacodave at 2:36 PM on February 14, 2011 [1 favorite]

Like others have said, it really depends on the age and content of the child and talks. If your elementary school child is giving away your address to adults on the internet: we have a problem.

I also want to say that the media, as far as my experiences go in conjunction with what tweedle said, has vastly overplayed this issue. When I was in middle school I met strangers that I had met online without my parents knowledge. It went fine, and in fact this "chance" encounter of mine really came to define my time at home. Could this have gone terribly wrong? I suppose so, but I had common sense and rationalized that my chance of safety was good enough when I looked at the situation beforehand. Yes, everything could have still gone wrong and I could have been abducted, but I also could have been hit by a car while walking on the sidewalk but thats not going to keep me from walking on the sidewalk.
posted by SollosQ at 3:24 PM on February 14, 2011

Many parents use things like keyloggers because they are very afraid and do not know what else to do. You mention that money isn't a problem, but I wonder if you're not seeing that it could cost you a LOT MORE than $19.99. Talking to your son is an option that will significantly reduce the likelihood that this will cost you a good relationship with your son.

When your son realizes what's going on (and he probably will), he will feel not trusted (and he will probably wonder why you didn't choose to just talk to him about it), and he will in turn not trust you enough to share the truth with you. This single choice of yours, as parents to your son, could have permanent effects on your relationship with him for the rest of your lives. Your son needs your guidance as a model for good interpersonal interactions, and you have an unparalleled opportunity here for the good of teaching him about clear and honest communication, assertiveness, trust, awareness, safety, empathy, and concern for others! Kids/teens just plain DO NOT react positively to alarmism or hyperreactivity from their parents, and often will just disbelieve that your concerns have any credibility when presented this way, and then they will push back harder so that the wedge will be driven further between you, because they feel like they're not being respected. Talk to him, say that you're concerned and just wanting to know more about what's going on, not just because you want to know but because you want him to understand how much you care about him and his well-being.
posted by so_gracefully at 4:28 PM on February 14, 2011 [8 favorites]

I don't know why you feel like you have to resort to a key logger, but I want to mention something that I hope you'll consider:

When I was in junior high, my mom read my diary. I was furious. I felt betrayed. I felt like my mom couldn't trust me. It took a very long time for me to get over it, even though there was nothing in that diary that would get me in trouble. My mom told me she regretted reading it later.

At the time I already had constructive online friendships. I talked to some of them about the same things I would write about in my diary: How it felt to be a sick only child, the latest fight with my mom, the neighbor boy sucks, oh how do you know if you're gay...

If my mom had read those conversations I would have been just as furious. It would be as if she read my diary again. Or as if she had clandestinely eavesdropped on a private conversation I was having with a real-life school friend.... Luckily, I don't think she ever did. She mostly left me to myself and I never got into any trouble online, and those friendships helped me through some hard times.

There are other options besides a clandestinely installing a keylogger on your kid's computer.
posted by Kutsuwamushi at 4:30 PM on February 14, 2011

I'm part of the first generation of parents who's kids have grown up on the internet. They are 19 and 17 and the 17 year old is up in her room with her PC, doing who knows what. I think I'm raising her well enough so that she won't do anything too stupid. *

From the time my kids were old enough to spend time online I always told them this- "I will not snoop unless I strongly suspect you are doing something that could get you hurt". Even then, I'd never resort to a key logger. I also treat their room and personal possessions with the same amount of respect. From what I can tell, my kids trust me and my wife a lot, certainly much more than I ever trusted my parents.

Talk to your son, don't spy on him. Give him the tools to allow him to make the right decision, including the decision to talk to you if something bad might be happening. When he finds out you logged his private conversations, you could lose his trust forever and he might not come to you when he really needs your support. And 20 years from now he'll still be telling that story with bitterness in his voice.

You didn't mention how old your son is and it makes a difference. If he's under 14 or so, the computer should be in a public place and you should make it a point of walking by occasionally. Of course he's looking at porn, in the 70's we had to go to the truck stop to find porn. If he is older and his behavior is generally good, then let him be a teen. Just warn him about the illegal things that he might not even know about. He needs to know that even if a girl his willingly sends him topless photos, he can still get in trouble.

Talk, don't snoop.

*if JohntheContrarain' exists, I will deny ever writing this.
posted by JohntheContrarian at 6:06 PM on February 14, 2011

my parents spied on me online so i got better at hiding what i did. i wasn't doing anything to be concerned about when they started spying. by the time i got myself into some real trouble, the lines of communication had been shut down and i felt like i couldn't talk to my parents because they'd overreact instead of help.

Please, please, please pay attention to this incredibly important point from nadawi. It's not just that spying on your child is theoretically problematic in the short-run; it's that it can be a major part of establishing a unhealthy dynamic that can have negative reverberations for years to come.

My parents didn't directly spy on me as a kid (no internet at the time!) but there were enough instances of them being unduly suspicious and/or overreacting and/or being inconsistent about relatively minor problems that I learned by the time I was about 16 NEVER to go to them with real problems, because I figured I'd be shamed or thrown out of the house. This meant that I endured some genuinely major, awful stuff without their knowledge or support at 17 and 18. I love my parents and they love me, but that lack of trust and communication at that age established a dynamic that has colored our relationship for more than two decades.

Please consider going down a different path with your son. There is simply no substitute for open, safe, healthy communication between parents and children.
posted by scody at 6:06 PM on February 14, 2011 [21 favorites]

I installed logkext on my mac a couple of years ago and it works well. My kids are older now and I don't look at it very often anymore but when they were first creating their own online lives I felt it was important to know who they were talking to and what they were signing up for. Understand that I have *always* made it clear to them that nothing they do or say online is private and they should behave as though I and their teachers and their friends' parents can all see what they are saying. I do the same. Also, all of our computers are kept in public areas of the house. My kids have old-school privacy but there's no such thing as online privacy and letting kids grow up thinking there is leaves them vulnerable to hackers and people like Mark Zuckerberg and whoever follows in his footsteps.
posted by headnsouth at 6:29 PM on February 14, 2011 [3 favorites]

A more gentle way of approaching this could be to use OpenDNS. Assuming he's using your home-network, you configure your router to use the OpenDNS service (which is free for households). You can keep track of sites being visited, and choose to block some categories; which can range from individual sites to categories (video sharing, p2p etc). If you mistype an address in, you will most likely get an OpenDNS splash page/search page with suggestions - so it is worth mentioning to him, that you are using it. There are, however, technical arguments for using it - I've read that it is quicker for example. OpenDNS are quick to block most free proxies, as they crowd-source popular proxy sites (however you can still use a VPN tunnel; but it's unlikely he's paying for that service).

I'm not suggesting that this will prevent him from engaging in activity that you are concerned about (though in theory you could lock your network down so he can only read metafilter). However, setting up OpenDNS could provide a backdrop to discuss the issue of web security, etc and things to be aware of.
posted by a womble is an active kind of sloth at 6:42 PM on February 14, 2011 [1 favorite]

N'thing simply don't do this. You want be an example for your children by your actions. Do you want to teach them its ok to spy on others that you don't trust, or be open and direct and someone that can be approached about anything? What's done already is unfortunately done. Be ready to remove internet privilages before being covert. Invasion of privacy is a good thing, but this sort of thing is taking it a tad far. You can guage honesty in many other healthier ways than spying.
posted by samsara at 7:12 PM on February 14, 2011

If I were the kid here, this would be a pretty huge breach of trust--trust which would not be earned back. After that, I would find a workaround and be vigilant and not allowing you to spy on me, and I would be sneakier and more tech-savvy than you.

If I were you, I would approach him first. If you still have good reason to suspect that he's being evasive and engaging in risky behavior, then hack his computer.
posted by J. Wilson at 8:51 PM on February 14, 2011 [4 favorites]

Oh, I hope you are not so discouraged by the side-answers to your question that you aren't taking them to heart. Please listen to what the other posters are saying here regarding your interactions with your son. His age would have been very helpful (you can email a mod to answer for you if necessary).

I am not sure if you recognize the negative effect this could have on you and your son's relationship. Keylogging will not only record his private conversations but also search keywords he uses and private questions he may be trying to find the answers to.

I understand the position that many people take that children's privacy is less important than their safety, but I believe there are better ways to help. Talk to your son about internet safety; explain to him that anyone can say anything and that it's impossible to really verify it. Open a line of dialog about what sites he likes to visit or what kind of people he likes to talk to.

I don't believe the correct way to fix this behavior of his is to install a keylogger and present proof that he's been chatting online. If you don't want him chatting at all, restrict access to the internet. Does he have a computer in his room? Put it in the living room.

You obviously use Metafilter so you recognize that there are many good people on the internet. Not all relationships online are to be squashed. We may be strangers but we aren't dangerous.

You said specifically that you are trying to gather evidence so you know what questions to ask. Here are some questions you can ask even without evidence:

"Have you ever checked out ______(site x). I just read about it today and apparently it's really popular with kids your age. Oh, you haven't tried it? What websites do people in your class like to use?"

"Hi son, I was thinking today that we haven't really had a talk about being online. Do you have a minute? I know you spend a lot of time online and that you're really good at computers, but I just want to make sure that we have this conversation so I feel better."

"So, son, I know you spend a lot of time online. What do you and your friends like to do? Do you play a lot of games? Oh, you do, what kind of games? Are you able to talk to the other person? That must be neat! What kind of people are usually playing? What do you talk about? That's cool that you met some Russian guy. What are his interests? Just remember, web safety sounds lame but it's really important. Here's some ways to help make sure to stay safe online:....."

If you had been my parent you could have surmised that I was spending time chatting with strangers online since the time I had been able to go online. However, if you had presented me with all of my transcripts I would have been so incredibly mortified three things would happen: first of all, I would find a way around it. Second of all, I would have been very angry and felt betrayed. Third, I would have held a grudge for years and we would have had an acrimonious teenage experience.

There are better ways to go about this than spying and pushing your evidence at him. Please consider them.
posted by amicamentis at 9:27 AM on February 15, 2011 [2 favorites]

We are fairly tech-savvy when given proper guidance

If your son is the same way, and he suspects that you've installed some sort of keylogger or are capturing network traffic, he will be able to defeat it, even if he doesn't know for sure what you're doing.
posted by one more dead town's last parade at 7:58 PM on February 15, 2011

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