How can I have secure internet conversations with my girlfriend at her work that won't raise suspicions with her employer.
January 4, 2008 1:22 PM   Subscribe

How can I have secure internet conversations with my girlfriend at her work that won't raise suspicions with her employer.

My girlfriend and I work at two different school districts as teachers. During our plan periods, we like to share how our day is going. Nothing scandalous, but I like to declare my undying love for her and give her a virtual kiss now and then which I think is none of the districts damn business, so we don't use district email. Her district blocks yahoo, gmail and all the other usual suspects and bans chat, so those are out of the question. We've been using a secure google docs document, but now they have blocked google docs for whatever reason. That way wasn't totally secure anyway because without memorizing the complicated url she couldn't get there via bookmark to the secure version. So it initially opened as http: not https:.

Any sneaky ideas for how to have a secure conversation that wouldn't get her in trouble? My IT department is far more enlightened and easy to work with.
posted by doppler68 to Computers & Internet (24 answers total) 2 users marked this as a favorite
Maybe Hushmail?
posted by sharkfu at 1:27 PM on January 4, 2008

Maybe don't, unless you want to incur whatever sanctions IT can bring upon her. You really don't want to get into a cat and mouse game with IT. IT will always win.

Send text messages from your cell phones instead.
posted by grumpy at 1:32 PM on January 4, 2008

Send SMS messages between your phones. If her school doesn't want her using their network for this stop, that's their right.
posted by nowonmai at 1:32 PM on January 4, 2008

Or you could use the district email and develop a code that only you two know. That way it's fairly simple, and it's an inside thing for just you two.
posted by teleri025 at 1:35 PM on January 4, 2008

What about text messages?
posted by electroboy at 1:35 PM on January 4, 2008

You might be able to access Google Apps, which includes gmail inside of it, even if normal gmail is blocked. You could also try setting up some kind of secure blog that you can post access.

Also, seconding the idea that you should only do this if you're comfortable with facing the consequences if your girlfriend actually does get in trouble for this.
posted by burnmp3s at 1:37 PM on January 4, 2008

I suppose it's not an option for her to look for another job where Big Brother isn't breathing so hard on her neck?

I can think of a few technical solutions. (Hushmail has already been mentioned, GnuPG if she can install software on her computer (or run it from a USB drive), etc.

But I'm in the "don't do it" camp. School districts are traditionally sticklers for the rules, so she'd likely incur the wrath of her district if she's breaking them. Use your cellphones instead.
posted by the cake is a pie at 1:40 PM on January 4, 2008

You could IM with pidgin and pidgin-encryption on both sides.
posted by cdmwebs at 1:43 PM on January 4, 2008

Just wondering, you say they have blocked Google Docs "for some reason" - is it possible they are monitoring her PC, and saw that she was using it for chatting? In which case, tread carefully.
posted by PercussivePaul at 1:51 PM on January 4, 2008

If you're dead set on doing this, you could set up your own private blog (as burnmp3s suggested), or you could go with a less usual e-mail suspect. Google for free e-mail; Yahoo, Hotmail, Gmail, etc, aren't the only ones out there.

It sounds like her district is going through an awful lot of trouble to prevent this, however. Their next step might be to monitor her activity, in which case she's busted anyway. I highly recommend the text message route.

Or maybe one of your schools has horrible cell reception, or cell phones are banned in classrooms. In that case, there's teleri025's secret code solution. That would probably only work for things like sending a kiss; I doubt it'd be worth the effort to develop an entire secret language. :) And if they're reading your e-mail, they'd still be able to figure out that you're saying something private, even if they don't know what it is. So I'm still thinking that if you go the computer route, a no-name e-mail service or blog is your best bet. Good luck!
posted by iguanapolitico at 1:52 PM on January 4, 2008

Set up a password-locked Wiki? Random visitors could just see a blank page, while anyone typing in anything else would see a login page.

...log in, and it's just the two of you commenting & modifying pages as y'all see fit...

If you bought your own domain, you could even give it a fairly work-related title (not a good domain name, mind you, just something you two can remember and which has words like "education" in it so someone watching proxy logs would see a site that sounds work-related).

Of course, this might not be free, what with the hosting & all (plus SSL, if you wanted to go for that). But on the plus side, all you need at-work is a browser.

Naturally, if they're using monitoring tools on the PC itself (rather than just on the LAN) then all bets are off -- they can just watch the screen as if they were sitting right there with her.
posted by aramaic at 1:53 PM on January 4, 2008

Oh, I just read that chat was out of the question. I'm assuming it's because it's blocked on her end. You can tunnel the chat traffic through port 80 (the web port) so it isn't recognized so easily. I'd think this + the encryption would fare pretty well.
posted by cdmwebs at 1:57 PM on January 4, 2008

Send SMS messages between your phones. If her school doesn't want her using their network for this stop, that's their right.

Ding ding ding. We have a winner.

You're deliberately trying to get around IT restrictions. In many places this is grounds for dismissal. Is it really worth doing this?
posted by dirtynumbangelboy at 2:01 PM on January 4, 2008

Response by poster: Thanks to everyone for the answers. I'm prone to agree that it's probably too risky to try any internet solution since they seem to be such sticklers. If they blocked google docs because of her using it for private communications, going with another solution is just escalating the battle with IT. So I'm gonna go with text messaging.

posted by doppler68 at 2:02 PM on January 4, 2008

Twitter! You can use it entirely on the phone to send and receive tweets as SMSes, or on a computer, or both at once. Maybe you on your computer (with your laxer IT dept) and she on her cellphone. This is basically what Twitter is for, isn't it?
posted by evariste at 3:00 PM on January 4, 2008

You are insane. All that communication on school networks is archived and people are keeping tabs of it all. Don't even think of doing that on a school related computer or you are both risking your jobs.
posted by 45moore45 at 3:03 PM on January 4, 2008

You could set up a remote server and ping it using Morse Code. And then SSH in to that server to read the logs and decode the sexy messages.

That would be erotic.

Honestly, I'd say their IT staff has you beat by virtue of being assholes, or more likely, they're overly regulated from above. :(
I like the text message idea.
posted by dosterm at 3:14 PM on January 4, 2008 [2 favorites]

PARENT groups have reacted angrily to revelations that teaching couple The Doppler68s used school equipment to create a secret network so that they could send each other hot love notes during school hours. The pair, who have since been dismissed, created the system to subvert attempts by authorities to protect children from online cyberstalking ...

in other words: use yr phone, ffs.
posted by bonaldi at 3:22 PM on January 4, 2008 [4 favorites]

If her cell phone supports it, Gmail Mobile might be a nice alternative. You get the advantages of text messaging on her side, plus the ease of email on your side.
posted by i love cheese at 3:36 PM on January 4, 2008

a have a few friends who worked in the IT departments of local school districts and i got to hear about all the juicy stuff they saw when remotely connected to teacher desktops... the superintendent's affair was the juiciest. and nobody even knew they were being watched. so my vote goes for text messages
posted by hummercash at 3:54 PM on January 4, 2008

I used to do something very similar by using X-headers to send seemingly innocuous messages with secret messages in them. Basically the email RFC's allow you to set arbitrarily defined headers (similar to To: Subject:) in the format X-Whatever. These don't normally show up in normal view. Combined with the fact that From: headers can be pretty much anything enabled me to send messages that looked like this to innocent eyes:

Subject: Very Important business

Lots of official looking stuff

Viewing message source would reveal:

X-secret-message: Tonight baby, it's me you and, er, the rest of MetaFilter
Subject: Very Important business

Lots of official looking stuff

It's a fairly techy way of going about things, and as a fully paid up geek I have to remind you that security through obscurity is not really security at all. It did well to get passed prying bosses eyes, but it was all there in plain view for anyone who knew where to look.
posted by tallus at 4:08 PM on January 4, 2008 [3 favorites]

At my school, the administrators (of which I am one) have network rights to look at the teachers' computer screens and see what they are doing at any time. I have never done it because I'm too busy doing real work but I know my boss does it all the time. Most school districts make you sign an internet use agreement so I wouldn't chance it. One of our office staff was almost fired last year because she was sending too much personal email.
posted by tamitang at 6:01 PM on January 4, 2008

Heed the warning/advice from tamitang.

At one school district where I worked, ANY e-mail was subject to review (reading, archiving by IT and any admin who wanted to see it). It also was considered "property" of the district, not the individual. All employees also had to sign an internet use agreement. In other words: Don't risk email. Use your cell (and brain cells).
posted by Smalltown Girl at 9:34 AM on January 6, 2008

Is Meebo blocked?
posted by herbaliser at 11:35 AM on January 7, 2008

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