Author Topic: The big elephant in the room with PGP  (Read 953 times)

ColorBlack

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The big elephant in the room with PGP
« on: October 13, 2013, 11:03:03 pm »
Don't mean to start the old PGP debate again.. and for the record, I USE PGP and trust it fully.
THAT being said, I was having a conversation with my man RxKing (who is on the record for his unwavering stance that PGP won't hurt, but it will not help if push comes to shove).

Guys.. I think there's an elephant in the room that isn't being addressed. If you recall in the criminal charge sheet against DPR... there are conversations quoted in there that were (at the time thought to be) PGP encrypted. Discussions DPR had with certain characters and Stexo (confirmed by himself) that were encrypted via PGP. Yet there everything was, in full glory.

Therefore there is obviously an elephant in the room it seems lots of us are avoiding. PGP is great, no doubt about it. But if LE gets your PGP password? Then it's utterly fucking useless... DPR case is the prime example. I don't think they "cracked" his PGP no. I doubt the he was that important that the NSA dedicated serious resources to cracking it (assuming they can even do that). No, they had his PGP password. How? I don't know and don't even want to even know.. this case is so fucked up and confusing and shocking that I wouldn't put it past the feds to have installed a camera in the guy's room and zoomed in as he typed.. or keylogged his laptop.. or possibly poor old DPR made the mistake of making his password "altoidfrosty" and they guessed it! Who knows! But the point is.. PGP is impenetrable.. until you get to the password. And if someone has the password, it's just another password lock. Like Gmail or whatever. Once they have your password, they're in.

I know there's technical issues I'm leaving out and thats left for people far smarter then me..

But consider this. Had DPR used Privnote for all communication.. (AND NO IM NOT ENDORSING OR VOUCHING FOR PRIVNOTE).. those conversations he had would have been destroyed upon each read. So, when the feds imaged the server.. and went into DPR's inbox to read all his communications.. they saw nothing but dead Privnote links that have no meaning to them other then "this message was already read". Instead, they found a bunch of PGP encrypted discussions..and since they had his PGP key..they put together a damning affidavit.


derrible

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Re: The big elephant in the room with PGP
« Reply #1 on: October 13, 2013, 11:17:49 pm »


But consider this. Had DPR used Privnote for all communication.. (AND NO IM NOT ENDORSING OR VOUCHING FOR PRIVNOTE).. those conversations he had would have been destroyed upon each read. So, when the feds imaged the server.. and went into DPR's inbox to read all his communications.. they saw nothing but dead Privnote links that have no meaning to them other then "this message was already read". Instead, they found a bunch of PGP encrypted discussions..and since they had his PGP key..they put together a damning affidavit.

Valid concerns about PGP, but if the only "flaw" in the system is that a password can potentially be obtained, isn't that inevitably a flaw with any system?

 Regarding privnote, I've always wondered if anyone could potentially validate whether the site really does delete all its messages upon being stored. 

Great God Pan

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Re: The big elephant in the room with PGP
« Reply #2 on: October 13, 2013, 11:23:21 pm »
I assume the conversations you're talking about are the ones he was having with the undercover fed hit-men?  It doesn't matter what you use if you talk with a fed.  They're recording the conversation on their end so there is no privacy.

There's a paradigm to describe the case where you may wish to protect old conversations if on of the keys is compromised.  It's called Perfect Forward Secrecy.  PGP does not provide PFS.  Other tools do, and it's up to the user to decide when a conversation needs PFS.   
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orange

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Re: The big elephant in the room with PGP
« Reply #3 on: October 13, 2013, 11:24:07 pm »
Don't mean to start the old PGP debate again.. and for the record, I USE PGP and trust it fully.
THAT being said, I was having a conversation with my man RxKing (who is on the record for his unwavering stance that PGP won't hurt, but it will not help if push comes to shove).

Guys.. I think there's an elephant in the room that isn't being addressed. If you recall in the criminal charge sheet against DPR... there are conversations quoted in there that were (at the time thought to be) PGP encrypted. Discussions DPR had with certain characters and Stexo (confirmed by himself) that were encrypted via PGP. Yet there everything was, in full glory.

Therefore there is obviously an elephant in the room it seems lots of us are avoiding. PGP is great, no doubt about it. But if LE gets your PGP password? Then it's utterly fucking useless... DPR case is the prime example. I don't think they "cracked" his PGP no. I doubt the he was that important that the NSA dedicated serious resources to cracking it (assuming they can even do that). No, they had his PGP password. How? I don't know and don't even want to even know.. this case is so fucked up and confusing and shocking that I wouldn't put it past the feds to have installed a camera in the guy's room and zoomed in as he typed.. or keylogged his laptop.. or possibly poor old DPR made the mistake of making his password "altoidfrosty" and they guessed it! Who knows! But the point is.. PGP is impenetrable.. until you get to the password. And if someone has the password, it's just another password lock. Like Gmail or whatever. Once they have your password, they're in.

I know there's technical issues I'm leaving out and thats left for people far smarter then me..

But consider this. Had DPR used Privnote for all communication.. (AND NO IM NOT ENDORSING OR VOUCHING FOR PRIVNOTE).. those conversations he had would have been destroyed upon each read. So, when the feds imaged the server.. and went into DPR's inbox to read all his communications.. they saw nothing but dead Privnote links that have no meaning to them other then "this message was already read". Instead, they found a bunch of PGP encrypted discussions..and since they had his PGP key..they put together a damning affidavit.

And that is why messages are to be deleted upon reception. And that also explains me having a BIG problem with the staff stance on "encrypted backups of messages".
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WestleyR

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Re: The big elephant in the room with PGP
« Reply #4 on: October 13, 2013, 11:47:00 pm »
As far as I understood PGP they need the "private key" AND "password"???
So in my view they ether were part of the conversation or it wasn't encrypted at all.
Correct me if I'm wrong.
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Sarge

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Re: The big elephant in the room with PGP
« Reply #5 on: October 14, 2013, 12:11:58 am »
This is just spreading false information.

The previous post was correct, The cops would need the private PGP key + the password in question. I never read any information that lead me to believe anyone's PGP was cracked.

PGP is our best line of defense.  & everyone should use 3072 bit or larger key.

IS PGP future proof? No.. However it definitely makes the cops jobs a lot harder.. 
« Last Edit: October 14, 2013, 12:22:27 am by Sarge »
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Great God Pan

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Re: The big elephant in the room with PGP
« Reply #6 on: October 14, 2013, 12:30:31 am »
BTW, try to teach cops about PGP and how to use it, GOOD FUCKING LUCK!
They can barely talk on ICQ to girls when they are bored at the station.

No cops allowed in PGP Club.
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WestleyR

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Re: The big elephant in the room with PGP
« Reply #7 on: October 14, 2013, 12:38:04 am »
BTW, try to teach cops about PGP and how to use it, GOOD FUCKING LUCK!
They can barely talk on ICQ to girls when they are bored at the station.

No cops allowed in PGP Club.

:D
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Just Chipper

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Re: The big elephant in the room with PGP
« Reply #8 on: October 14, 2013, 12:54:15 am »
If you recall in the criminal charge sheet against DPR... there are conversations quoted in there that were (at the time thought to be) PGP encrypted.

But if LE gets your PGP password? Then it's utterly fucking useless.

No, they had his PGP password. How?

But the point is.. PGP is impenetrable.. until you get to the password.

Had DPR used Privnote for all communication.. those conversations he had would have been destroyed upon each read. So, when the feds imaged the server.. and went into DPR's inbox to read all his communications.. they saw nothing but dead Privnote links that have no meaning to them other then "this message was already read".

Yes. Although as Ulbricht used his real name for an email address I have my doubts that he used a passphrase with an acceptable amount of entropy.

As is essentially everything that uses a password.

My guess is they waited for him to input the passphrase himself then swarmed him before he could power off his laptop.

That's like saying "This safe is impenetrable... unless you have the key". Of course if they get your key you're screwed.

For not promoting Privnote you sure are adamant about using it. Biases aside that's a terrible idea. It introduces unnecessary counter-party risk (Privnote Admins). You aren't in control of the private key despite what Privnote Admins tell you. They generate the private key on THEIR server then ONLY give it to you (Don't worry they promised), and finally delete the message from the database (Pinky promise). There are numerous other vulnerabilities but I'm not going to waste time typing them.

Regarding privnote, I've always wondered if anyone could potentially validate whether the site really does delete all its messages upon being stored.

IMO it's impossible.

As far as I understood PGP they need the "private key" AND "password"?

Yes. But his private key was on the laptop he was using when they arrested him. As numerous sources have stated they waited until he "logged in" to his laptop. But I believe they waited longer than that for him to input his PGP passphrase as well.
« Last Edit: October 14, 2013, 06:03:03 am by Just Chipper »
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WestleyR

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Re: The big elephant in the room with PGP
« Reply #9 on: October 14, 2013, 01:01:38 am »
Stay on the timeline. The PDF we all have read was written before they got him in the library. So they had this conversation before that point of time.


P.S.:why do u sign every message? :D
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frosty@frosty

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Re: The big elephant in the room with PGP
« Reply #10 on: October 14, 2013, 02:23:55 am »

Guys.. I think there's an elephant in the room that isn't being addressed. If you recall in the criminal charge sheet against DPR... there are conversations quoted in there that were (at the time thought to be) PGP encrypted. Discussions DPR had with certain characters and Stexo (confirmed by himself) that were encrypted via PGP. Yet there everything was, in full glory.


One of the possibilities is that some of the people DPR was communicating with are cooperating with the authorities. Like the "Employee" he tried to have killed. Once they compromise one party in the conversation PGP is useless.

It does seem like they were able to decrypt DPRs messages well before they arrested him. Its very possible that they put a hardware keylogger on his computer. The feds have used this tactic in the past to get passwords to encrypted files before an arrest.  Its strange that they don't seem to have gotten the password to his bitcoin wallet , if the press reports are to be believed. I guess that means he never entered the password the whole time they had him under surveillance.

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Re: The big elephant in the room with PGP
« Reply #11 on: October 14, 2013, 02:33:56 am »
As far as I understood PGP they need the "private key" AND "password"???
So in my view they ether were part of the conversation or it wasn't encrypted at all.
Correct me if I'm wrong.

You are correct -- both the PGP private key, as well as the passphrase are needed to decrypt encrypted messges.

Nightcrawler
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Re: The big elephant in the room with PGP
« Reply #12 on: October 14, 2013, 02:46:13 am »
BTW, try to teach cops about PGP and how to use it, GOOD FUCKING LUCK!
They can barely talk on ICQ to girls when they are bored at the station.

No cops allowed in PGP Club.

And how, precisely, do you propose keeping them out?

Nightcrawler
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AlternateReality

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Re: The big elephant in the room with PGP
« Reply #13 on: October 14, 2013, 02:51:00 am »
I wonder if the NSA really could crack a PGP key. I mean provided you have enough time + resources its technically possible, right?

frosty@frosty

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Re: The big elephant in the room with PGP
« Reply #14 on: October 14, 2013, 02:56:15 am »
Why do you say they seem to have decrypted his messages?

What would make you think this?

Please show us where in any of the papers.

Read the quote from the original post. Somebody named Stexo claims that communications he had with DPR which were encrypted with PGP are in the Criminal Complaint document. You have to believe that all the stuff about DPR discussing having "FriendlyChemist" killed must have been encrypted , soo how did the FBI have the cleartext before the arrest ?

Great God Pan

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Re: The big elephant in the room with PGP
« Reply #15 on: October 14, 2013, 03:07:50 am »
BTW, try to teach cops about PGP and how to use it, GOOD FUCKING LUCK!
They can barely talk on ICQ to girls when they are bored at the station.

No cops allowed in PGP Club.

And how, precisely, do you propose keeping them out?

Nightcrawler
4096R/BBF7433B 2012-09-22 Nightcrawler <Nightcrawler@SR>
PGP Key Fingerprint = D870 C6AC CC6E 46B0 E0C7  3955 B8F1 D88E BBF7 433B

Please excuse the jest; it was not a serious comment.


I wonder if the NSA really could crack a PGP key. I mean provided you have enough time + resources its technically possible, right?

The current record for RSA factorization is RSA-768, which was done on December 12, 2009.  It took two years and hundreds of computers.  The problem of factoring a 1024 RSA modulus is estimated to be 1000 times harder.  Extrapolate that out to 2048 or 4096 bit RSA.  Nevertheless, the Great God Pan recommends using the largest size RSA key allowed by your PGP software.  Currently that seems to be 4096 bit RSA in most cases.
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OperationsSecurity(OPSEC)

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Re: The big elephant in the room with PGP
« Reply #16 on: October 14, 2013, 07:35:09 am »
The big elephant in the room with PGP is no Perfect Forward Secrecy (PFS) meaning if I brute force, key log, or watch you type in your password then I can decrypt everything you've ever encrypted. PFS means a new key is generated for each sessions and then discarded, so if feds kick down your door and you're using OTR they can only get the current chat session, they can't go back in time and decrypt everything because those private keys are gone.

PGP needs to die, it's shit 90s technology. Pond is a good replacement, so is TextSecure once it becomes fully data and can be used for desktops.

Edit: Zimmerman, who invented PGP, doesn't even use it anymore.
« Last Edit: October 14, 2013, 08:06:43 am by OperationsSecurity(OPSEC) »
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0xfffe

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Re: The big elephant in the room with PGP
« Reply #17 on: October 14, 2013, 08:08:31 am »
No cops allowed in PGP Club.

And how, precisely, do you propose keeping them out?


They might all be his buddies from the cybercrime department ;D

Just Chipper

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Re: The big elephant in the room with PGP
« Reply #18 on: October 14, 2013, 02:19:02 pm »
Uh no thanks, Zimmerman is not involved with felony level crime every day...
All the crinimals I know of use fucking PGP.

I don't see how that's relevant?

I'm betting that a lot of them also use IRC with OTR, right? That is the same protocol in TextSecure that OPSEC is suggesting.
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fuckingnoobsnfuckingfeds

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Re: The big elephant in the room with PGP
« Reply #19 on: October 15, 2013, 12:25:52 am »
Look you fucking idiots and feds. GPG is very safe. Not much (available software) is safer than GPG for secure encrypted communications. If people use privnote, they are weak to MITM. Privnote is WORTHLESS. The goal of a communications encryption system is to protect communications between Alice and Bob from a malicious Eve who can view the channel between them. GPG does this by a mixture of an asymmetric algorithm such as RSA and a symmetric algorithm such as AES. When Alice writes a message to Bob, first a pseudorandom number generator generates a long session key, then the session key is fed to the symmetric algorithm to encrypt the Alice's plaintext. Then the session key is encrypted with Bob's public key. The final message is sent to Bob, it is a combination of the asymmetrically encrypted session key and the ciphertext. When Bob gets the message he needs to type his password in because his private key is stored symmetrically encrypted. Bob's password is used with a password based key derivation function (PBKDF) to generate a key that is used to decrypt the symmetrically stored asymmetric key, and then the asymmetric key in its plaintext form is used to decrypt the session key of the message from Alice. Then, the session key is used to decrypt the ciphertext and Bob gets the plaintext message from Alice. Since Eve doesn't have Bob's private key, she cannot decrypt the message even if she can see Alice send the message to Bob and obtain the ciphertext. Now, of course if Eve has Bob's private key she can decrypt the message. The only way to get the private key from Bob is to get a copy of it and decrypt it with Bob's password. GPG cannot really protect you from this, it already protects you as much as it can by storing your private key encrypted symmetrically in the first place. But if Eve uses a keylogger or a hidden camera, she can probably get enough passphrases and passwords from Bob to be able to get to private key and decrypt it. This is why Bob uses Tor to protect from traffic analysis, so Eve can not find him to target him in such a way. This is also why Bob uses traditional computer security, such as isolation, to make it so Eve can not get his passwords/keys via remotely hacking him. The biggest threat left for the GPG threat model in this case is that Eve could do a man in the middle attack, tricking Bob into thinking he has Alice's key and Alice into thinking she has Bob's key, when in reality they both have Eve's key, and Eve can then intercept messages and decrypt them prior to encrypting them again with the real key of Alice or Bob. This is a threat if Eve controls the channel Alice and Bob communicate over for the entire time, if Alice and Bob have done a legitimate key exchange before Eve takes over the channel they are still protected. It is always a good idea to have a few independently operated channels that you are in touch with a contact over, because then you can do key exchange or fingerprint verification through multiple channels and be protected from Eve doing a MITM attack unless she controls all of the channels. You can also use shared secrets and various other techniques to try to protect from this sort of MITM attack, there are various advanced techniques that can minimize the risk and maximize the probability of detection as well.

Now let's look at what privnote is. Privnote is a website that sends you a javascript script. This script could be malicious, even if you independently verify it is legitimate at one time, unless you verify it every single time it could be selectively bugged. Every time you get the script you either need to verify it is legitimate or risk it being bugged part of the time. Also, javascript is not a language that is any good for implementing cryptography for a variety of reasons, so not only is there a risk that the script can be bugged but there is also a certainty that the script is not ideal for cryptography anyway. But even if we assume that the script is ideal for cryptography, the system still fucking sucks. The shitty possibly bugged javascript script is sent to you, and then it generates a session key. The session key is then used to encrypt your plaintext message, and then the ciphertext is sent to the privnote server. At this point, assuming the script wasn't bugged (it could have been) or full of exploitable side channels (it probably is), privnote only has your ciphertext and an index it is stored under, so they cannot get the plaintext. Except now, you send this index AND the PLAINTEXT session key to Bob, over the channel. Guess what! Now if Eve owns the channel, she can MITM this session key. It isn't even encrypted, so every single time you send a message it is vulnerable. With GPG you are safe if Eve owns the channel AFTER a key exchange, with privnote you are FUCKED AFTER EVE OWNS THE CHANNEL, EVEN IF SHE DID NOT OWN IT WHEN YOU FIRST STARTED TALKING TO BOB. With Privnote, every single message is a key exchange, and not even an asymmetric key exchange, but a symmetric key exchange, and not just a symmetric key exchange, but a symmetric key exchange that also points to the ciphertext the symmetric key decrypts. Privnote is essentially you uploading a truecrypt container with your message in it to a server, and then sending the password to the container and a link to it to Bob. See how fucking stupid that is? With GPG you are fucked if the attacker finds you to get your private key, or hacks you and steals it, and gets your password. With Privnote, YOU SEND YOUR PASSWORD TO DECRYPT AN INDIVIDUAL MESSAGE WITH EVERY SINGLE INDIVIDUAL MESSAGE. Privnote destroys messages after they are read, but that doesn't mean that Bob wont make a copy and it doesn't mean that Eve wont read the message and let it be deleted and then make another copy of the same damn message and send Bob the key and link to that message. Privnote is worthless of every single level. It will amaze me to learn that it is not a federal wiretapping project trying to trick people into thinking they can use it safely, while in reality in trivially enables the feds to wiretap the people who use it to send messages over channels that they control.

If DPR or anyone else used privnote, every single fucking message they sent for the past three months would have 100% certainly have been compromised, since the feds owned the server for that long. For 3 months the feds were the Eve who owned the channel between Alice and Bob, people who had already done GPG key exchange prior to this were totally safe from them. People who used privnote were at high risk of having all of their messages sent over this period of time intercepted and viewed in plaintext by the feds, it would be even easier to do MITM against these people than people exchanging GPG keys over this time period, because the feds could get court orders against privnote making them cooperate in MITM attacks so they didn't even need to delete previous messages, the feds could just order privnote to not delete messages viewed by some federal IP address, and had at it viewing messages with the URL's and keys to decrypt them that they intercepted passing through the server, without the message being deleted, and then the vendor thinks he looks at it for the first time and views the same message and then it is deleted. This wouldn't even really be possible to detect if they did a MITM attack in this way, whereas if they did MITM attacks against GPG key exchanges it could have been detected if people were using advanced MITM detection techniques.

So in short, fuck off with this Privnote nonsense, it is bullshit from the ground up, it is broken from the ground up, everything about it sucks and it is not worth another second of thought. Anyone suggesting privnote is at high risk of being a fed, straight up.
« Last Edit: October 15, 2013, 12:42:26 am by fuckingnoobsnfuckingfeds »

fuckingnoobsnfuckingfeds

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Re: The big elephant in the room with PGP
« Reply #20 on: October 15, 2013, 12:32:08 am »


But consider this. Had DPR used Privnote for all communication.. (AND NO IM NOT ENDORSING OR VOUCHING FOR PRIVNOTE).. those conversations he had would have been destroyed upon each read. So, when the feds imaged the server.. and went into DPR's inbox to read all his communications.. they saw nothing but dead Privnote links that have no meaning to them other then "this message was already read". Instead, they found a bunch of PGP encrypted discussions..and since they had his PGP key..they put together a damning affidavit.

Valid concerns about PGP, but if the only "flaw" in the system is that a password can potentially be obtained, isn't that inevitably a flaw with any system?

 Regarding privnote, I've always wondered if anyone could potentially validate whether the site really does delete all its messages upon being stored.

He could have used a system with perfect forward secrecy, like OTR. Everytime someone wanted to communicate with DPR, he could have generated what is called an 'ephemeral' keypair. Usually this is done with DH and ECDH. His contact (Alice) would generate an ephemeral ECDH key and sign it with her long term ECDSA key, then send it with a message to DPR saying she wanted to talk to him. DPR would verify the signature on the key, and then generate an ephemeral ECDH keypair, he would use Alice's public key and his private key to derive a shared secret. Then he would send the ephemeral public key to Alice, who would use it with her ephemeral private key to generate an equal shared secret. This shared secret could then be used to symmetrically encrypt a message that Alice sends to DPR, and DPR then decrypts it with the shared secret. At this point the secrets can all be deleted. Any future messages would need to take the same protocol. This is actually a really rough protocol and normally it would not happen exactly like this, but I am tired and just trying to show how a cryptosystem with perfect forward secrecy works, in reality it could be simplified a bit. OTR works in a way fairly similar to this actually.

fuckingnoobsnfuckingfeds

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Re: The big elephant in the room with PGP
« Reply #21 on: October 15, 2013, 12:35:15 am »
Quote
For not promoting Privnote you sure are adamant about using it. Biases aside that's a terrible idea. It introduces unnecessary counter-party risk (Privnote Admins). You aren't in control of the private key despite what Privnote Admins tell you. They generate the private key on THEIR server then ONLY give it to you (Don't worry they promised), and finally delete the message from the database (Pinky promise). There are numerous other vulnerabilities but I'm not going to waste time typing them.
Quote

Actually you generate the key client side with the javascript script that they send you, but it doesn't matter because the system is still shit in multiple different ways.

fuckingnoobsnfuckingfeds

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Re: The big elephant in the room with PGP
« Reply #22 on: October 15, 2013, 12:40:58 am »
Uh no thanks, Zimmerman is not involved with felony level crime every day...
All the crinimals I know of use fucking PGP.

The big elephant in the room with PGP is no Perfect Forward Secrecy (PFS) meaning if I brute force, key log, or watch you type in your password then I can decrypt everything you've ever encrypted. PFS means a new key is generated for each sessions and then discarded, so if feds kick down your door and you're using OTR they can only get the current chat session, they can't go back in time and decrypt everything because those private keys are gone.

PGP needs to die, it's shit 90s technology. Pond is a good replacement, so is TextSecure once it becomes fully data and can be used for desktops.

Edit: Zimmerman, who invented PGP, doesn't even use it anymore.

He actually is kind of right. GPG and PGP are really good, and you shouldn't be worried about using them for sensitive things. But they are using old algorithms. And they are not as advanced as they could be. Encrypted messaging systems could be significantly more user friendly and secure than GPG. OTR comes to mind as one such system. The problem with OTR is that it is quite weak to MITM attacks unless you know how to properly use it, and most people don't know how to. If you don't have a symmetrically encrypted database of 256 bit shared secrets, you probably are not using OTR to its full security potential.

Right now, all of the cutting edge implemented security systems are outdated compared to the state of the art in theory. There is actually an enormous gap between theory and practice, for anonymizers, for encryption, etc. We know of theoretical systems that are much better than most all of the systems actually being used in practice today. But none of them exist outside of the realm of academic whitepapers.
« Last Edit: October 15, 2013, 12:44:37 am by fuckingnoobsnfuckingfeds »

ChemCat

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Re: The big elephant in the room with PGP
« Reply #23 on: October 15, 2013, 12:46:09 am »
Quote from: fuckingnoobsnfuckingfeds

He actually is kind of right. GPG and PGP are really good, and you shouldn't be worried about using them for sensitive things. But they are using old algorithms. And they are not as advanced as they could be. Encrypted messaging systems could be significantly more user friendly and secure than GPG. OTR comes to mind as one such system. The problem with OTR is that it is quite weak to MITM attacks unless you know how to properly use it, and most people don't know how to. If you don't have a symmetrically encrypted database of 256 bit shared secrets, you probably are not using OTR to its full security potential.

Right now, all of the cutting edge implemented security systems are outdated compared to the state of the art in theory. There is actually an enormous gap between theory and practice, for anonymizers, for encryption, etc. We know of theoretical systems that are much better than most all of the systems actually being used in practice today. But none of them exist outside of the realm of academic whitepapers.


     ^^^^



+1  :)
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whom

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Re: The big elephant in the room with PGP
« Reply #24 on: October 15, 2013, 02:06:32 am »
He actually is kind of right. GPG and PGP are really good, and you shouldn't be worried about using them for sensitive things. But they are using old algorithms. And they are not as advanced as they could be. Encrypted messaging systems could be significantly more user friendly and secure than GPG. OTR comes to mind as one such system. The problem with OTR is that it is quite weak to MITM attacks unless you know how to properly use it, and most people don't know how to. If you don't have a symmetrically encrypted database of 256 bit shared secrets, you probably are not using OTR to its full security potential.

PGP/GnuGPG is awful.  The crypto is starting to age poorly (especially the PBKDF methods ), the user interface sucks, it's a huge pain in the ass.   And it'll probably still be around twenty years from now, with increasingly improved crypto, and just as shitty of a user interface.

It, or something like it (and you could certainly improve significantly on it) will always be useful whenever you need to asymmetrically encrypt something to someone (who isn't online right now and standing around waiting for your message) and the goal is to create an encrypted object that can sit there forever and remain readable by the recipient. i.e. On a mail server for six hours until somebody checks their mail, or on your hard drive until the day you die. 

The core problem is that we're going to have to move away from needing to store encrypted communications in their original form after we receive them.  PGP makes it too easy.  You send me a message, I decrypt and read it, then throw the ciphertext in an archive "in case I wanna read it again".   Five years later, your message is still on my hard drive, still provably from you.  To me.  With whatever contents it has.

I'm embarrassed to say that I've spent much of my life saying shit like "A benefit of PGP is that it provides non-repudiation.".  Benefit?  That twenty years from now, you can mathematically prove that I said something?  Fuck that.  As soon as you get my message, as long as *you* are convinced it's from me and has integrity, I want that bad-boy to be completely without any verifiable integrity whatsoever.  Once you trust it, the need for trust goes out the window.    OTR gets that part perfectly right.

fuckingnoobsnfuckingfeds (love typing that name, BTW) and OPSEC are right that OTR and similar technologies are the way to go.   But before those technologies, or anything like them, will *replace* PGP, we'll also have to agree to replace how we're using it.

PFS/OTR/etc can secure the actual act of *communication* between two parties, but not the messages before or after they've been communicated.

So if the only secure way to communicate is in real-time (i.e. chat/IM/voice, not store-and-forward email), that seems weird at first. but maybe not..  A hundred years ago, I'm pretty sure people walked away from the crowd and whispered face to face when they had secret shit to say, and wrote long lettters to each other when they weren't worried about who read them.

Quote
Right now, all of the cutting edge implemented security systems are outdated compared to the state of the art in theory. There is actually an enormous gap between theory and practice, for anonymizers, for encryption, etc. We know of theoretical systems that are much better than most all of the systems actually being used in practice today. But none of them exist outside of the realm of academic whitepapers.
Weird.  It's almost like all the smart guys were too busy telling stories to their grandkids about how "Grandpappy stuck it to The Man and stopped the Clipper Chip all by hisself!"

I think everybody in security has revised their view of the world in the past six months. 


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Re: The big elephant in the room with PGP
« Reply #25 on: October 15, 2013, 03:16:23 am »
fuckingnoobsnfuckingfeds (love typing that name, BTW) and OPSEC are right that OTR and similar technologies are the way to go.   But before those technologies, or anything like them, will *replace* PGP, we'll also have to agree to replace how we're using it.

PFS/OTR/etc can secure the actual act of *communication* between two parties, but not the messages before or after they've been communicated.

So if the only secure way to communicate is in real-time (i.e. chat/IM/voice, not store-and-forward email), that seems weird at first. but maybe not..  A hundred years ago, I'm pretty sure people walked away from the crowd and whispered face to face when they had secret shit to say, and wrote long lettters to each other when they weren't worried about who read them.

I think PGP is a very practical way to agree on and set up a PFS communication method if two people have something lengthy and sensitive to talk about.  As far as the market place goes, a simple one way communication compromising of a delivery address to a vendor is done very well with PGP.

« Last Edit: October 15, 2013, 03:17:04 am by Great God Pan »
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Re: The big elephant in the room with PGP
« Reply #26 on: October 15, 2013, 04:39:50 am »
This is just spreading false information.

The previous post was correct, The cops would need the private PGP key + the password in question. I never read any information that lead me to believe anyone's PGP was cracked.

PGP is our best line of defense.  & everyone should use 3072 bit or larger key.

IS PGP future proof? No.. However it definitely makes the cops jobs a lot harder..

Sarge - this has been addressed before by StExo multiple times. That he had conversations with DPR that were encrypted, that were quoted in the FBI warrant.
I didn't mean to imply anyone's PGP key was "cracked" per se.. I'm assuming more like hacked/keylogged or whatever. I definetly was astonished about this and remember reading a post StExo made clarifying that some of that affidavit was pulled from encrypted conversations between him and DPR.

Unles StExo (who we know to be very well versed in all things security/PGP) volunteered his communications with DPR to the feds because of some sick fetish to get himself in trouble (SARCASM!).. they definetly had DPR's key or passphrase..

tl;dr - the feds read encrypted messages meant for dpr

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Re: The big elephant in the room with PGP
« Reply #27 on: October 15, 2013, 05:35:56 am »
Sub
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Re: The big elephant in the room with PGP
« Reply #28 on: October 15, 2013, 05:38:25 am »
Unles StExo (who we know to be very well versed in all things security/PGP) volunteered his communications with DPR to the feds because of some sick fetish to get himself in trouble (SARCASM!).. they definetly had DPR's key or passphrase..

tl;dr - the feds read encrypted messages meant for dpr

There's one other scenario here that hasn't been addressed yet.

Its also possible that StExo encrypted his communications with DPR, and DPR either
1. Stored the unencrypted text somehwere the feds had access to
                ....or....
2. Replied to StExo, or forwarded the message to someone else in plain text, quoting the original message.

Sounds stupid, I know. But DPR also made other seemingly retarded miscalculations. Its not entirely out of the question
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oracle

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Re: The big elephant in the room with PGP
« Reply #29 on: October 15, 2013, 06:19:27 am »
Unles StExo (who we know to be very well versed in all things security/PGP) volunteered his communications with DPR to the feds because of some sick fetish to get himself in trouble (SARCASM!).. they definetly had DPR's key or passphrase..

tl;dr - the feds read encrypted messages meant for dpr

There's one other scenario here that hasn't been addressed yet.

Its also possible that StExo encrypted his communications with DPR, and DPR either
1. Stored the unencrypted text somehwere the feds had access to
                ....or....
2. Replied to StExo, or forwarded the message to someone else in plain text, quoting the original message.

Sounds stupid, I know. But DPR also made other seemingly retarded miscalculations. Its not entirely out of the question

DPR did keep logs of discussions in plain text. I'm not getting into it in major detail here, but to claim that DPR's PGP was compromised is an assumption. Rather unlikely. He absolutely kept conversations and correspondence that were initially fully encrypted both ways in plain text somewhere. Why? Only he can answer that question.

I had several conversations with him.. in which he was pasting parts of his conversations with others and/or discussing matters that I am prepared to bet my kidneys HAD to have been encrypted at some point due to their sensitive nature. And he replicated them in plain, clear text.. in real time, rapidly. Leading me to believe they were stored somewhere in plain-text simply for easy access.

This was not on the market site either. Meaning he was saving things and/or at-least partially leaving certain data unencrypted, somewhere.

To speculate this was cracked or that was hacked and this was key-logged is premature and pointless. Perhaps he was decrypting communications and leaving the clear text, hypothetically, in his Tormail (operating under the assumption that it was safe)? Perhaps he was not encrypting everything. I know for a fact that at times he was extremely cautious to encrypt.. and other times he was very laid back in his approach.

You must all realize that the Dread Pirate Roberts account has not signed into the forums since the night before his arrest. If the authorities had all his passwords and keys, they'd have logged in at some point as him and saved every single tidbit. The fact that "his account" hasn't logged in means there is much that the authorities do not have/he's not giving. The password to his encrypted BTC wallet(s) being another example.

This entire debate of PGP vs no PGP is rather pointless. PGP can and will save you to the extent that the keys/passphrases are not compromised, and to the extent that you are not leaving docs and data decrypted lying around thinking "that day" will never come.

It came.
« Last Edit: October 15, 2013, 06:21:13 am by oracle »
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Re: The big elephant in the room with PGP
« Reply #30 on: October 15, 2013, 06:26:12 am »
DPR communicated with informants and undercover cops as well, so any encryption wouldn't have mattered.
What does is the potentially hundreds of PMs and other history lying around the internet and his old server, that if the feds could get the private key for they would be able to read everything he has done for 2 years. New DPR needs a better system that doesn't keep around evidence
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and

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Re: The big elephant in the room with PGP
« Reply #31 on: October 15, 2013, 06:55:53 am »
They have a lot of funds and resources available.  There is no reason not to use some good technology while they have the chance.
They knew who he was for a long time and must have had many opportunities to prepare for the takedown.
There is so many ways they could have logged his password. They knew the cafe or library he used to visit, a well placed camera there and they could see what he wrote as password. They could have used a hardware or software keylogger. And the possibilitys does not stop there with todays technology it's possible to keylog with sound from the keyboard. (Source DEFCON, search and you shall find)

And they caught him right after he logged into his computer, so they had at least some parts of his system decrypted on the takedown.
If he did not have any more layer of protection they probably had the private key right away, there is also a possibility he had passwords written down on his computer.
It sounds stupid but it has happened before.
I'm sure many of you have done it too.
He was not as secure as he could have been, he is only human after all.
He could also have saved conversations unencrypted for easy access. Humans are very lazy and being secure require a lot of effort.

As they got at least 1 of his bitcoin wallets with a lot of money they must have had pretty deep access.
If there was one thing I would have kept very very safe it would have been my big BC wallet.

And as they have the servers and also possibly the forum they could just extract data directly from the database, that's how they work.
They save everything and work on it afterwards if possible. Just because it looks like he have not logged into the forums does not mean they can't have access to his account.
This is no smalltime case, they have resources to do everything properly, their way. If they was not ready to get what they wanted they would have waited with the bust until they were.
« Last Edit: October 15, 2013, 06:57:51 am by and »

fuckingfedsandnoobsohmy

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Re: The big elephant in the room with PGP
« Reply #32 on: October 16, 2013, 12:18:27 am »
Two big areas that GPG could improve in: perfect forward secrecy and quantum resistant asymmetric algorithms. We already know how to do both of these things, but nobody has made a message encryption system that uses both. OTR has PFS but it isn't quantum resistant. Nothing prevents someone from making a system like GPG with PFS, but it would probably require a somewhat different interface for it to not feel awkward to use. PFS is well suited to real time chat applications, less so for delayed messages. This is because both parties need to generate ephemeral keys to encrypt messages, but each party needs to have the other parties ephemeral public key. This means that generally it is going to require several back and forth communications to take place prior to being able to encrypt any single message, whereas GPG the way it is usually used has a single key exchanged and then no more back and forth is required other than the sending of encrypted messages themselves. There are several other improvements that could be made as well. Honestly, I have made systems more secure than GPG just fucking around with C and OpenSSL.

whom

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Re: The big elephant in the room with PGP
« Reply #33 on: October 16, 2013, 04:07:04 am »
But how do you ephemerally key something you need to be able to open after the communication occurs?  If the key is ephemeral, it's toast by the time the conversation is over.   

That was my point with PFS/ephemeral keying.  It's great for things in motion, but it seems useless for things at rest.  Maybe I'm missing something.  How can a key be ephemeral and permanent?  Isn't a key that still exists after the conversation non-ephemeral by definition?

I really think PFS only has strong value for real-time communications.  We'll always need a way to asymmetrically encrypt data. 

However, if you could send asymmetrically encrypted (but unsigned) messages (i.e. PGP or something better) OVER a PFS channel, then you could verify integrity using PFS *instead* of by having the sender cryptographically sign the message.  That would be a huge improvement.  You know the message is from me, but I don't have to sign it for you to know that.  So once it's on your hard drive, it's just some shit encrypted to your public key.  You could have done that.  Wasn't from me.   Still requires both parties online to do right, though.

We could always try encapsulating PFS over SMTP.    :)

ds

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Re: The big elephant in the room with PGP
« Reply #34 on: October 17, 2013, 02:18:54 pm »
What about if you generate a new keypair periodically, sign your new with your old and then securely delete the old? Isn't that a decent simulation of PFS?

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Re: The big elephant in the room with PGP
« Reply #35 on: October 17, 2013, 06:13:43 pm »
What about if you generate a new keypair periodically, sign your new with your old and then securely delete the old? Isn't that a decent simulation of PFS?

Sure, if you build yourself a web of trust through signing new keys, and nuking the older one's (and using the more recent keys to sign future ones) then yeah, you have poor man's not-so-perfect forward secrecy, just don't re-use passwords either.

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Re: The big elephant in the room with PGP
« Reply #36 on: October 17, 2013, 08:07:41 pm »
those conversations he had would have been destroyed upon each read.

It is unlikely that the conversations were "destroyed", more likely that the memory locations were marked as available for overwrite.

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Re: The big elephant in the room with PGP
« Reply #37 on: October 19, 2013, 06:12:36 am »
I wonder if the NSA really could crack a PGP key. I mean provided you have enough time + resources its technically possible, right?

PGP keys have been broken, in the past. The most famous of these is the 384-bit Blacknet key, circa June, 1995. Blacknet was the invention of Cypherpunk T.C. May and done as a thought experiment of sorts. Interestingly enough, he got a few interesting offers from Third World countries.  This key was later factored, and the newsgroup posts decoded.

You can read about Blacknet here:  http://groups.csail.mit.edu/mac/classes/6.805/articles/crypto/cypherpunks/blacknet.txt (clearnet)

Quote
Introduction to BlackNet


Your name has come to our attention. We have reason to believe you may be
interested in the products and services our new organization, BlackNet, has
to offer.

BlackNet is in the business of buying, selling, trading, and otherwise
dealing with *information* in all its many forms.

We buy and sell information using public key cryptosystems with essentially
perfect security for our customers. Unless you tell us who you are (please
don't!) or inadvertently reveal information which provides clues, we have
no way of identifying you, nor you us.

Our location in physical space is unimportant. Our location in cyberspace
is all that matters. Our primary address is the PGP key location:
"BlackNet<nowhere@cyberspace.nil>" and we can be contacted (preferably
through a chain of anonymous remailers) by encrypting a message to our
public key (contained below) and depositing this message in one of the
several locations in cyberspace we monitor. Currently, we monitor the
following locations: alt.extropians, alt.fan.david-sternlight, and the
"Cypherpunks" mailing list.

BlackNet is nominally nondideological, but considers nation-states, export
laws, patent laws, national security considerations and the like to be
relics of the pre-cyberspace era. Export and patent laws are often used to
explicity project national power and imperialist, colonialist state
fascism. BlackNet believes it is solely the responsibility of a secret
holder to keep that secret--not the responsibilty of the State, or of us,
or of anyone else who may come into possession of that secret. If a
secret's worth having, it's worth protecting.

BlackNet is currently building its information inventory. We are interested
in information in the following areas, though any other juicy stuff is
always welcome. "If you think it's valuable, offer it to us first."

- trade secrets, processes, production methods (esp. in semiconductors)
- nanotechnology and related techniques (esp. the Merkle sleeve bearing)
- chemical manufacturing and rational drug design (esp. fullerines and
protein folding)
- new product plans, from children's toys to cruise missiles (anything on
"3DO"?)
- business intelligence, mergers, buyouts, rumors

BlackNet can make anonymous deposits to the bank account of your choice,
where local banking laws permit, can mail cash directly (you assume the
risk of theft or seizure), or can credit you in "CryptoCredits," the
internal currency of BlackNet (which you then might use to buy _other_
information and have it encrypted to your special public key and posted in
public place).

If you are interested, do NOT attempt to contact us directly (you'll be
wasting your time), and do NOT post anything that contains your name, your
e-mail address, etc. Rather, compose your message, encrypt it with the
public key of BlackNet (included below), and use an anonymous remailer
chain of one or more links to post this encrypted, anonymized message in
one of the locations listed (more will be added later). Be sure to describe
what you are selling, what value you think it has, your payment terms, and,
of course, a special public key (NOT the one you use in your ordinary
business, of course!) that we can use to get back in touch with you. Then
watch the same public spaces for a reply.

(With these remailers, local PGP encryption within the remailers, the use
of special public keys, and the public postings of the encrypted messages,
a secure, two-way, untraceable, and fully anonymous channel has been opened
between the customer and BlackNet. This is the key to BlackNet.)

A more complete tutorial on using BlackNet will soon appear, in plaintext
form, in certain locations in cyberspace.

Join us in this revolutionary--and profitable--venture.


BlackNet<nowhere@cyberspace.nil>

Nightcrawler
4096R/BBF7433B 2012-09-22 Nightcrawler <Nightcrawler@SR>
PGP Key Fingerprint = D870 C6AC CC6E 46B0 E0C7  3955 B8F1 D88E BBF7 433B