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Privacy Encryption

Keeping Your Data Private From the NSA (And Everyone Else) 622

Posted by Unknown Lamer
from the secret-nsa-quantum-computer-knows-all dept.
Nerval's Lobster writes "If those newspaper reports are accurate, the NSA's surveillance programs are enormous and sophisticated, and rely on the latest in analytics software. In the face of that, is there any way to keep your communications truly private? Or should you resign yourself to saying or typing, 'Hi, NSA!' every time you make a phone call or send an email? Fortunately there are ways to gain a measure of security: HTTPS, Tor, SCP, SFTP, and the vendors who build software on top of those protocols. But those host-proof solutions offer security in exchange for some measure of inconvenience. If you lose your access credentials, you're likely toast: few highly secure services include a 'Forgot Your Password?' link, which can be easily engineered to reset a password and username without the account owner's knowledge. And while 'big' providers like Google provide some degree of encryption, they may give up user data in response to a court order. Also, all the privacy software in the world also can't prevent the NSA (or other entities) from capturing metadata and other information. What do you think is the best way to keep your data locked down? Or do you think it's all a lost cause?"
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Keeping Your Data Private From the NSA (And Everyone Else)

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  • by For a Free Internet (1594621) on Wednesday June 12, 2013 @11:51AM (#43986307)

    It stinks, but I can see if anyone's been intruding. So far it is totally secure.

  • by kullnd (760403) on Wednesday June 12, 2013 @11:54AM (#43986349)
    Only way you can keep your data yours while sitting at rest is to have it on your own servers and utilize proper encryption and security on those servers. That means don't use "cloud" anything unless it's on equipment you own, run your own email servers, etc. Remember that even doing this, emails that you send to other people can be accessed through whatever servers they use.
    • by Bearhouse (1034238) on Wednesday June 12, 2013 @12:19PM (#43986779)

      Yes, which is why i've been using PGP for emails to/from my more nerdy family and friends for a while.
      Used to be a free plugin for those of us cursed with using Outlook, now paid.
      I should take a closer look at this, I suppose:
      http://code.google.com/p/outlook-privacy-plugin/ [google.com]

      Of course, other options exist. Enigmail for Thunderbird works OK too, apparantly...

      Is it just me, but how hard would it have been for Microsoft, Apple & Lotus/IBM to have rolled this type of functionality into the base product?
      (And don't tell me a corp like Exxon or whatever would find it too hard to swap certificates with its major supplier & customers, also presumably mostly big corporations with a vested interest in keeping their emails secure)
      Why did they not, eh? Conspiracy theorists, off you go!

      • by cdrudge (68377) on Wednesday June 12, 2013 @12:29PM (#43986949) Homepage

        But the NSA says it's just collecting the metadata on communications, not the actual communications. So while encrypting the message in your email may prevent them from (easily) reading your email, they still see that you sent or received an email and who it was coming or going to.

        • by meta-monkey (321000) on Wednesday June 12, 2013 @12:49PM (#43987289) Journal

          And encrypting it screams "hey look at me look at me I'm saying something I don't want you to know about!"

          • by bill_mcgonigle (4333) * on Wednesday June 12, 2013 @02:04PM (#43988287) Homepage Journal

            And encrypting it screams "hey look at me look at me I'm saying something I don't want you to know about!"

            Huh? My mail server has been opportunistically encrypting all MTA traffic for the past decade and all of my remote access is via OpenVPN or ssh. My work involves conversations with clients that include, but are not limited to trade secrets, personally-identifiable medical records, and financial information. Damn right I don't want other people to know about that stuff, and the NSA is near the bottom of that list.

            The only change I'm going to make over this NSA tussle is to stop accepting plain HTTP on my own infrastructure. Sorry, IE on XP users - you're out of luck. The other 95% of the web will be better off if everybody makes the same change.

            I'll have to look through my logs to see if the same change can be made for mail yet.

          • by Dr_Barnowl (709838) on Wednesday June 12, 2013 @02:08PM (#43988323)

            Right now it screams "I've heard of PRISM".

            Now is the best time to start routinely encrypting your communications, because you have a plausible reason to do so.

        • by AmiMoJo (196126) *

          There used to be anonymous remailers that accepted encrypted messages. You encrypted once with the recipient's private key and once with the remailers. Then only the remailer could decrypt the real recipient's email address and forward it on, without reading the actual message.

          Of course the remailer was vulnerable to surveillance but you could always chain a few of the better ones together. It won't be impossible to trace but it will break PRISM.

        • by Charliemopps (1157495) on Wednesday June 12, 2013 @01:12PM (#43987633)

          But the NSA says it's just collecting the metadata on communications, not the actual communications. So while encrypting the message in your email may prevent them from (easily) reading your email, they still see that you sent or received an email and who it was coming or going to.

          You're forgetting: They are lying. They lied before each leak, and after were proven liers. Now they claim to have told congress "The least untruthful" thing they could. You think they are finally telling the truth now? lol

        • by lister king of smeg (2481612) on Wednesday June 12, 2013 @01:14PM (#43987673)

          But the NSA says it's just collecting the metadata on communications, not the actual communications. So while encrypting the message in your email may prevent them from (easily) reading your email, they still see that you sent or received an email and who it was coming or going to.

          enter torbirdy.

          torbirdy is a addon for Thunderbird email client routing all you email through tor. You can also use a tor hidden email service let them try and unravel who is communicating with who then. you can also use tor with pidgen chat client, and pgp encryption all they will get is random noise lost in the tor network. the problem is trying to get the muggles to bother to use/learn these.

          as it stands today we have all of the technology needed to make prism virtually useless for anything, the problem is the general populous overwhelming apathy and lack of interest as long as they can play stupid facebook games. As long as most the average joe doesn't care enough to act we all are vulnerable we have to communicate at the lowest common denominator. i would love to move all of my communication to double public key encrypted obfuscated triple proxied tor hidden service hosted secure goodness, but grandma can barely handle facebook. so we are all stuck with cc'ing everything to nsa/cia/fbi/homeland.

      • by snadrus (930168) on Wednesday June 12, 2013 @05:00PM (#43990111) Homepage Journal

        This is how Lotus has worked for 20 years. Your log-in key is a file which is your public/private key and public keys of important servers (home server, various "main servers", adjacent domain servers). Then it's PGP all the way down. It's a simple menu option (often force-enabled by your admin) to have your client encrypt the message decryption key for each destination user.

        That's why their webmail requires that you upload the log-in key. And it expires according to your company password policy. The cert trust chain corresponds to the organization's servers, and cannot be spoofed without having the organization's keyfile (on admin server) or using the admin server itself (which is highly logged). This makes the encryption very tamper-proof (in 20 years I've never heard of it broken, and I'd know).

        But this is for organizations running Lotus internal and the organizations it peers with. AFAIK There's no direct + easy standard that does the same thing.

    • by GameboyRMH (1153867) <gameboyrmh@gmail. c o m> on Wednesday June 12, 2013 @12:39PM (#43987139) Journal

      This. Servers you control, communicating using strong encryption set up by yourself alone.

      And even this assumes that the NSA doesn't secretly have any cracks for any strong encryption algorithms. Rumor is they've found a way to efficiently brute-force low-level AES.

      • by LordLimecat (1103839) on Wednesday June 12, 2013 @01:40PM (#43988011)

        Rumor is they've found a way to efficiently brute-force low-level AES.

        A rumor that hasnt been substantiated even after over a decade of analysis by top crypto experts around the world. Color me skeptical.

        Im sure the NSA is good, but AES security has been pretty thoroughly tested, hammered, and inspected for chinks.

      • This. Servers you control, communicating using strong encryption set up by yourself alone.

        And never used for any purpose but converting electricity to heat... because once you hook them up to the wider world (even just to a monitor), you're compromised. (Traffic analysis, emissions analysis, etc... which most 'geeks' seem blithely unaware of, being at least as useful as actually reading the data.*) Seriously, it's a trade off - protecting data that nobody but you gives a fuck about anyhow, or actually using that data to accomplish something useful.

        * Cryptography is fashionable among geeks, it's a cheap way to tighten the tinfoil, but it's only one small corner of information security. Go ahead and feel protected because your head is under the bed - but you should be aware that your ass is hanging out.

    • And of course never communicate with your parents since it's highly unlikely they'll be capable of following the same protocols :)
    • Also, you can hide your metadata through DC-Nets [wikipedia.org]. For the technically minded, Herbivore [cornell.edu] describes a protocol that is highly resistant to attack and provides provable anonymity and secure transmission.
  • by Synerg1y (2169962) on Wednesday June 12, 2013 @11:57AM (#43986403)

    1. Use an email provider nobody's heard about.
    2. Keep social network data private, more importantly don't post anything sensitive.
    3. Don't engage in terrorism, they really hate that.
    4. Somewhere between "get off Windows" and use a live disk, I don't think any OS is truly secure.
    5. Don't save anything locally, keep your accounts hidden, no email notifications.

    Wave at the black SUV outside your window as not having any traceable data may warrant suspicion in itself.

    Move to SA (either one).

    • by AthanasiusKircher (1333179) on Wednesday June 12, 2013 @12:32PM (#43987005)

      2. Keep social network data private, more importantly don't post anything sensitive.

      Are you serious? How about "don't participate in an online social network"?

      Just knowing your set of friends or contacts is enough to extrapolate a huge amount of information about you. So, even if the ONLY data you provide a social network is your friends, that's already a LOT of information.

      The classic study on this was probably about five years ago now, where someone showed how it was possible to predict (to a reasonably high degree of certainty) whether you were gay or not using just your list of friends.

      More recently, it's been shown how easy it is to guess Social Security numbers -- for people of certain ages -- with just things like a birthplace (often same as home town) and approximate birth date, which can often be extrapolated just from a friend list. ("He's friends with a bunch of people all from the same town, and they're all about the same age -- probably high school friends, therefore....")

      Of course, the NSA probably can figure out your SS#, birthdate, birthplace, and similar information without going to any trouble. But the point is that you can often be significantly profiled on a social network even if you never post anything and only accept friend requests from people you know.

      • by DrVomact (726065) on Wednesday June 12, 2013 @06:25PM (#43990861) Journal

        Of course, the NSA probably can figure out your SS#, birthdate, birthplace, and similar information without going to any trouble. But the point is that you can often be significantly profiled on a social network even if you never post anything and only accept friend requests from people you know.

        The NSA can have anything it wants. First of all, they are not in the habit of asking permission, and they simply don't tell anyone what they are doing. Second, there have been perfectly legal ways for the government to buy your data for as long as marketing data has been kept and sold. It's perfectly legal for a private corp to buy your purchase history (via a credit card), the data that Google has mined out of your "free" email service, your transactions with any vendor who has a low integrity threshold (who doesn't?) So what keeps the government from buying it also? Nothing at all. If I were doing it, I'd set up a front corporation (like "Air America" of CIA fame) to buy the data so I don't get screaming headlines.

        The reason for all the hyperventilation is that three things have happened: agencies who lack the subtlety of NSA have gotten into the market, and they've done it directly—that is, they've outright seized the data instead of using the kinder gentler approach of greasing corporate palms. Third, the amount of data they have sucked has gotten so huge that it is impossible to manage without an army of low-level clerks. This is why an Army private and a contracted data massager can give the whole show away. With this many people involved, you are going to have leaks. I am surprised that there have been only two.

        I wonder. In order to fully capitalize on the amount of data they are collecting on us, will it be necessary for all of us to be employed by the US government as DB admins? Welcome to the new Greece.

    • by AmiMoJo (196126) * <mojo@NOspAm.world3.net> on Wednesday June 12, 2013 @12:56PM (#43987397) Homepage

      3. Don't engage in terrorism, they really hate that.

      Problem is that if they dislike you for some reason they tend to define whatever you do as terrorism. Even if you just happen to get blown up by a random drone strike while attending your friend's wedding you become a terrorist.

  • by Anonymous Coward on Wednesday June 12, 2013 @12:01PM (#43986469)

    Just game the system. I've started typing random shit in gmail before I do anything ... let 'em see lots of false positives.

    You know, I'm glad nobody KILLED OBAMA. Durka durka, mohammed jihad. Monsanto sucks. Bush was a simpleton. Death to American cheese.

    Gotta go, someone's at the door ...

  • ISTM data should be encrypted *before* it goes to the cloud.

    That has some UI implications (i.e. gmail can't search the bodies of your encrypted emails). But still seems like a better idea to have your email on your client anyway; so why not have the search index there as well.

  • Lol (Score:5, Insightful)

    by lightknight (213164) on Wednesday June 12, 2013 @12:05PM (#43986557) Homepage

    As with all things, assume that your communications are going to be monitored, whether electronic or not. I know, I know, it's not the answer you want; but the truth is...we put innocent people to death. If we are willing to do that, and not tear down our societies in an act of grief over the loss of a single innocent life, looking deeply within and without as to how or why we allowed this to happen, and how we can prevent it from ever happening again, then caring about protecting your privacy from the monsters waiting outside your door is the wrong approach. You're fighting Evil himself, and he aims to win by any means; if putting a gun to the head of one your children's heads to get you to decrypt your hard drive is what it takes, then he will do it, no hesitation.

  • Easy (Score:5, Funny)

    by Sparticus789 (2625955) on Wednesday June 12, 2013 @12:08PM (#43986597) Journal

    Live in a cabin in the mountains that is over 100 miles from the nearest cell phone tower. Also ensure that you have top cover so satellite surveillance cannot see your house. Add enough insulating material (dirt would be easiest) above your cabin so that there is little/no thermal footprint. And never leave your new found cabin, since cars and feet all leave tracks.

    • Re:Easy (Score:5, Funny)

      by Black Parrot (19622) on Wednesday June 12, 2013 @12:24PM (#43986853)

      Live in a cabin in the mountains that is over 100 miles from the nearest cell phone tower. Also ensure that you have top cover so satellite surveillance cannot see your house. Add enough insulating material (dirt would be easiest) above your cabin so that there is little/no thermal footprint. And never leave your new found cabin, since cars and feet all leave tracks.

      I cover my footprints with aluminum foil, so the satellites and drones can't spot them.

  • by mr100percent (57156) on Wednesday June 12, 2013 @12:10PM (#43986635) Homepage Journal

    PGP. It's good enough for WikiLeaks and Edward Snowden and good enough for me

  • by magic maverick (2615475) on Wednesday June 12, 2013 @12:12PM (#43986671) Homepage Journal

    The solution is encrypt everything (OpenPGP for emails, etc.), plus decentralization. If everyone either hosted their own email, or used a minor hosting company, then it would be much more difficult for the NSA to round up all those emails. Then, if even half the population used OpenPGP for emails, we could hide in the mass, and the NSA etc. will have no hope of reading all those emails.

    As soon as you have just a few spots (e.g. FarceBook, Google-, Murdoch'sSpace) that host the significant majority of a certain type of communication, then you have a huge weak spot. Solution is decentralization and federation.

    Use tools like Diaspora, StatusNet, Jabber, SIP, and email. Don't use tools like Skype, Yahoo Messenger, AIM, Facebook, etc.

    See also: http://autonomo.us/ [autonomo.us] and particularly Reducing vulnerability to massive spying with free network services? [autonomo.us]

  • by Capt.DrumkenBum (1173011) on Wednesday June 12, 2013 @12:13PM (#43986691)
    This is the kind of crap that was held up as examples of why communist countries were so much worse than the US.
    People, the government is supposed to work for you, not the other way around.
    • by Black Parrot (19622) on Wednesday June 12, 2013 @12:30PM (#43986957)

      This is the kind of crap that was held up as examples of why communist countries were so much worse than the US.

      People, the government is supposed to work for you, not the other way around.

      How many times in the last 12 years have you heard "the President's job is to keep us safe"?

      How many times in the last 12 years have you heard "the President's job is to keep us free"?

      Most people vote for low taxes, baseball stadiums, security theater, and enforcing their values on everyone else. Freedom and privacy get trumped by too many of those things.

    • Re: (Score:3, Insightful)

      by SiliconSeraph (996818)
      They shouldn't just be working for you, they should be actively afraid of you. That's what keeps democracy going.
  • by Dputiger (561114) on Wednesday June 12, 2013 @12:15PM (#43986723)

    The problem with heavily encrypted solutions is that they rely on human perfection. There was a story a few months back about Sabu. He eluded the FBI for months until, in a hotel room, he made the mistake of logging into IRC without using Tor first.

    That was all it took. One non-Tor login, and the FBI had him.

    Human beings are not designed for constant watchfulness. We make mistakes. We screw up. Even if *you* stay perfect, the person or persons you're communicating with may not, and if the FBI or NSA wants the details of what you're talking about, they can "break" the encryption at either end of the conversation. Maybe they can't find you -- but if they find the people you're talking to, they can still grab the info.

    I'm not saying that all security is useless, or that there's no benefit to raising the bar. My point is that the solution to this is to *stop spying.* Because, in the long run, almost everyone screws up.

    • by meta-monkey (321000) on Wednesday June 12, 2013 @12:38PM (#43987121) Journal

      Exactly. We weren't secure in our homes because we had unbreakdownable doors, and we weren't secure in our papers because papercuts were too ouchy. We were secure(ish) because the constitution forbade the government from spying on us, and those who did so would be...I don't know, embarrassed?

      Now that's not the case. It's not secret spying anymore. It's routine, obvious, and "perfectly legal!"

      And worse, the storing. The perpetual storage. Never forgetting, always searchable. What you say today innocently will hang you tomorrow (and justly and legally at that!).

      CNN is making jokes by writing about the "Obama reads your email" meme. I wish Obama just read my email. It's boring. But it's not Obama reading my email that kept me awake last night. It was the endless rows of computers, parsing, sifting, correlating, profiling, and storing, forever. And with every record they can "buy" from every corporation.

      But at least they can't read my physical, printed papers without a warrant, eh? I feel so secure. Thanks, National Security Administration. You've done your job well, and a grateful nation salu^H^H^H^Hbows to you.

  • by j1976 (618621) on Wednesday June 12, 2013 @12:22PM (#43986821)

    So, in an effort to hide from NSA you go all out HTTPS. However, to avoid getting those pesky "this site is dangerous!!!" messages browsers show you on self-signed certificates, you buy your keys from any of the larger certificate authorities. Safe? Sorry, no. Almost all those CAs work under American jurisdiction, or on delegation from American CAs. Assuming NSA doesn't get the keys in other ways, all they have to do to get them is to ask the CA and the company would have to hand them over.

    With those private keys available they can listen in on the HTTPS conversations in real time, and there is no way for the participants of the conversation to know this.

    Amusingly enough, the safest bid (well, to hide from NSA at least) would be to use self-signed keys despite all the browser warnings.

    If you still want to get valid keys, here is an interesting discussion [riseup.net] on which CA to choose.

    • Re: (Score:3, Informative)

      by Anonymous Coward

      You don't understand how PKI / X.509 works.

      The CA signs the public key. The private key is not shared with the CA, the CA is not able to decrypt messages. The NSA, potentially having access to the CA's private keys, cannot simply decrypt your messages.

      The NSA could very likely have their own "approved" signing key or copies of legitimate signing keys for which they could launch a man-in-the-middle attack and present their own privately generated version of a certificate and proxy requests to the original si

  • Twitter (Score:4, Funny)

    by ThatsNotPudding (1045640) on Wednesday June 12, 2013 @12:27PM (#43986895)
    I only use one time pads when tweeting.


    ...puts a crimp in the number of followers though.
  • by holophrastic (221104) on Wednesday June 12, 2013 @12:29PM (#43986943)

    So let me get this straight. You've got a military that spends trillions of dollars. You've got eight national defence organizations screwing with your own citizens. And a) you think that you can dodge an organization that has spent that many dollars purely to find you, and b) you think that you don't have a cultural problem?

    Where do you think all of those funds come from? For every tax dollar that you spend, how much goes to military, para-military, and anti-crime organizations? How much of it winds up in actual crime? Are you spending more on anti-crime than you would on crime in the first place?

    Maybe you should solve the actual problem. Maybe you should start electing officials who spend your money on things that you like, instead of things that you dislike. I can't vote for you.

    And correct me if I'm wrong -- you see, my country earned its independence by asking nicely -- doesn't your country believe in violently fighting your own government to break free of restrictions to your freedoms? Have you forgotten how to do that? Your right to fight would seem to be the only freedom for which you do fight, and then you don't use that right to protect your other freedoms.

    One of these days, you'll wake up to realize that you've kept the right, but eliminated the opportunity. What good is the right to bear arms when you can't get away with using it?

    • by EvilSS (557649) on Wednesday June 12, 2013 @01:28PM (#43987879)
      I think the problem, and I find this truly astonishing, is most people here don't seem to care! The only reason to keep the items recently leaked secret is to prevent public outcry over them. Same with classifying the numbers for these programs. Any terrorist smarter than a bag of rocks would have already assumed that we have the capabilities that we found out about last week. They are not that big of a stretch to imagine.

      My fear is now that it's out and the majority of people either don't care or outright support it, we have reset their expectation of what people will go along with and, thus, what they can get away with in secret.
  • This is Stupid (Score:5, Interesting)

    by Rob Riggs (6418) on Wednesday June 12, 2013 @12:50PM (#43987307) Homepage Journal

    None of those things will help you. To the NSA, the content of your email may be less important than with whom you are communicating. Yes, the care about the content of some emails, but their dragnet appears to be for network analysis -- sender, recipients, date, time, etc. The NSA almost certainly catalogs every DNS lookup you do. This is the stuff that is erroneously being referred to as metadata.

    One possibly surprising way to keep your communications private is to read/post your communications to a very public forum. That way the intended recipient is difficult to determine. Keep the communication slightly covert -- a little steganography goes a long way if you can fly under the radar. Just don't trust others with your privacy.

    Our rights are inalienable -- but only if we use them.

  • by backslashdot (95548) on Wednesday June 12, 2013 @12:51PM (#43987319)

    We need a campaign to turn off http. Only https should be allowed, websites should be discouraged from allowing http access. Browser makers should help too, but having popups whenever someone goes to an http site.

  • by Anonymous Coward on Wednesday June 12, 2013 @12:56PM (#43987387)

    Certificate-based encryption (like HTTPS) is only as secure as the certificates that sign sub-certs. If you accept certificates signed by a trusted CA, and that CA is compromised (i.e. controlled or accessible by the NSA, which all of them are), then you have no privacy, and all of your communications can be monitored without your knowledge or consent.

    Here's a good writeup on how it works:

    http://theorylunch.wordpress.com/2013/01/24/ca-mitm/ [wordpress.com]

  • Would take effort (Score:4, Informative)

    by FuzzNugget (2840687) on Wednesday June 12, 2013 @01:08PM (#43987575)

    You could...

    Host your own mail server. Of course, you'd probably have to upgrade your internet service to a tier where incoming mail ports aren't blocked. You'd also need to have SSL/TLS support, ensure everyone whom you email hosts their mail on your server and that you can personally trust them. Not exactly practical.

    Instead of Skype, use a decentralized chat system like RetroShare. Takes some doing to trade PGP keys with friends, but works.

    Use an encrypted proxy for all of your surfing. Practical and quite easy.

    Use encrypted SIP for VoIP communications. No idea how easy or difficult this is, haven't researched it.

    Throw away your landline and cell phone. Goodbye 911 service.

    The point is that the middlemen have proven themselves unworthy of our trust and we should seek to avoid them. The larger and more daunting point is that this breakdown of trust could ultimately lead to a society's collapse.

  • These root servers root packets to their correct locations....

    So duplicates of these packets can be routed to any other location...

    And analyzed for interesting material and then either saved or dicarded...

    So, no, there's not squat you can do. All internet traffic in the USA, regardless of form or format is theoretically possible to search, analyze and store. There may not be enough capacity to save all of it, but the interesting stuff, I'm sure, is compressed, catalogued and stored.

    Can "interest" be evaded? Probably. Encrypting within .pngs and .jpgs might work. Simple agreed upon coding systems in plain text might evade detection. Zipped and encrypted files, I expect, would all be saved for later processing.

    Would allusion packed Klingon poetry get through? Navajo? Elvish? Hard to say. You'd probably take up someone's time though. Keyword flooding might work to overload the filters, but it's hard to say how much capacity is involved. Flooding might not work.

    Partial separated messages would also probably work if there were no obvious semantic or other identifiable similarity. Tricky as well.

    This is just off the top of my head. There are undoubtedly more effective ways to use internet communication in an invisible way, which unfortunately leads me to the conclusion that this effort is going to be fairly effective at catching stupid people and lax people, but not people who are either sufficiently bright, or sufficiently paranoid.

    It obviously also doesn't have a lot of predictive power, otherwise two pseudo-Islamic nutjobs in Boston would have been stopped before they bought their first pressure cooker.

  • by carp3_noct3m (1185697) <`slashdot' `at' `warriors-shade.net'> on Wednesday June 12, 2013 @02:42PM (#43988653)

    I've been meaning for a while to write a guide for friends/family about this. I thing that first you really have to have an understanding of why this is happening, what the goals (hidden and obvious) are for those engaging in the spying, and determine where you stand on the subject before you can't make any sort of plan for implementing the level of privacy you desire. From there the entire discussion is about capabilities and methods. I will forgo the first points in the hope that the hacker mentality still thrives at least somewhat on /.

    First, there was metadata,

    Metadata combined with modern algorithms and big data can give it's owner just about everything on you. Here is what I consider metadata
    (this assumes every point compromised except local, imagine NSL's etc)
    IP - Your ISP will always know this. Circumvention includes tor, i2p, other anonymizing technologies. VPN does not secure your metadata. Wardriving. Rooted boxes.
    MAC - Much less of an issue, can be spoofed easily. Usually not know outside of edge network devices or ISP.
    Time - Heavily used but not well understood. Correlation of login times to compromised activity elsewhere holds up pretty good in court. The longer they've been watching you, the more dangerous to security this is.
    Other machine identifiers (agent strings, cookies, DNS, etc) - mostly a software (and knowledge) issue. Have to be able to prevent DNS leakage, spoof agent strings, keep machine clean of cookies (including harder to find/remove cookie types like flash) If you are on windows... this is your most likely failure point.

    Then, there was low hanging fruit.
    Low hanging fruit: cloud services (webmail providers, social networking, cloud apps, cloud storage/computing, voip/txt chat protocols, etc) If you use these services you must expect them to be compromised and not private. You can choose to not use these services, or compartmentalize use of them (which is my preferred method). Data poisoning becomes more relevant here. Now, you can attempt to be anonymous while using them (say tails(tor) for facebook), but the data is still compromised. But if they can't tie my identity to X, why does it matter. Two reasons: one, because if you are using a service like that, all it takes is one slip up to tie everything to you, and two, because there are other ways beyond even time-data correlation to do so (writing analysis for example)

    So, assuming you have figured out how to be relatively anonymous and encrypt your data (ssh, tcplay, dm-crypt, gpg) You self host as many services as possible, and directly connect to people/sites you "trust". You have in intelligence terms "gone dark" or "dropped off". I'm going to ignore the issue of DPI for the moment.

    This is where the majority of people who care about privacy want to be. They want to be just enough of a hard target that it's not easy to grab up their info. This is what the 90's cryptowars were about. The ability to go dark.

    The problem with this state is twofold: First, your data can still be retroactively inspected. So that AES-256 you think is nice and secure is finally cracked by the NSA (if it isn't already). Then they run it on gobbled up data from the past, and suddenly your encryption is worth jack. (save discussion of storage feasibility for another time, some of the math has already been done over on Schneiers blog)

    Second, once you become a target for other reasons, they will resort to other methods. First with off-site but close compromise. Usually ISP. Then escalated to remote compromise (trojans, keyloggers, etc through 0-days or backdoors) If for some reason you are still safe at this point, commence black bag operation. While you are at work, they break into your house and plant a physical keylogger, audio bug, copy HDD, install trojan (MBR not encrypted? evil maid!) or any other number of growing possibilities. This boils down to your physical security. Think your ADT alarm system works? Think again (well, this depends on who you pissed off, normal

One possible reason that things aren't going according to plan is that there never was a plan in the first place.

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