Encrypt a file so that only a SSL site's private key can decrypt

by bigiain • 15 years ago

55 43 15 years ago

Confusion• 15 years ago

A script without context or explanation of what it is useful for. Why did you submit this?

patio11• 15 years ago

That's a neat hack. I once had call to send banking details to a client. It was very annoying - eventually settled on encrypting an emailed zip file and sending password out of band.

This, on the other hand, turns any web developer's SSL cert into their PGP key without their advance cooperation. (They don't have to have one, understand why they need one, or create one and publish the public key. They just have to have an https site, like all my clients already do.) Limited utility, since decrypting is impossible for regular people and larger corps would have that private key locked down like crazy, but a very neat hack. I could actually see myself using it, too, for secure geek-2-geek transmissions.

k00k• 15 years ago

Friends of mine have created http://lockify.com/ exactly for the purpose you outline with the banking details.

inaequitas• 15 years ago

Zed Shaw wrote this (https://twitter.com/#!/zedshaw/status/54434747652390912) and then him and Dan Kaminski had a good talk on Twitter about it.

zwp• 15 years ago

Great I think that got most of it (validation!) but revocation checking worries me and a skim of the OpenSSL (0.9.8o) sources doesn't leave me with the warm'n'fuzzies.

s_client.c calls SSL_CTX_set_verify() (the default verifier). Results from that can be obtained from SSL_get_verify_result() and are documented in verify(1).

All of the CRL/revocation-related return codes there are marked "unused". There is no mention of OCSP.

I found found a "crl_check/crl_check_all" option for verify(1). Command line help mentions an "ocsphelper". OpenSSL does have a separate OCSP client. But I don't think any of this machinery is activated by default.

bigiain2• 15 years ago

I thought it was a fabulous (tho limited utility) hack around the key distribution problem.

bluppy2• 15 years ago

Since the RSA algorithm for public/private key algorithm can only encrypt payloads as large as the (public)key, this is the only way to safely encrypt files.

That's why PHP provides the openssl_seal function can do exactly the same (and more) as the given code. (http://php.net/manual/en/function.openssl-seal.php)

When you Google for it there are also implementations for other languages available.

_b8r02• 15 years ago

PGP/GPG?

tptacek5• 15 years ago

It's not the RSA key size that prevents you from using RSA for arbitrary message lengths. Notice that block ciphers used for bulk encryption are similarly constrained by their block length (which are far shorter than an RSA key). In both RSA and AES, you can use a chaining construction to encrypt arbitrary-length messages.

The things that keep you from doing this in the real world with RSA are security and speed.

It's first of all much slower to perform a single RSA operation than it is to perform the AES block transform. AES involves no bignum math at all, let alone bignum modular multiplication.

Secondly and more importantly, RSA encryption is fundamentally volatile and dangerous. As an exercise, go implement it in Python or Ruby (you're going to find it's remarkably easy, since both those languages automatically promote to bignums). RSA is just a simple formula. As a result, there are a variety of pitfalls to using it safely. Among the important ones is the fact that you can't safely encrypt related messages, and that messages require a certain proportion of random padding.

asharp4• 15 years ago

Why don't you use the standard openssl RSA encryption function to encrypt the entire file, rather then encrypt a plaintext passphrase?

I don't know of an implementation that uses RSA encryption that doesn't use RSA to encrypt a (heavily padded, very random) key which they then use to encrypt the final payload using say AES or IDEA (in the original PGP).

asymptotic4• 15 years ago

Speed, because cryptanalysis via cipher-text only attacks becomes easier as you get more and more ciphertext associated with a given key, and because if someone attempts to analyse a memory core dump or the memory space of your computer hopefully the only data available is the session key, rather than the full decrypted RSA private key.

See:

https://secure.wikimedia.org/wikipedia/en/wiki/Session_key

https://secure.wikimedia.org/wikipedia/en/wiki/Ciphertext-on...

http://academic.csuohio.edu/zhao_w/teaching/Old/EEC693-S07/l...

asharp4• 15 years ago

That makes no sense.

You create some random key K.

You encrypt k using the public key of the recipient, ie. e(k).

You encrypt the message using K.

You send both of those to the recipient. A cyphertext only attack can recover K from your message M. It is not then possible to recover a private key from K.

In neither case do you ever have the private key, as such it cannot ever be recovered from a core dump. In this script it seems like they are simply doing this twice, for some unknown reason.

_b8r02• 15 years ago

So it appears that this site has the perceived advantage of turning a web developer's SSL cert into key for encryption, which at first sounds like a good idea.

If on the other hand you don't exclusively communicate with SSL-using web developers, you're better off using a PGP implementation. Unfortunately Symantec bought PGP Corporation, but GPG4Win[1] is free, as are GPG-based PGP implementations for almost every other platform.

Worried about it being hard? It really isn't. In fact it's easy to get up and running with encrypting your Gmail in Firefox[2] even if you have a Mac or something else[3].

[1] http://www.gpg4win.org/

[2] http://www.instructables.com/id/Send-and-Receive-Encrypted-E...

[3] http://www.instructables.com/id/Encrypt-your-Gmail-Email/

defen• 15 years ago

If you use the Firefox Gmail extension, watch out for the autosave drafts feature of Gmail, which will put a bunch of copies of your unfinished unencrypted email on Google's servers.

jevinskie• 15 years ago

Can you point me to a site that discusses the best practices for generating and securing my keypair? I don't have enough faith in an Instructable to get all the details right. How would I go about becoming part of this "web of trust" that I keep hearing about in relation to PGP.

tptacek5• 15 years ago

While there are Internet services that purport to realize an actual "web of trust", the "web of trust" concept is really notional. It's more an idea than a thing. The idea is, instead of having a central authority that vouches for every key, you get your keys directly from your acquaintances, verify them directly with your acquaintances, and in turn vouch for those keys with your peers.

kgo• 15 years ago

The GNU Privacy Handbook does a pretty good job of blending both the how and why of everything.

http://www.gnupg.org/gph/en/manual.html

The biggest thing to worry about is that you only want the private key on systems you trust. If you put your private key on a USB stick, and use the local library or computer lab, you've already lost the battle. If you're running a totally infected Win95 machine, you've already lost the battle.

Second biggest thing is to make sure you properly generate a revocation certificate, and a backup, and store them in a location you consider secure. (And maybe that secure location is just a shoebox in your bedroom closet unless you're worried about the NSA or something.) Then if you realize you've done something stupid, you can just revoke the key and create a new one.

Other than that, there's not much to screw up if you follow the default settings when creating a key with gpg.

For email, I would also highly recommend using a local MUA that connects to gmail. Most people use Thunderbird + Enigmail, but there are other options. Enigmail also has a pretty good manual that covers both the how and why.

http://enigmail.mozdev.org/documentation/handbook.php.html

The various gpg-related mailing lists are also pretty friendly. They're low-traffic enough that people are always happy to answer basic questions; no RTFM replies.

adamtj• 15 years ago

Here's what he's using it for: http://vulnarb.com/

It's not for communicating with web developers. It's for publicly and provably, but responsibly exposing vulnerabilities in software. The people/entities who write such software are likely to have a public website with SSL. If they don't, it's unlikely to be very important or widely used software. In that context, PGP makes no sense.

jojo12• 15 years ago

Using /dev/urandom as password source is a very bad idea.

asymptotic4• 15 years ago

Agreed. /dev/urandom should be mixed with other sources of entropy (system statistics, epoch, low-level counters, cryptographic PRNGs like Yarrow) and then "combined" using a cryptographic hash. Such a principle is used in e.g. Fortuna.

See:

https://secure.wikimedia.org/wikipedia/en/wiki/Fortuna_%28PR...

jojo12• 15 years ago

Or just use /dev/random :)

y0ghur7_xxx• 15 years ago

Care to explain why?

thamer• 15 years ago

A counterpart to /dev/random is /dev/urandom ("unlocked"/non-blocking random source) which reuses the internal pool to produce more pseudo-random bits. This means that the call will not block, but the output may contain less entropy than the corresponding read from /dev/random. While it is still intended as a pseudorandom number generator suitable for most cryptographic purposes, it is not recommended for the generation of long-term cryptographic keys.

http://en.wikipedia.org/wiki//dev/random

asharp4• 15 years ago

On virtual machines, /dev/urandom contains very little if any entropy.

Basically /dev/random takes entropy from the system and feeds it to you.

/dev/urandom is a psudorandom number generator that reseeds from entropy as it gets it. Ie. if it has no entropy, your random numbers are anything but random.

tptacek5• 15 years ago

Using /dev/urandom as a password source is fine. It's a CSPRNG. It theoretically degrades if you exhaust entropy, but there's no current attack I know of based on that property. Also, RNG attacks are usually "online", meaning an attacker gets to continually interact with the RNG. This is a one-off offline use. In this scenario, you could probably survive with rand().

asymptotic4• 15 years ago

It goes without saying that you shouldn't do a simple "rm" on the password file. I'm not going to put on my tin-foil hat and start gibbering about magnetic alignment and electron tunnel microscopy but this is just "one of those things" that everyone knows to avoid.

jvdongen• 15 years ago

While it is a nice idea, I do not see any practical applications.

It requires a receiver who is a) knowledgeable enough to decrypt it using something like openssl and b) have access to the actual private key.

If that's the case it is highly likely that this person is either capable of using something like PGP or facilitate a file upload form on the apparently available website. Both of which are at least as secure and a whole lot more convenient.

Something related to this I would be really interested in would be a way to encrypt a file client-side, in the browser using javascript prior to uploading it (without the need for the user to do special tricks beyond picking a password). So far this only seems remotely possible using something like flash or silverlight.

hendler• 15 years ago

I could see it being useful if you aren't sure how to get an encrypted message to some one.

Much encryption can be done in javascript.

https://ziyan.info/2008/10/javascript-rsa/

http://www-cs-students.stanford.edu/~tjw/jsbn/

http://www.beanizer.org/site/index.php/en/Articles/Practical...

bigmac• 15 years ago

Javascript is too hostile an environment for crypto. How do you know your js crypto code wasn't modified in transit? You use SSL. Now that you're using SSL why do you need encryption in the js at all?

Lennie• 15 years ago

Whoever thinks someone didn't change the code on the server might also be kidding himself...

pnathan2• 15 years ago

I suggest you patch the call to rm with a call to srm:

http://en.wikipedia.org/wiki/Srm_(Unix)

apgwoz• 15 years ago

...or at least use shred(1) and then rm(1)

pnathan2• 15 years ago

Six of one, half a dozen of the other?

Also note that there are interesting complications in relation to file data long-term storage on SSD drives. It should be investigated.

AdmiralBeotch• 15 years ago

Better to mount /dev/ram0 and do your encryption there. Then shred; rm -rf; umount for the win.

jrockway• 15 years ago

Instead of 'echo "QUIT" | openssl ...', why not 'openssl ... < /dev/null'?

Encrypt a file so that only a SSL site's private key can decrypt

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