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The case of the 9 bit AES key(v12.sh)
132 points by ledoge 1 day ago | 68 comments
[–] philsnow 22 hours ago
It's so insane to have PDF programs doing their own encryption, not because "don't roll your own crypto" (although yes for that reason too), but because the people who write PDF programs (libraries, viewers, general-purpose tools like qpdf, etc etc) aren't (necessarily) going to be great at understanding or designing good encryption UX.

Also, I get that a lot of sensitive information is exchanged with PDFs these days, but why should PDFs have encryption built-in to the file format? Sensitive information is also exchanged in image files, word documents, zip files, html, etc etc etc etc. If you take all the work that goes into making the crypto UX decent for one kind of file and apply that to "all files", then each ecosystem doesn't have to invent their own.

This is just like "high-end" car manufacturers insisting on making their own software, and not integrating apple carplay. They're either going to make a truly shitty podcast app, or they're not even going to bother and instead tell people to use bluetooth to listen to podcasts like it's 2006.

[–] dingaling 19 hours ago
> but why should PDFs have encryption built-in to the file format?

Because very few 'end user' people know how to use en/decryption. So it's much easier to send them a familiar file and say 'enter this password' than to have them searching the web to work out which arguments to pass to openssl. In a command line? What's that?

I received an AES-encrypted file recently but neither gnupg nor openssl could determine what mode and keysettings the sender had used, so it was just a useless lump of data. Very secure though...

[–] 1718627440 12 minutes ago
This should simply be an option in the context menu of the file manager. (And is on my Linux machine)
[–] lmz 20 hours ago
Usually the desire is for some of the metadata processing to be reusable between the encrypted and non encrypted formats ("like a regular file, just this data is encrypted"). This is also why eg. Zip files are encrypted per entry, not globally.

Since the kind of data people want available may differ for each file format, here we are.

[–] otabdeveloper4 14 hours ago
> but why should PDFs have encryption built-in to the file format?

So you could open encrypted documents on iOS and Android.

[–] GoblinSlayer 20 hours ago
S/MIME?
[–] Avamander 12 hours ago
CDOC2, there are also other similar widely used encrypted container formats.
[–] tptacek 1 day ago
"MuPDF versions before 1.28.5 use an implementation of the drand48 family" yeah, ok, so they're basically not doing real encryption. The number of bits in the key space isn't the real story; the keys simply aren't cryptographically random.
[–] somat 1 day ago
You could do what openbsd did and tie all the traditional weak psudorandom interfaces into a cryptographically secure one. it will still match the drand48() interface. I still don't think I would use them for secure things but now rand() is actually random. http://man.openbsd.org/drand48

Another pet peeve is when people use the rand() when they want hash() but I will leave that rant for another day.

[–] hansvm 1 day ago
I'm interested in that rant (at $WORK we adopted hash() for almost everything, and I'm curious to hear other perspectives).
[–] somat 15 hours ago
In my mind rand() (and friends) and hash(thing) (and friends) are almost the same function, with a very similar set of features required, the main difference is that rand() is non-deterministic and hash() is deterministic.

They are so close that people can and often do build rand() as "internal state s = hash(s) return s" (or similar). then other people, wanting that deterministic hash() behavior thus accidentally exposed, build entire worlds(literally) out of rand().

Another problem with this is that the rand() internals are opaque and unknown and can change without violating the spec. hash(), because it is supposed to be deterministic, usually has an exposed stable algorithm.

A specific example. At one job I found they were storing long term customer order archives encrypted where the key was a hash of the date, this in itself is a little suspicious but the archives were offline and physically locked up on site, so not too bad. The real wtf was that the encryption was done on a win98 machine with a perl script that was basically "seed(date); key = rand(); encrypt(data, key)". expecting to regenerate the key if they ever wanted to look at the data. When I saw that I went "I don't know much about perl, but that does not feel stable" and did a few checks. Sure enough the behavior of rand() could change depending on the operating system or even version. making the keys highly dependent on that exact win98 machine with that exact version of perl, I think they ended up using that machine to generate and store all used keys in a database so other machines could decrypt the archives.

[–] lo0dot0 10 hours ago
Encrypted with a key that is a date can be broken by iterating likely dates. Did they add the time up to milliseconds into it or just the date? Not sure if it matters
[–] aidenn0 23 hours ago
Per the manpage you linked, openbsd's behavior does not match the drand48() interface, since the drand48() interface requires determinism.
[–] NelsonMinar 1 day ago
What is wrong with software engineers that we keep making really stupid basic mistakes like this? Sometimes I think programming should require licensing and regular testing.
[–] anonymous908213 1 day ago
We direly need to split things into a licensed engineering field which is necessary for working on security- and reliability-critical systems, and a generic unlicensed software developer field where people can screw around with their 1000 dependency JS frontends to their hearts' content. The two should not be conflated and yet so easily are.
[–] greggsy 1 day ago
Certification do exist for engineers, and various industries and governments impose their own certification programs on platforms and software before they’re authorised for use.

Each with varying degrees of trust. The outcome is never perfect, but that’s not their purpose.

[–] nyargh 21 hours ago
Credentialism is not a solution, it will just get gamed too. Indian diploma mills and mega IT consultancies pump out thousands of "qualified" engineers every year.

Every hiring manager worth their salt has caught at least one completely incompetent applicant with a CV full of certifications.

[–] GoblinSlayer 17 hours ago
Maybe certifications are different? A certified Electron engineer might just read the tutorial how to spend zero effort on apps.
[–] asveikau 21 hours ago
One of the problems with cryptography implementations is that a bad one will be indistinguishable from a good one on the surface level. Totally broken crypto will superficially look and work as if it it works, and most people won't look deeply. This has been commented upon for years.
[–] LeoPanthera 1 day ago
This is partly why I'm not too worried about AI slopcode.

The human bar is not that high.

I would much rather have rigorous testing than a filter based on the origin of the code.

[–] hansvm 1 day ago
What's your method for implementing rigorous testing while using AI?
[–] nyargh 21 hours ago
Testing doesn't even need to be that rigorous for humans, it's easy to spot someone who is lying about the depth of their experience with a 15 minute conversation.

For AI this will be impossible, however.

If you're talking about testing of code, well "tests can only prove the presence of bugs, not their absence"

[–] rsalus 1 day ago
I think it's safe to assume anything associated with PDFs is radioactive.
[–] HackerThemAll 1 day ago
Those are not the "software engineers" but coders, those who like to say that the university degree doesn't add anything in programming.
[–] anonymous908213 1 day ago
University degrees are not the difference between an engineer and a developer, universities have churned out millions of people who don't care about programming and have no idea what they're doing, who are just following the script with as little effort as possible because they were told it was the easiest way to make a lot of money.
[–] adrianN 1 day ago
You can get through a Computer Science degree with just a few thousand lines of code if you focus on theory courses.
[–] thin_carapace 1 day ago
a small wonder the wunderkinds of computer science were at all capable given their lack of computer science degrees
[–] gsich 1 day ago
one and the same
[–] jburgess777 1 day ago
Does the DMCA still make it illegal to access encrypted content no matter how easy it is to discover the key? https://www.law.cornell.edu/uscode/text/17/1201

Would the new LLM model owners like to strike this down, or use it to demonstrate how dangerous unrestricted models can be?

[–] nextaccountic 23 hours ago
there is a case to be made that weak encryption is equivalent to no encryption at all
[–] leni536 20 hours ago
Pdfium powers Chrome's/Chromium's PDF viewer, but maybe Chrome doesn't expose encrypting PDF documents as a feature to be affected?
[–] exabrial 7 hours ago
String.getBytes(UTF-8) is an incredibly common way to kneecap yourself

always Base64Encode/Decode!

[–] ubutler 1 day ago
Rule #1 of rolling your own RNG: don’t.

Rule #2? Please don’t.

[–] Mikhail_Edoshin 19 hours ago
This translates into "trust some authority", which is also a task. And it does not work when the canned solution does not quite fit, e. g. involves a bulky lib. The true answer should be "use your software engineering textbook and the standard reference of RNGs". Thing is, there is no such reference.
[–] 1718627440 9 minutes ago
> Thing is, there is no such reference.

man encrypt works. info /encrypt works too.

[–] mik1998 18 hours ago
Handbook of Applied Cryptography is a good reference for implementing classic cryptographic algorythms.
[–] j16sdiz 1 day ago
That's why we use the system RNG !
[–] cowlevel 1 day ago
Be careful to use the cryptographic one, not rand(3)

And if you're a sysadmin, be extremely careful when generating keys in VMs or embedded devices. They tend to overestimate their entropy sources - it's possible that every clone of a VM generates the same keys. In some cases (cough ECDSA) generating the same key and nonce to sign two different messages is catastrophic - it immediately leaks the private key.

[–] saidnooneever 1 day ago
good point about VMs. if you run some VPS your provider could just link in a shitty rng into the thing and not give access to the correct hardware rng. U'd really need to dig into that to find out :/.

-object rng-random,id=objrng0,filename=/dev/null

or maybe just a file that contains 4 :O

[–] Novosell 1 day ago
As long as the 4 is random!
[–] saidnooneever 20 hours ago
cat /dev/random | grep 4
[–] flanz_10 1 day ago
btw, the idea that the system rng isnt good enough, or "runs out" or whatever, is no longer true on pretty much every modern, widely used os.

btw... im sure there's some legacy rng in windows or some shit that isnt good. read the docs but if it's the blessed system rng, you're probably fine!

although... i suppose if this is news to you (the person reading this), then you probably shouldn't be implementing whatever you are that really requires prng. ask a friend for help. im not trying to be a jerk, i just want to make sure you dont hurt yourself!

[–] ahartmetz 1 day ago
Rule 3: Use as many bits of randomness as the key size.

Rule 3b: Failing rule 3, disclose motivations and full list of employers and / or customers

[–] timerol 1 day ago
Rule 3c: At least as many bits. Bits tend to not be as random as you think they are
[–] snvzz 1 day ago
That's way too many PDF implementations affected by this category of stupidity.

It makes me wonder: Coincidence, really? There's enough there to think that there might be some invisible hand behind it.

[–] JonChesterfield 1 day ago
Wonderful.
[–] paulpauper 1 day ago
it's like the weak hardware wallet entropy bug
[–] esafak 1 day ago
I assume this is the fruit of AI-driven decompilation? Nice work.
[–] jeffbee 1 day ago
You'd have to be completely off your rocker to use a PDF tool written in C anyway.
[–] advisedwang 1 day ago
very VERY few people judge tools like this by the language used to develop them.
[–] jeffbee 1 day ago
How many people judge their tools based on the AES key entropy?
[–] OptionX 1 day ago
A lot actually.

You're confusing just assuming by default its enough for purpose rather than not caring at all.

[–] j16sdiz 1 day ago
just down vote it.

You can downvote anything not interesting.

If he have list some alternative or give example, it might be interesting.

[–] cowlevel 1 day ago
What are the alternatives?
[–] crote 1 day ago
PDF.js, for example. It's what Firefox uses, and most websites with integrated on-page PDF viewing functionality.
[–] lirolero 1 day ago
Genuine question, since I'm not very knowledgeable about this: why is using C for a PDF tool such a bad idea?
[–] zamalek 1 day ago
File formats are the buffer issue honeypot. You may be aware of how often video and audio codecs have vulnerabilities - it's nearly never the hand-tuned frame decode assembly (where you would think all the mistakes would be). It's nearly always the thing that reads the metadata and encoded frames to memory. Binary formats have things like offsets in them, and those can be trivially used to overrun.

Same thing applies here. Even Rust has a crate for dealing with binary data, despite its memory promises: https://crates.io/crates/untrusted

It's a fucking minefield, and this is one area where the Rust zealots are undeniably correct. It doesn't have to be Rust, any memory safe language will do, but Rust also happens to be performance competitive and that's usually also desirable.

[–] tialaramex 1 day ago
The technology you want for this sort of work is WUFFS, for Wrangling Untrusted File Formats Safely.

Rust is a general purpose programming language, which is great if your problem might be something never imagined before, but this literally isn't our first rodeo, we have wrangled lots of file formats before, we should use a language purpose-built to do that safely.

[–] zamalek 1 day ago
> Rust is a general purpose programming language

I don't understand how I hit the anti-Rust tripwire here:

> My comment: any memory safe language will do

[–] tialaramex 1 day ago
Not an anti-Rust tripwire. Just that WUFFS is the appropriate technology.

I like 4th edition D&D but if you're trying to make a story about nuanced inter-personal conflict in which there's no actual violence it's just not the right roleplaying system and so I'm not going to agree with your choice to recommend 4eD&D as the system for the story "Love and Jealousy in the Elven Forest"

I've written a whole bunch of Rust, and hardly any WUFFS - but, I wasn't writing code for Wrangling Untrusted File Formats and that's very much what you're doing in a PDF parser.

[–] jeffbee 1 day ago
I am a big fan of WUFFS but some recent developments by people assisted by AIs writing format parsers in other languages has made me question whether it will be maintained or forgotten.
[–] tptacek 1 day ago
I think the claim is hyperbolic, since most people memory-unsafe PDF implementations, but PDF is a monster format, a metaformat that brings in virtually every conceivable display format, and their renderer implementations with them, often poorly-maintained, never-touched reference implementations from the before times. PDF is pretty scary.
[–] DonHopkins 7 hours ago
Plus the PDF file name extension has been co-opted as a censorship-safe shorthand for Donald Trump and the Epstein Class he's protecting. Adobe must be totally pissed off about that.

You're right, PDFs are horrible scary monsters who you should never trust.

[–] cowlevel 1 day ago
PDFs are usually untrusted input and C provides no assurance there isn't a bug in the code that allows corrupted input to turn into arbitrary remote code execution.
[–] F3nd0 1 day ago
Other than Ada/SPARK, which languages can guarantee this won’t happen?
[–] cowlevel 1 day ago
Very few languages can prevent you writing something like "if(text == "shibboleth") rootshell();" but most languages don't make it trivial to write accidentally.
[–] mahemm 8 hours ago
Pretty much any memory managed language? Java, Go, Rust, Python, pretty much anything other than C/C++ these days is memory safe for security purposes.
[–] tialaramex 1 day ago
This trivially can't happen in WUFFS. Forget RCE, WUFFS can't even do a traditional Hello World program because (1) you can't do I/O in WUFFS and (2) the language doesn't have strings.

https://github.com/google/wuffs

[–] recursive 1 day ago
buffer overflow vulnerability in code dealing with user generated data and a complex file format.