Setting Key of System.Security.Cryptography.AesManaged in C# - aes

When I instantiate AesManaged in C#, it already has the .Key property set. Is it safe to use it? I.e. is it cryptographically strong and random enough for each new instantiation of AesManaged (and every time I call .GenerateKey() on an existing instance)?
All examples I've seen, first generate a random password and then use a key derivation function like Rfc2898DeriveBytes or PasswordDeriveBytes to generate the Key (e.g. How to use 'System.Security.Cryptography.AesManaged' to encrypt a byte[]?). This requires additional information - like salt value, number of password iterations, what hash algorithm to use.
I understand I need all that if I want my users to come up with passwords. I then need to produce random cryptographically strong Keys from them. But if everything is generated by the computer, do I need to programmatically generate random passwords and then Keys from them, or can I just use whatever AesManaged.Key contains?

Yes, you can use the default Key and IV values if you like. You can also explicitly regenerate a new random one with:
SymmetricAlgorithm.GenerateKey() or SymmetricAlgorithm.CreateEncryptor(null, null)
It depends on what you are protecting and how many owners of information you need to support. If speed / volume doesn't matter, then you are still better adopting PBKDF2 by using Rfc2898DeriveBytes for the iterations.
Regardless, you don't want to share the key across multiple users / tenants / security "realms", however, but sure you can use the default key for a single application. If you do, combine the salt with it.
The reasons we use user defined passwords and salts are to avoid attacks that exploit common/weak passwords or shared passwords between users and to ensure as application owners don't know their keys.
The reasons we use PBKDF2 (derivation with many iterations) is to slow down the attacker. Penalty we pay 1 time per user is paid many times by an attacker.
If your needs are just to have a random key for a single application or system, then the default is usable, assuming, of course, it provides the strength you need.

Related

decode SHA1 knowing stored value [duplicate]

Is it possible to reverse a SHA-1?
I'm thinking about using a SHA-1 to create a simple lightweight system to authenticate a small embedded system that communicates over an unencrypted connection.
Let's say that I create a sha1 like this with input from a "secret key" and spice it with a timestamp so that the SHA-1 will change all the time.
sha1("My Secret Key"+"a timestamp")
Then I include this SHA-1 in the communication and the server, which can do the same calculation. And hopefully, nobody would be able to figure out the "secret key".
But is this really true?
If you know that this is how I did it, you would know that I did put a timestamp in there and you would see the SHA-1.
Can you then use those two and figure out the "secret key"?
secret_key = bruteforce_sha1(sha1, timestamp)
Note1:
I guess you could brute force in some way, but how much work would that actually be?
Note2:
I don't plan to encrypt any data, I just would like to know who sent it.
No, you cannot reverse SHA-1, that is exactly why it is called a Secure Hash Algorithm.
What you should definitely be doing though, is include the message that is being transmitted into the hash calculation. Otherwise a man-in-the-middle could intercept the message, and use the signature (which only contains the sender's key and the timestamp) to attach it to a fake message (where it would still be valid).
And you should probably be using SHA-256 for new systems now.
sha("My Secret Key"+"a timestamp" + the whole message to be signed)
You also need to additionally transmit the timestamp in the clear, because otherwise you have no way to verify the digest (other than trying a lot of plausible timestamps).
If a brute force attack is feasible depends on the length of your secret key.
The security of your whole system would rely on this shared secret (because both sender and receiver need to know, but no one else). An attacker would try to go after the key (either but brute-force guessing or by trying to get it from your device) rather than trying to break SHA-1.
SHA-1 is a hash function that was designed to make it impractically difficult to reverse the operation. Such hash functions are often called one-way functions or cryptographic hash functions for this reason.
However, SHA-1's collision resistance was theoretically broken in 2005. This allows finding two different input that has the same hash value faster than the generic birthday attack that has 280 cost with 50% probability. In 2017, the collision attack become practicable as known as shattered.
As of 2015, NIST dropped SHA-1 for signatures. You should consider using something stronger like SHA-256 for new applications.
Jon Callas on SHA-1:
It's time to walk, but not run, to the fire exits. You don't see smoke, but the fire alarms have gone off.
The question is actually how to authenticate over an insecure session.
The standard why to do this is to use a message digest, e.g. HMAC.
You send the message plaintext as well as an accompanying hash of that message where your secret has been mixed in.
So instead of your:
sha1("My Secret Key"+"a timestamp")
You have:
msg,hmac("My Secret Key",sha(msg+msg_sequence_id))
The message sequence id is a simple counter to keep track by both parties to the number of messages they have exchanged in this 'session' - this prevents an attacker from simply replaying previous-seen messages.
This the industry standard and secure way of authenticating messages, whether they are encrypted or not.
(this is why you can't brute the hash:)
A hash is a one-way function, meaning that many inputs all produce the same output.
As you know the secret, and you can make a sensible guess as to the range of the timestamp, then you could iterate over all those timestamps, compute the hash and compare it.
Of course two or more timestamps within the range you examine might 'collide' i.e. although the timestamps are different, they generate the same hash.
So there is, fundamentally, no way to reverse the hash with any certainty.
In mathematical terms, only bijective functions have an inverse function. But hash functions are not injective as there are multiple input values that result in the same output value (collision).
So, no, hash functions can not be reversed. But you can look for such collisions.
Edit
As you want to authenticate the communication between your systems, I would suggest to use HMAC. This construct to calculate message authenticate codes can use different hash functions. You can use SHA-1, SHA-256 or whatever hash function you want.
And to authenticate the response to a specific request, I would send a nonce along with the request that needs to be used as salt to authenticate the response.
It is not entirely true that you cannot reverse SHA-1 encrypted string.
You cannot directly reverse one, but it can be done with rainbow tables.
Wikipedia:
A rainbow table is a precomputed table for reversing cryptographic hash functions, usually for cracking password hashes. Tables are usually used in recovering a plaintext password up to a certain length consisting of a limited set of characters.
Essentially, SHA-1 is only as safe as the strength of the password used. If users have long passwords with obscure combinations of characters, it is very unlikely that existing rainbow tables will have a key for the encrypted string.
You can test your encrypted SHA-1 strings here:
http://sha1.gromweb.com/
There are other rainbow tables on the internet that you can use so Google reverse SHA1.
Note that the best attacks against MD5 and SHA-1 have been about finding any two arbitrary messages m1 and m2 where h(m1) = h(m2) or finding m2 such that h(m1) = h(m2) and m1 != m2. Finding m1, given h(m1) is still computationally infeasible.
Also, you are using a MAC (message authentication code), so an attacker can't forget a message without knowing secret with one caveat - the general MAC construction that you used is susceptible to length extension attack - an attacker can in some circumstances forge a message m2|m3, h(secret, m2|m3) given m2, h(secret, m2). This is not an issue with just timestamp but it is an issue when you compute MAC over messages of arbitrary length. You could append the secret to timestamp instead of pre-pending but in general you are better off using HMAC with SHA1 digest (HMAC is just construction and can use MD5 or SHA as digest algorithms).
Finally, you are signing just the timestamp and the not the full request. An active attacker can easily attack the system especially if you have no replay protection (although even with replay protection, this flaw exists). For example, I can capture timestamp, HMAC(timestamp with secret) from one message and then use it in my own message and the server will accept it.
Best to send message, HMAC(message) with sufficiently long secret. The server can be assured of the integrity of the message and authenticity of the client.
You can depending on your threat scenario either add replay protection or note that it is not necessary since a message when replayed in entirety does not cause any problems.
Hashes are dependent on the input, and for the same input will give the same output.
So, in addition to the other answers, please keep the following in mind:
If you start the hash with the password, it is possible to pre-compute rainbow tables, and quickly add plausible timestamp values, which is much harder if you start with the timestamp.
So, rather than use
sha1("My Secret Key"+"a timestamp")
go for
sha1("a timestamp"+"My Secret Key")
I believe the accepted answer is technically right but wrong as it applies to the use case: to create & transmit tamper evident data over public/non-trusted mediums.
Because although it is technically highly-difficult to brute-force or reverse a SHA hash, when you are sending plain text "data & a hash of the data + secret" over the internet, as noted above, it is possible to intelligently get the secret after capturing enough samples of your data. Think about it - your data may be changing, but the secret key remains the same. So every time you send a new data blob out, it's a new sample to run basic cracking algorithms on. With 2 or more samples that contain different data & a hash of the data+secret, you can verify that the secret you determine is correct and not a false positive.
This scenario is similar to how Wifi crackers can crack wifi passwords after they capture enough data packets. After you gather enough data it's trivial to generate the secret key, even though you aren't technically reversing SHA1 or even SHA256. The ONLY way to ensure that your data has not been tampered with, or to verify who you are talking to on the other end, is to encrypt the entire data blob using GPG or the like (public & private keys). Hashing is, by nature, ALWAYS insecure when the data you are hashing is visible.
Practically speaking it really depends on the application and purpose of why you are hashing in the first place. If the level of security required is trivial or say you are inside of a 100% completely trusted network, then perhaps hashing would be a viable option. Hope no one on the network, or any intruder, is interested in your data. Otherwise, as far as I can determine at this time, the only other reliably viable option is key-based encryption. You can either encrypt the entire data blob or just sign it.
Note: This was one of the ways the British were able to crack the Enigma code during WW2, leading to favor the Allies.
Any thoughts on this?
SHA1 was designed to prevent recovery of the original text from the hash. However, SHA1 databases exists, that allow to lookup the common passwords by their SHA hash.
Is it possible to reverse a SHA-1?
SHA-1 was meant to be a collision-resistant hash, whose purpose is to make it hard to find distinct messages that have the same hash. It is also designed to have preimage-resistant, that is it should be hard to find a message having a prescribed hash, and second-preimage-resistant, so that it is hard to find a second message having the same hash as a prescribed message.
SHA-1's collision resistance is broken practically in 2017 by Google's team and NIST already removed the SHA-1 for signature purposes in 2015.
SHA-1 pre-image resistance, on the other hand, still exists. One should be careful about the pre-image resistance, if the input space is short, then finding the pre-image is easy. So, your secret should be at least 128-bit.
SHA-1("My Secret Key"+"a timestamp")
This is the pre-fix secret construction has an attack case known as the length extension attack on the Merkle-Damgard based hash function like SHA-1. Applied to the Flicker. One should not use this with SHA-1 or SHA-2. One can use
HMAC-SHA-256 (HMAC doesn't require the collision resistance of the hash function therefore SHA-1 and MD5 are still fine for HMAC, however, forgot about them) to achieve a better security system. HMAC has a cost of double call of the hash function. That is a weakness for time demanded systems. A note; HMAC is a beast in cryptography.
KMAC is the pre-fix secret construction from SHA-3, since SHA-3 has resistance to length extension attack, this is secure.
Use BLAKE2 with pre-fix construction and this is also secure since it has also resistance to length extension attacks. BLAKE is a really fast hash function, and now it has a parallel version BLAKE3, too (need some time for security analysis). Wireguard uses BLAKE2 as MAC.
Then I include this SHA-1 in the communication and the server, which can do the same calculation. And hopefully, nobody would be able to figure out the "secret key".
But is this really true?
If you know that this is how I did it, you would know that I did put a timestamp in there and you would see the SHA-1. Can you then use those two and figure out the "secret key"?
secret_key = bruteforce_sha1(sha1, timestamp)
You did not define the size of your secret. If your attacker knows the timestamp, then they try to look for it by searching. If we consider the collective power of the Bitcoin miners, as of 2022, they reach around ~293 double SHA-256 in a year. Therefore, you must adjust your security according to your risk. As of 2022, NIST's minimum security is 112-bit. One should consider the above 128-bit for the secret size.
Note1: I guess you could brute force in some way, but how much work would that actually be?
Given the answer above. As a special case, against the possible implementation of Grover's algorithm ( a Quantum algorithm for finding pre-images), one should use hash functions larger than 256 output size.
Note2: I don't plan to encrypt any data, I just would like to know who sent it.
This is not the way. Your construction can only work if the secret is mutually shared like a DHKE. That is the secret only known to party the sender and you. Instead of managing this, a better way is to use digital signatures to solve this issue. Besides, one will get non-repudiation, too.
Any hashing algorithm is reversible, if applied to strings of max length L. The only matter is the value of L. To assess it exactly, you could run the state of art dehashing utility, hashcat. It is optimized to get best performance of your hardware.
That's why you need long passwords, like 12 characters. Here they say for length 8 the password is dehashed (using brute force) in 24 hours (1 GPU involved). For each extra character multiply it by alphabet length (say 50). So for 9 characters you have 50 days, for 10 you have 6 years, and so on. It's definitely inaccurate, but can give us an idea, what the numbers could be.

Password hashing using CryptoKit

I'm using (CryptoKit) to use AES-GCM to encrypt some data and authenticate it as well.
However, I was wondering how I would generate an AES-GCM key from a plain text password. Normally, you would use a KDF function for that, like PBKDF2.
In CryptoKit, there is a HKDF class which does about what I want: https://developer.apple.com/documentation/cryptokit/hkdf
However, I am wondering what KDF algorithm the DeriveKey function uses. Does it use PBKDF2? Does it use bcrypt? If so, how do I specify settings, or are the settings automatically determined?
HKDF is defined in RFC5869. It is intended to generate keys from some cryptographically secure "keying material" (IKM). It is not intended for stretching a human-generated password. As discussed in section 4 Applications of HKDF:
On the other hand, it is anticipated that some applications will not
be able to use HKDF "as-is" due to specific operational requirements,
or will be able to use it but without the full benefits of the
scheme. One significant example is the derivation of cryptographic
keys from a source of low entropy, such as a user's password. The
extract step in HKDF can concentrate existing entropy but cannot
amplify entropy. In the case of password-based KDFs, a main goal is
to slow down dictionary attacks using two ingredients: a salt value,
and the intentional slowing of the key derivation computation. HKDF
naturally accommodates the use of salt; however, a slowing down
mechanism is not part of this specification. Applications interested
in a password-based KDF should consider whether, for example, [PKCS5]
meets their needs better than HKDF.
I don't believe that CryptoKit offers a PBKDF of any kind (PBKDF2, scrypt, bcrypt, argon2). It's a very limited framework (I have yet to find a situation where it was useful). You will likely need to continue to use CommonCrypto for this, or implement it yourself (or use something like CryptoSwift, which I believe implements several).

Separate data encryption

I store some sensitive data. Data is divded into parts and I want to have separate accees to each part. Let's assume that I have 1000 files. I want to encrypt each file by the same symetric encryption algorithm.
I guess that breaking a key is easier when hacker has got 1000 cryptogram than he has only one cryptogram, so I think that I should use separate key for each file.
My question is following:
Should I use separate key for each file?
If I should, there is problem with storing 1000 keys. So I want to have one secret key and use some my own algorithm to calculate separate key for each file from secret key. Is it good idea?
If you consider passive adversary and use CPA-strong cipher (like AES), it is sufficient to use only one key for all files. Supposing adversary knows the cipher you use, and even knows plaintexts, he cannot reconstruct the key with non-negligible probability. Here is more detailed answer.
If you consider also active adversary (which can replace ciphertexts) you should use Authenticated Encryption. But as I understand this is not your case.
So I want to have one secret key and use some my own algorithm to calculate separate key for each file from secret key. Is it good idea?
In general, developing your own algorithm or scheme is bad idea. You can easily make some unseen mistake in algorithm or implementation and you data will be vulnerable. It is better to use well-known algorithms and implementations peer-reviewed by lots of people and proved to be secure.

How practical would it be to repeatedly encrypt a given file?

I'm currently experimenting with both public-key and personal file encryption. The programs I use have 2048 bit RSA and 256 bit AES level encryption respectively. As a newbie to this stuff (I've only been a cypherpunk for about a month now - and am a little new to information systems) I'm not familiar with RSA algorithms, but that's not relevant here.
I know that unless some secret lab or NSA program happens to have a quantum computer, it is currently impossible to brute force hack the level of security these programs provide, but I was wondering how much more secure it would be to encrypt a file over and over again.
In a nutshell, what I would like to know is this:
When I encrypt a file using 256-bit AES, and then encrypt the already encrypted file once more (using 256 again), do I now have the equivalent of 512-bit AES security? This is pretty much a question of whether or not the the number of possible keys a brute force method would potentially have to test would be 2 x 2 to the 256th power or 2 to the 256th power squared. Being pessimistic, I think it is the former but I was wondering if 512-AES really is achievable by simply encrypting with 256-AES twice?
Once a file is encrypted several times so that you must keep using different keys or keep putting in passwords at each level of encryption, would someone** even recognize if they have gotten through the first level of encryption? I was thinking that perhaps - if one were to encrypt a file several times requiring several different passwords - a cracker would not have any way of knowing if they have even broken through the first level of encryption since all they would have would still be an encrypted file.
Here's an example:
Decrypted file
DKE$jptid UiWe
oxfialehv u%uk
Pretend for a moment that the last sequence is what a cracker had to work with - to brute-force their way back to the original file, the result they would have to get (prior to cracking through the next level of encryption) would still appear to be a totally useless file (the second line) once they break through the first level of encryption. Does this mean that anyone attempting to use brute-force would have no way of getting back to the original file since they presumably would still see nothing but encrypted files?
These are basically two questions that deal with the same thing: the effect of encrypting the same file over and over again. I have searched the web to find out what effect repeated encryption has on making a file secure, but aside from reading an anecdote somewhere that the answer to the first question is no, I have found nothing that pertains to the second spin on the same topic. I am especially curious about that last question.
**Assuming hypothetically that they somehow brute-forced their way through weak passwords - since this appears to be a technological possibility with 256-AES right now if you know how to make secure ones...
In general, if you encrypt a file with k-bit AES then again with k-bit AES, you only get (k+1) bits of security, rather than 2k bits of security, with a man-in-the-middle attack. The same holds for most types of encryption, like DES. (Note that triple-DES is not simply three rounds of encryption for this reason.)
Further, encrypting a file with method A and then with method B need not be even as strong as encrypting with method B alone! (This would rarely be the case unless method A is seriously flawed, though.) In contrast, you are guaranteed to be at least as strong as method A. (Anyone remembering the name of this theorem is encouraged to leave a comment; I've forgotten.)
Usually you're much better off simply choosing a single method as strong as possible.
For your second question: Yes, with most methods, an attacker would know that the first layer had been compromised.
More an opinion here...
First, when computer are strong enough to do a brute-force attack on AES-256 for example, it will be also for iterations of the same... doubling or tripling the time or effort is insignificant at that level.
Next, such considerations can be void depending on the application you are trying to use this encryption in... The "secrets" you will need to carry become bigger (number of iterations and all the different keys you will need, if in fact they are different), the time to do the encryption and the decryption will also need to increase.
My hunch is that iterating the encryption does not help much. Either the algorithm is strong enough to sustain a brute-force attach or it is not. The rest is all in the protection of the keys.
More practically, do you think your house is more protected if you have three identical or similar locks on your front door ? (and that includes number of keys for you to carry around, don't loose those keys, make sure windows and back door are secured also...)
Question 1:
The size of the solution space is going to be the same for two passes of the 256-bit key as the 512-bit key, since 2^(256+256) = 2^512
The actual running time of each decrypt() may increase non-linearly as the key-size grows (it would depend on the algorithm), in this case I think brute forcing the 256+256 would run faster than the 2^512, but would still be infeasible.
Question 2:
There are probably ways to identify certain ciphertext. I wouldn't be surprised if many algorithms leave some signature or artifacts that could be used for identification.

Am I misunderstanding what a hash salt is?

I am working on adding hash digest generating functionality to our code base. I wanted to use a String as a hash salt so that a pre-known key/passphrase could be prepended to whatever it was that needed to be hashed. Am I misunderstanding this concept?
A salt is a random element which is added to the input of a cryptographic function, with the goal of impacting the processing and output in a distinct way upon each invocation. The salt, as opposed to a "key", is not meant to be confidential.
One century ago, cryptographic methods for encryption or authentication were "secret". Then, with the advent of computers, people realized that keeping a method completely secret was difficult, because this meant keeping software itself confidential. Something which is regularly written to a disk, or incarnated as some dedicated hardware, has trouble being kept confidential. So the researchers split the "method" into two distinct concepts: the algorithm (which is public and becomes software and hardware) and the key (a parameter to the algorithm, present in volatile RAM only during processing). The key concentrates the secret and is pure data. When the key is stored in the brain of a human being, it is often called a "password" because humans are better at memorizing words than bits.
Then the key itself was split later on. It turned out that, for proper cryptographic security, we needed two things: a confidential parameter, and a variable parameter. Basically, reusing the same key for distinct usages tends to create trouble; it often leaks information. In some cases (especially stream ciphers, but also for hashing passwords), it leaks too much and leads to successful attacks. So there is often a need for variability, something which changes every time the cryptographic method runs. Now the good part is that most of the time, variability and secret need not be merged. That is, we can separate the confidential from the variable. So the key was split into:
the secret key, often called "the key";
a variable element, usually chosen at random, and called "salt" or "IV" (as "Initial Value") depending on the algorithm type.
Only the key needs to be secret. The variable element needs to be known by all involved parties but it can be public. This is a blessing because sharing a secret key is difficult; systems used to distribute such a secret would find it expensive to accommodate a variable part which changes every time the algorithm runs.
In the context of storing hashed passwords, the explanation above becomes the following:
"Reusing the key" means that two users happen to choose the same password. If passwords are simply hashed, then both users will get the same hash value, and this will show. Here is the leakage.
Similarly, without a hash, an attacker could use precomputed tables for fast lookup; he could also attack thousands of passwords in parallel. This still uses the same leak, only in a way which demonstrates why this leak is bad.
Salting means adding some variable data to the hash function input. That variable data is the salt. The point of the salt is that two distinct users should use, as much as possible, distinct salts. But password verifiers need to be able to recompute the same hash from the password, hence they must have access to the salt.
Since the salt must be accessible to verifiers but needs not be secret, it is customary to store the salt value along with the hash value. For instance, on a Linux system, I may use this command:
openssl passwd -1 -salt "zap" "blah"
This computes a hashed password, with the hash function MD5, suitable for usage in the /etc/password or /etc/shadow file, for the password "blah" and the salt "zap" (here, I choose the salt explicitly, but under practical conditions it should be selected randomly). The output is then:
$1$zap$t3KZajBWMA7dVxwut6y921
in which the dollar signs serve as separators. The initial "1" identifies the hashing method (MD5). The salt is in there, in cleartext notation. The last part is the hash function output.
There is a specification (somewhere) on how the salt and password are sent as input to the hash function (at least in the glibc source code, possibly elsewhere).
Edit: in a "login-and-password" user authentication system, the "login" could act as a passable salt (two distinct users will have distinct logins) but this does not capture the situation of a given user changing his password (whether the new password is identical to an older password will leak).
You are understanding the concept perfectly. Just make sure the prepended salt is repeatable each and every time.
If I'm understanding you correctly, it sounds like you've got it right. The psuedocode for the process looks something like:
string saltedValue = plainTextValue + saltString;
// or string saltedalue = saltString + plainTextValue;
Hash(saltedValue);
The Salt just adds another level of complexity for people trying to get at your information.
And it's even better if the salt is different for each encrypted phrase since each salt requires its own rainbow table.
Its worth mentioning that even though the salt should be different for each password usage, your salt should in NO WAY be computed FROM the password itself! This sort of thing has the practical upshot of completely invalidating your security.