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Security

How Would You Prefer To Send Sensitive Data? 542

sprkltgr writes "Our HR department is implementing new software. The HR Director has tasked me with sending our data out of our network to the consultant that's loading it in to the new package. Obviously this data includes items such as SSN, name, birth date, etc. Upon being told that I would not email this data to her, the consultant asked what my security requirements were for sending the data. What would be on your wishlist for the best way to send sensitive data to someone outside your firewall?"
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How Would You Prefer To Send Sensitive Data?

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  • PGP (Score:5, Insightful)

    by Foldarn ( 1152051 ) on Wednesday May 21, 2008 @10:31PM (#23500152)
    PGP without pause
  • by Orange Crush ( 934731 ) * on Wednesday May 21, 2008 @10:32PM (#23500170)
    Not at all if I could avoid it, that's for sure. Why can't the consultant import the data into the new package on-site? Even the most secure transmission method can't stop someone outside of your control exposing that data. I'd be talking to my HR people and begging them not to send this data out. Probably a good idea to talk to Legal too.
  • by rboatright ( 629657 ) on Wednesday May 21, 2008 @10:38PM (#23500206)
    unless the data set is so large that the answer is pgp on an external hard drive shipped by fedex. and send the password by a SEPERATE CHANNEL. I prefer to send the key by TELEPHONE -- spoken, but that's up to you.
  • Locally (Score:4, Insightful)

    by thedarknite ( 1031380 ) on Wednesday May 21, 2008 @10:38PM (#23500208) Homepage
    I'd get the consultant to come to the office. If the new software is going to be run onsite, there should be no reason why the data needs to leave. But if it does need to be taken offsite then having the consultant come in to collect it makes them responsible for keeping the data secure.
  • by RKThoadan ( 89437 ) on Wednesday May 21, 2008 @10:41PM (#23500252)
    While its generally true that the public key should be public, the issue then becomes just how do you know whose public key you are getting? You should attempt to authenticate that the key you have is indeed their key.
  • by RickRussellTX ( 755670 ) on Wednesday May 21, 2008 @10:46PM (#23500288)

    Simply use symmetric encryption (AES-256, for example) with a strong random key, then provide the key on a separate hand-delivered or voice-delivered medium.

    Public key doesn't really buy you anything in this case -- if somebody grabs their copy of the symmetric key, you're screwed. If somebody grabs their copy of the private key, you're screwed. Protecting the private key with an additional symmetric key doesn't make it more secure.

    But explaining to a clueless consultant how to keep a single key secure is a lot easier than trying to explain public key/private key operation.

  • Pinkerton (Score:5, Insightful)

    by tverbeek ( 457094 ) on Wednesday May 21, 2008 @10:50PM (#23500304) Homepage
    Hand delivered by a trustworthy courier.
  • by Tex2000 ( 26062 ) on Wednesday May 21, 2008 @10:52PM (#23500324)

    The policy in my current company is that NO DATA is shared unless we have a "Non Disclosure Agreement" (NDA) Signed with the company/consultant that needs to work with our data. Have your legal department prepare such an agreement with items such as penalties for improper use of the information..

    This kind of agreement sometimes scare consultants or companies, and it's cause for some struggle, but in the end if they can't handle the responsibility over your data then you should find someone who can.
  • by NeverVotedBush ( 1041088 ) on Wednesday May 21, 2008 @10:53PM (#23500334)
    I agree completely with Orange Crush. You let that data out and it is now subject to this other entity's security policy.

    If you are going to let it off-site, is there a contractual agreement regarding how the data will be protected? Are their security policies audited by a third party? Worst case, does your company's insurance cover financial losses due to a third party mishandling your data?

    I'd provide them with dummy data in the proper format to simulate your company's data and do like Orange Crush suggests and put data and application together only on your own premises.

    But if you can't/won't do that, I'd say encrypt the hell out of it and burn it to CD, and send it by registered courier where someone has to sign for it to acknowledge chain of custody. Send the key by an alternate method.

    Do you know this company's security policies? Are there any kind of investigations/background checks performed on its employees? If it is a small shop, what kind of firewall protection do they use? Is some programmer's kid using his laptop to play games on the Internet and download "free" screen savers or ring tones?

    I assume that your data is in there too. How would you want it handled and what would you consider doing legally to your company if the data was in any way mishandled and your information to find its way into some identity thief's possession or posted on the web? What if your identity were to be stolen and your accounts raided or your credit ruined?

    I know this probably sounds fairly paranoid and I'm sure a lot of people might suggest easier and less secure approaches, but the reality is that this kind of data is a target and far too many people do not properly protect their business computer systems because they just don't realize how pervasive intrusions and spyware are.

    How would you want your data handled?
  • by Geek_engineer ( 1293668 ) on Wednesday May 21, 2008 @10:56PM (#23500358)
    I would be much more worried about the security after you get the data there. How does the consultant protect his network (wireless???) and physical building? Does he keep the data encrypted so if a computer is stolen, it cannot be read? There are any number of good encryption methods to use in transmitting the data, then phone with the key.
  • by Alpha830RulZ ( 939527 ) on Wednesday May 21, 2008 @10:58PM (#23500370)
    If it were me, I wouldn't even be worried about FTP for a one time transfer. When was the last time , or the first time, you heard of someone sniffing sensitive data in mid transmission? The vast majority of compromise issues are due to compromise of files on a machine somewhere. You should be concerned about the work environment of the consultant, and procedures there, far more than how you get data to the consultant. Ad hoc work environments are usually far more lax in their controls than a production environment. HR departments are (in my experience) far less knowledgeable about how to protect data than IT types. This is where your risk lies.

    We use an SFTP server for transmission of financial data, and I don't lose a bit of sleep over it. You are at much higher risk for either your HR department or the consultant doing something stupid with the source or result files on their network. Your need is just to make sure that it doesn't happen on your watch.

    I would be more concerned about making sure that the HR folks and the consultant cleaned up their work files afterword.
  • Secure in layers (Score:5, Insightful)

    by sthomas ( 132075 ) on Wednesday May 21, 2008 @11:01PM (#23500390)
    If you are required to transfer the data outside of your organization, then there are two areas of concern - confidentiality of the data in transit, and confidentiality of the data once it arrives and is in the consultant's control.

    Data in transit:
    Encrypting the data prior to transfer is highly recommended, so that when it arrives it is in a secured package, and it also reduces risk should an email be misaddressed or forwarded to an unintended recipient. For this part PGP is an excellent tool. You can encrypt using exchanged keys, or you can encrypt using a strong passphrase and then communicate that passphrase out of band (phone call is preferable, separate email is workable but less preferable). For the method of transfer, securing the channel of communications is another added layer of security on top of encrypting the data ahead of time. If you are using an interactive transfer like (S)FTP, it will protect the authentication credentials from prying eyes. Although someone intercepting the PGP encrypted file now may not be able to decrypt it, tomorrow's technology may make the task trivial, so protecting it is recommended. TLS-encrypted email from organization to organization is also a good choice, but may be beyond the scope of your project. However, if this will be an ongoing need, or if your HR rep is also passing confidential content in email, it's definitely worth looking into.

    Data Protection after Transit:
    Once the person has received the file, your data will continue to be at risk. Each copy they make of the encrypted file is another file that could potentially be moved outside of a controlled environment. Once they decrypt the data, the risk to your organization climbs as they strip away another layer of protection. At this point the processes the consultant has in place are critical to protecting your data, and lack of processes or sloppy adherence puts your organization at risk. I often use users' Outlook Sent Items to show how easily copies of data files propagate. Anywhere they store the data, encrypted or not, may be released outside of their environment when they dispose of hard disks or tapes, or if they have them replaced because they are faulty. We empower users with tools, and those tools can increase risk in unexpected ways.

    Remember the most important security rule - always protect in layers. Remind everyone to treat all data like it's their own banking information or cash money. Require your partners/vendors/consultants to meet or exceed all of your controls. Allow as few copies of data (encrypted or non-) as absolutely required for operational and preservation purposes. Continually remind everyone of the potential risk of data loss. Make sure users understand that there is no single security solution - encryption provides one layer of protection, but the best security is constant vigilance and treating your data like it's cash money.

    I would recommend you have a serious discussion with your HR rep, starting out by saying "I just want to be sure you're aware of the risk here, and we are doing everything we can to protect our company and our employees." Then spell out the risks without exaggerating, and remind him/her that it's situations like this where bad decisions end up in the newspaper. The first decision is "do we have to move this data outside of our organization?" and it should only be done if it's absolutely required. If it is, then layering security and requiring that your vendor/contractor treat it with the right level of sensitivity are all that you can do.
  • Re:PGP (Score:5, Insightful)

    by Swampash ( 1131503 ) on Wednesday May 21, 2008 @11:01PM (#23500392)
    If this is for a work task (and in the parent article it obviously is) I would only ever send sensitive data via PGP-encrypted and -signed email, or more specifically via PGP-encrypted and -signed attachment to an email.

    Via encrypted signed email there's a paper trail. "The data you have is verifiably the data that I intended for you to receive, and the sensitive data haven't been mangled or modified (the hashes match), it is verifiably from me (that's my signature), and I have demonstrably met your request by sending you the information on this day at this time (email headers, server logs, whatever).

    If it's important and it's for work purposes, COVER ASS AT ALL TIMES.

     
  • by Swampash ( 1131503 ) on Wednesday May 21, 2008 @11:06PM (#23500432)
    I would be much more worried about the security after you get the data there.

    Speaking as if I was the poster of the original question, I don't care what happens to the security after I get the data there. It's not my problem.
  • by NeverVotedBush ( 1041088 ) on Wednesday May 21, 2008 @11:10PM (#23500472)
    There are a lot of good posts in this topic. Especially the ones about the legal issues.

    These days a big issue is CYA when it comes to people's personal data. As others have noted, be sure to investigate any laws that might define how the data must be treated if it has to go off site. Be sure that your management signs off on the procedure and be sure you can document it.

    The days of just letting people download data are long gone. And don't use FTP if you do. Use the secure version (sftp) and encrypt the data before it transfers. That way it's an encrypted tunnel carrying encrypted data. But I wouldn't recommend this method. I'd get a signed chain of custody with media physically delivered and assurances that all copies of the data is completely and securely destroyed and the original media returned when the job is finished.

    Best way is not to let the data out in the first place.
  • I agree completely - getting the files TO the consultant securely is relatively easy... a GPGP key exchange followed by a phone call can pretty simply ensure who they are as well as anything. (I mean, as well as you know who the company is now - it's whoever answers their phone number.)

    But then they HAVE the data, and if you care about your data, that's a problem.

    In a perfect world, I would start by finding a new consultant - one who wouldn't even consider RECEIVING such data through email. I suppose in a PERFECT world, there wouldn't BE such consultants.

    But failing that you need to lay out every security policy you think is important to secure your data, including INSIDE a network... firewalls, care with files, background checks on IT staff, background checks on the consultants. You need this laid out in excruciating detail. And you need it in the contract with them.

    Ideally YOUR company needs to do the background checks on their staff... At a minimum you need to do a really sound credit check of them and have your attorney draw up a contract where they indemnify you for any loss due to a breach and any attorney fees to defend against and to recover from it. Etc.

    Basically the same kind of due diligence you'd have for someone you were letting come in and install new servers and new firewalls on your site with access to everything you've already got. Or if they refuse to get up to a reasonable standard, you can tell them they need to do their work on your site.

  • Re:PGP (Score:5, Insightful)

    by Metzli ( 184903 ) on Wednesday May 21, 2008 @11:15PM (#23500514)
    I would agree with PGP, once the proper legalities and assurances are in place. However, I'd worry about the non-technical issues before working on a technical solution.

    There are a number of issues to be resolved before worrying about how to get the data transferred. Has the consultant and/or their firm verified their security and controls to your firm's satisfaction with something like a SAS 70? Are there legal agreements in place concerning the proper controls of this data, the explanations or responsibilities in case of a disclosure, etc.? Has the idea been proposed to create bogus data for testing so that live data isn't used? Can the application be loaded on-site, so that a machine outside of your firm's control will not contain highly-sensitive employee data?

    I'd ask a lot of questions like these and get answers to my satisfaction before I sent out any data. I would greatly prefer to have to explain to my management why I'm "holding up the train" than have to explain to my coworkers why I was involved in the disclosure of their personal information and mine.
  • Red flag. (Score:5, Insightful)

    by PeanutButterBreath ( 1224570 ) on Wednesday May 21, 2008 @11:19PM (#23500538)
    If this consultant asked for this data to be sent via email in the first place, that is a big red flag to me. It suggests a pretty lax attitude towards sensitive data, possibly an indication of general cluelessness/laziness/hubris.

    Frankly, I would be a little suspicious of any person who wanted to take custody of this information at all if test data can be used instead. I would never take on that kind of liability if I didn't absolutely have to.

    In an environment where neither HR nor their contractor seem to have a clue, I would enumerate my concerns (in writing) and insist that they make the call (in writing). Too many weak links in this chain.
  • Re:PGP (Score:5, Insightful)

    by shri ( 17709 ) <.moc.liamg. .ta. .cmarirhs.> on Wednesday May 21, 2008 @11:27PM (#23500588) Homepage
    I disagree. While PGP can transport the data securely, once decrypted, it will be rendered as insecure as the consultant's weakest point of security. If the data were truly sensitive, I'd send an anonymous set to the consultant, have them prepare a set of scripts / routines / procedures to import and then bring them onsite to complete the task.
  • Physical transport (Score:2, Insightful)

    by Anonymous Coward on Wednesday May 21, 2008 @11:32PM (#23500610)
    In the hands of a bonded, insured, courier, into the hands of someone under a very draconian contract that spells out in a very big way what will happen to them if even a single record is leaked.

    Seriously, this is not something you want to ever push across a network that has untrusted eyes anywhere, no matter what your encryption policy. Heck, you need to keep your own employees away from it even on the local network.

    If the contractor is going to be putting it into new software that will run at your site, you need to bring the contractor into your facility to put the data in directly.

    If the contractor is still developing the software, then the contractor doesn't get a single row of real data.

    If the software runs somewhere else, you had better make sure that all appropriate measures are in place to safeguard the data, and you had better be REALLY sure that this offsite solution is the best option.

    Once you let even a teeny tiny bit of this data out where someone can take it, you're in for a world of hurt.
  • Registered Mail (Score:4, Insightful)

    by john.r.strohm ( 586791 ) on Wednesday May 21, 2008 @11:37PM (#23500638)
    I'd send it on CDs, by Registered Mail, the same way defense contractors and government agencies send classified stuff, for the same reasons.

    Yes, Registered Mail costs more. It is worth it. Registered Mail *EXISTS* for the sole purpose of shipping high-value items that MUST NOT GET LOST OR STOLEN. That is precisely what you have here.

    And for those of you in the peanut gallery: Yes, I have done Registered Mail. Several times. It is a pain in the ass. The Postal Service thinks it is a pain in the ass, and will try really hard to talk you out of it. I usually have to say "Registered Mail" two or three times before they figure out that I really do know what I want. I have had Postal Service clerks ask if I knew the difference between Registered and Certified. They were always very disappointed when they discovered that I *DID* know the difference, could explain it to them, and wasn't about to back down.

    If you are really paranoid, you send two packages, both by Registered Mail. One contains encrypted CDs. The other contains the decryption key. Or you split the data into two packages, that must be combined in a nonobvious way to reconstitute the data.

    But the KEY to the transfer is Registered Mail.
  • by Jerf ( 17166 ) on Wednesday May 21, 2008 @11:37PM (#23500646) Journal
    If the consultant really expected you to email the data, and expressed even a modicum of surprise that you wouldn't do it, they've already disqualified themselves from being able to securely handle your data.

    Do you really think that this is the only flaw in their handling of sensitive data? That, otherwise, they are security conscious and careful, except for this odd flaw where they don't understand how insecure email is?

    If you care, it's time to change consultants.

    If you don't care, just email it already.

    (I'm actually not quite as rigid as this may sound out-of-context. I don't agree that security is all-or-nothing, so please don't strawman me that way. My second paragraph is important; anyone who expects those things emailed to them is so far away from the necessary knowledge and skills that debating whether they are close enough or whether they will be able to take reasonable care is a waste of time, arguing about whether the receiver made a touchdown when they got tackled on the 10 yard line on the wrong side of the field.)
  • Emailed? (Score:3, Insightful)

    by e-scetic ( 1003976 ) on Wednesday May 21, 2008 @11:51PM (#23500744)
    If I was that consultant my first question would have been how to transfer that data securely - but maybe that's because I know what I'm doing. Therefore, I'd be totally allergic to giving that data to this consultant, regardless of any non-disclosure agreement.
  • What to do (Score:3, Insightful)

    by hejish ( 852589 ) on Wednesday May 21, 2008 @11:54PM (#23500766) Journal
    First, your company must have a policy. SSN's are sensitive data. Second, your company must have a contract with any folks not working for your company requiring that this data be protected in a manner compliant with your company policies. Third, the recommendation to have the consultant work on site or work with the data on site is appropriate. Requiring that the data NOT leave your site sounds very reasonable. If they are remote use 2-factor authentication to get into such sensitive data and administration of systems.
  • by pyite ( 140350 ) on Thursday May 22, 2008 @12:02AM (#23500820)
    The right way to delivery a symmetric keys is using asymmetric key, like RSA. Where no hand delivery is needed and is very secure.

    Uh, only if you have public key infrastructure (i.e. pre-trusted authorities). I can generate shared secrets all day long with Diffie Hellman, but it really only helps me if I know that the recipient is not a man in the middle.

  • Re:Red flag. (Score:3, Insightful)

    by bugg ( 65930 ) on Thursday May 22, 2008 @12:07AM (#23500862) Homepage
    Public key cryptography solved the key exchange problem years ago. Why send keys in the mail?
  • ...by email.

    This consultant wanted you to send it to them? I've been a consultant and developer for nearly 20 years. I would NEVER EVER ask for data like that to be sent to me. I wouldn't want to be anywhere near owning that kind of responsibility for someone else's critical data. You couldn't make me take it if you tried.

    Your biggest problem, as pointed out by others, isn't the in-transit data but rather what it does once the consultant gets it. If he's so unaware of modern security best practices as to ask you to send it to him, it's fairly a sure bet that his environment and practices are no where near good enough.
  • MY GOD!!! (Score:3, Insightful)

    by Jane Q. Public ( 1010737 ) on Thursday May 22, 2008 @12:34AM (#23501022)
    What overkill. People recommending multiple-step, even multiple-encryption, systems. And software that needs installing and configuring on both ends. And so on.

    As long as the file gets there safely, you don't care what they do with it on the other end, right? (That is the most common scenario.)

    So these people are trying to shoot ants with cannons. Massive overkill. REALLY all you need is scp, and unless you are running Windows, it is already built-in and needs little if any configuration. It's ready to fly.

    You would be hard pressed to get better security during transmission, and when it gets to the other end it is in its original form. No messing with keys or pads, no UN-encryption, in fact nothing at all for them to do. Send it via scp and there it is. All you need is for them to give you a username and password, which is a hell of a lot simpler than some of those other ideas.
  • by elronxenu ( 117773 ) on Thursday May 22, 2008 @01:28AM (#23501276) Homepage

    You are about to send sensitive data to a third party who will load it into a new database and send you back the database. That's insane.

    You need to bring the destination (the database) in-house. Either load the data yourself, or get the consultant to come in-house to load the data. Under no circumstances should the sensitive data travel outside your network boundary. It's not a question of "how strong is my encryption" at all.

  • AES 256 (Score:4, Insightful)

    by Heembo ( 916647 ) on Thursday May 22, 2008 @01:34AM (#23501318) Journal
    WinZip with AES 256 encryption using a very strong password delivered via phone is sufficient in some situations.
  • S/Mime (Score:2, Insightful)

    by jonoton ( 804262 ) on Thursday May 22, 2008 @01:56AM (#23501434)
    Funnily enough I've been asked pretty much the same question.

    Slightly different scenario, in this case it's payroll information being sent to the company that deals with the payments.

    The "consultants" suggested emailing it, when I said that wasn't going to happen they suggested putting it on an ftp site. (What the hell are we paying them for?)

    As the people involved at both ends are not IT people and are all on Windows PGP isn't really an option, but S/Mime is. It also gives the advantage that you can say - go buy an email certificate from this website (pointing them at verisign/globalsign/another-t-t-p) and let them worry about the authentication issue.

    S/Mime is integrated into all the common MUA software these days, certainly anything they'll be using on windows, and it's really quite easy to use.

    The downside of it is that the security of the system boils down to key management & users. Once you've told them it's ok to email this information how do you guarantee that it's been sent encrypted?

  • Not by email... (Score:3, Insightful)

    by Secret Rabbit ( 914973 ) on Thursday May 22, 2008 @02:03AM (#23501466) Journal
    ... I what people seem not to get/missed.

    1) Strongly encrypt the data via your favourite method

    2) Setup an Sftp with a user name/strong password for the consultant*

    3) Send the user name/strong password to him/her via email (PGP/GPG)

    4) Keep the login log in a very safe place, along with any other email exchange, keys, etc that show the transfer has occurred and by whom.

    * If you want to have a even better "paper" trail, have them send you the IP of the host that they will be logging in from and limit access to just that host. Also have make sure that this IP is verifiable owned by the consultant firm. Keep the verification.

    If all of the above is done, you have made sure that the login has been done through the only *one* IP allowed (owned by the consultant firm), through a login that only one person has. So, any fuck-ups are there's and there's alone.

    But, if possible, I'd also require them to keep the data encrypted and only decrypted for use, preferable not to a HDD (ram disk). Not to mention any other mechanism that you can think of. Also make sure that the paper work requires any and all requirement to be applicable to any subcontractors as well as any of the subcontractors subcontractors, etc. Because, these consulting firms have a rather poor track record of keeping this data secure. And if they don't do it, and bad things happen, there is legal recourse on your part (as well as possibly the people who's data it is).
  • SneakerNet (Score:1, Insightful)

    by Anonymous Coward on Thursday May 22, 2008 @02:07AM (#23501488)
    Copy the data to a hard disk, carry the hard disk between sites.
  • Re:PGP (Score:5, Insightful)

    by Eivind ( 15695 ) <eivindorama@gmail.com> on Thursday May 22, 2008 @02:36AM (#23501634) Homepage
    The likelihood that "someone" will brute-force the encryption is zero -- or close enough to make no difference. All the worlds banks are protected by the same encryption. If your data is REALLY more valuable than complete access to EVERY account in EVERY bank that has online banking, then you don't "ask slashdot" what to do about securing the data anyways.
  • SFTP, PGP or bust (Score:2, Insightful)

    by StealthyRoid ( 1019620 ) * on Thursday May 22, 2008 @02:50AM (#23501690) Homepage
    I agree with the few posts I've read that've recommended PGP, but there's an easier alternative if you don't want to go through the hassle of setting up PGP keys for non-technical users: SFTP. It runs over SSH, so you're as secure as you would be when logged into a shell, and it doesn't matter which one of you has which side of the connection (client/server, I mean). There are probably some auxiliary benefits to SFTP, like controlling at least one place where the document is stored (as opposed to having it sit on some random company's email server, even in encrypted form), but the ease of use is probably the main reason to use it.

    I'd probably be persuaded that the overall benefit of spreading the use of encrypted and digitally signed email is greater than the effort put into explaining to Suzy Secretary how to install Enigmail.
  • by emj ( 15659 ) on Thursday May 22, 2008 @02:52AM (#23501698) Journal
    You are missing the point, the worst thing that happens to the data is when it arrives to the consultant. These kinds of databases are something everyone sees value in, and makeing a copy is trivial. (Even though the consultants laptop isn't on the network, and not plugged into power)

    Make it very clear that this data can not be exposed. See some good posts:

    http://ask.slashdot.org/comments.pl?sid=560624&cid=23500514 [slashdot.org]
    http://ask.slashdot.org/comments.pl?sid=560624&cid=23500510 [slashdot.org]
    http://ask.slashdot.org/comments.pl?sid=560624&cid=23500324 [slashdot.org]
  • Re:Pinkerton (Score:3, Insightful)

    by jamesh ( 87723 ) on Thursday May 22, 2008 @03:06AM (#23501770)
    Or, if the consultant is somewhere nice, hand delivered in person. "Sorry boss, I don't trust anyone else to deliver this keyring sized memory stick to Hawaii."
  • Re:PGP (Score:3, Insightful)

    by Simon Brooke ( 45012 ) <stillyet@googlemail.com> on Thursday May 22, 2008 @04:48AM (#23502284) Homepage Journal

    has the resources to brute-force the encryption
    If you're using PGP, such resources simply don't exist.

    You are being awfully naive here. Personal details are worth about US$50 each to identity fraud gangs. 10,000 personal details times US$50 is half a million bucks, and that buys a lot of supercomputer time. Any encryption can be brute forced given enough brute force.

  • Re:PGP (Score:5, Insightful)

    by Simon Brooke ( 45012 ) <stillyet@googlemail.com> on Thursday May 22, 2008 @04:48AM (#23502286) Homepage Journal

    VPN *AND* scp? weirdo.

    Not in the least. What guarantee do you have that there isn't an attacker already in your network, or the recipients network? Split into small chunks first. Encrypt with separate keys, then SCP over VPN.

  • by Yvanhoe ( 564877 ) on Thursday May 22, 2008 @05:32AM (#23502488) Journal
    It is of no use to set up a secure channel if the person you are sending to doesn't understand why you would like to secure these data
  • by ocbwilg ( 259828 ) on Thursday May 22, 2008 @06:36AM (#23502750)
    Upon being told that I would not email this data to her, the consultant asked what my security requirements were for sending the data. What would be on your wishlist for the best way to send sensitive data to someone outside your firewall?"

    Your consultant wanted you to email the personal data to them to begin with? Well, first on the wish list would be a new consultant, preferably one who takes security seriously enough to not ask that confidential personal data be sent via email. It's not like they don't know what kind of data they have there, and the lack of consideration for security in acquiring the data from you does not bode well for how it will be handled once they have it. I would probably require that they either come on site and work with the data via your machines on your network, or I would demand a partnership agreement with them that spells out hefty penalties if they fail to follow specified security practices, especially if that failure leads to data compromise.
  • Re:PGP (Score:3, Insightful)

    by eric76 ( 679787 ) on Thursday May 22, 2008 @06:38AM (#23502766)

    Yes. The Russian mafia. They have much more than sufficient resource - not merely access to supercomputers, but also access to large botnets of other people's PCs. Cracking encryption is a task well suited to distributed computing.

    Yes, these people can and routinely do crack military grade encryption, if the data is valuable enough. This data is valuable enough.

    Would you perhaps have some real information to support those claims?

    If they are cracking military grade encryption, which I very seriously doubt, then they are likely doing so by buying the keys from someone, not by brute forcing it.

  • Re:PGP (Score:2, Insightful)

    by silanea ( 1241518 ) on Thursday May 22, 2008 @06:38AM (#23502768)
    Quite a lot of stuff is worth cracking. That does not have any influence on what can be cracked. Computing resources available today are enormous, but they are still finite. And to the best of my understanding they will be quite finite enough to ensure our privacy for the next couple of decades. But since you so vehemently say otherwise, you surely posess reliable and verifiable information to the contrary that you could share with us here to enlighten us?
  • Re:PGP (Score:3, Insightful)

    by xalorous ( 883991 ) on Thursday May 22, 2008 @07:14AM (#23502960) Journal
    Use strong encryption.
    Burn to physical media.
    Send via bonded courier.
    Send password via encrypted email, or via registered mail.

    If you need frequent access from both ends, set up extranet with encrypted vpn with reasonable security on both ends. The data at rest should be encrypted with strong encryption and the password should change frequently ( 90 days). Access to the password and to the storage folder should be restricted.

    Yeah, all you alarmists worried about 'one compromised computer' are right, but that threat exists no matter how you connect to transfer the data. The VPN doesn't answer this threat, it answers the threat of capture of data in transit.
  • Re:PGP (Score:3, Insightful)

    by grommit ( 97148 ) on Thursday May 22, 2008 @07:31AM (#23503064)
    Now you're the one that isn't thinking. Assuming the OP doesn't use an insanely short bit length, it would take EVERY SINGLE COMPUTER ON THE PLANET working together at least a decade to brute force it.

    The math is simple, the amount of computing power to brute force PGP just doesn't exist on this planet yet. Maybe in a decade or two but then all we'd have to do is increase the bit length that PGP uses.
  • Re:PGP (Score:4, Insightful)

    by ezzzD55J ( 697465 ) <slashdot5@scum.org> on Thursday May 22, 2008 @07:35AM (#23503090) Homepage
    Note that an extra bit does not double the effort, it squares it. Do the math.

    What?

    An extra bit does double the keyspace.

  • Re:PGP (Score:3, Insightful)

    by Chris Mattern ( 191822 ) on Thursday May 22, 2008 @08:01AM (#23503248)
    Yes.

    However, it is practical to have a large enough keyspace that "enough brute force" cannot be realistically achieved, even assuming machines millions of times faster than the fastest currently available.
  • Re:PGP (Score:5, Insightful)

    by 0xFCE2 ( 859134 ) on Thursday May 22, 2008 @08:07AM (#23503292)
    Yes. The Russian mafia. They have much more than sufficient resource - not merely access to supercomputers, but also access to large botnets of other people's PCs. Cracking encryption is a task well suited to distributed computing.

    Yes, these people can and routinely do crack military grade encryption, if the data is valuable enough. This data is valuable enough.


    "military grade" is a pretty useless term here - the military uses all kind of encryption, from weak to very secure. But when talking about encryption suitable for "secret" stuff (i.e. classified secret), then you can be pretty sure the NSA is not going to allow any form of encryption which is known (to the NSA) to be breakable. Not breakable by any other (foreign) government agency with a multi-billion-dollar budget, and certainly not by the Russian mafia. And as a reminder, AES is a valid algorithm be used to protect secret communications and available to pretty much everyone.
    To get your data, they would try to get the encryption keys by hacking the computer or by physically breaking into your house and office. They might even sneak backdoors in the software you are using and weaken the encryption artificially. But they will not bother with the encryption itself, unless you've been using weak encryption from the start.
  • by cybercat13 ( 1206016 ) on Thursday May 22, 2008 @08:17AM (#23503350)
    Good point, however, the point needs to go further. Sensitive data should not be electronicaly transimitted without the approval of one management level higher than the requestor. Also, the request should include a signed MOA as to what the data is to be used for and how the data will be handled otherwise the sender of sensitive data can be held liable for the release of the data.
  • by Anonymous Coward on Thursday May 22, 2008 @08:48AM (#23503664)
    Make the consultant come on site and perform the operations on your equipment in your infrastructure.

    If you send it PGP encrypted that only covers you during the transfer. What happens to the data after they unencrypt it? Do you trust them to securely delete it? I don't, not unless it is included in the contract.
  • DVD/hand carried (Score:3, Insightful)

    by klubar ( 591384 ) on Thursday May 22, 2008 @09:15AM (#23504024) Homepage
    Actually if you use USPS registered mail you'll get a traceable route of the data. If the data is super valuable, you can contract with a secured courier (think armored truck) to transport the CD. We occasionally do work for financial services firms, and since they already have a armored truck courier service for moving cash, it's easy for them to schedule a pick up with an armed guard.

    Even if the CD is stolen, it's still encrypted--and armored trucks (especially ones carrying data) are rarely held up--and they have insurance.
  • by HEbGb ( 6544 ) on Thursday May 22, 2008 @09:45AM (#23504398)
    This is really dumb. Just encrypt the file using any number of techniques (sheesh, even WinZip has decent encryption now) and email it. Then call him on the phone with the password.

    This isn't rocket science, folks.
  • Re:PGP (Score:3, Insightful)

    by ezzzD55J ( 697465 ) <slashdot5@scum.org> on Thursday May 22, 2008 @12:20PM (#23506864) Homepage
    It's not a matter of realistic, but a matter of physics that there's a finite number of computations that can be done in the remaining lifetime of the universe, and it's easy to make a key large enough the keyspace can't be searched in it. If you're saying that 'enough brute force' doesn't have to fit in the space and time we have in this universe, then fine.
  • Re:PGP (Score:3, Insightful)

    by MikePikeFL ( 303907 ) on Thursday May 22, 2008 @01:06PM (#23507560)
    FTP still has its place. If you are already going over VPN, FTP can be way better than SMB if say, the link dies at 699MB of a 700MB file. FTP resume performs miracles with an appropriate client (read ncftp). scp/sftp don't regularly support resume (I think there are some hacks out there), and sometimes rsync isn't universal (Win32, permissions, and rsync can do some evil things).

    Obviously it all depends on the platforms in use, the links' reliabilities, the links' speeds, the criticality of time, one's patience, one's pain threshold, etc. YMMV.

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