CRAM-MD5 Implementation - encryption

I'm looking at implementing CRAM-MD5 authentication for an IMAP and SMTP server. Problem is that CRAM seems to require a clear text password to be available at all times. The server sends the client a unique challenge and the client returns:
MD5( MD5(password, challenge), MD5( password ) )
I can't see a way to check this without having a clear text password, the specification doesn't say it has to have one available but it only seems logical.
The only solution I can come up with is to encrypt (properly encrypt, not hash) the password into the database (probably using RSA key based AES, as I already have something to deal with that) and decrypt it when I need to compare, seems a very slow way around though as it will need decrypting and hashing for every single login on SMTP and IMAP.
Is this the best solution / most efficient solution?
Or, better, is CRAM out-of-date now because even less secure authentication over the wire is secured with SSL now?

the trick is that all you really need is the unfinalized md5 of the password which is the same as the intermediate state of the md5 context before finalizing.
MD5_CTX ctx;
MD5Init(&ctx);
MD5Update(&ctx, password, length);
if you do this and then store the value of ctx as hashed, then one can then use copies of it in CRAM MD5 like this
for MD5(password, challenge)
MD5Update(&hashed, challenge, length);
MD5Final(&digest, &hashed);
and for MD5( password )
MD5Final(&digest, &hashed);
the rest of MD5( MD5(password, challenge), MD5( password ) ) is rather simple
i would have liked to use python for this example but in the standard md5 there is no way to get access to the state of a md5 object so i used libmd5's api

There is currently a draft RFC proposing to move DIGEST-MD5 to historical status, CRAM MD5 isn't in a much better state either.
If you want proper security, start with TLS and SASL - in that mode, PLAIN is considered acceptable, but, if as far as you're concerned it's not satisfactory, then I would recommend implementing GSSAPI or NTLM on top of it.

The sources for Python of hashlib.py say that you can initialize a hash instance with binary data but from the usage it seems to mean "initialize with the hash of this data".
However, you can clone the object with it's internal state intact, so you could pickle the object and store that in lieu of the password. To get the password MD5, unpickle the object, and to get the challenge hash, unpickle it and call it's update() method with the challenge data.

Related

Is HMAC still needed if encrypted data is always saved and retrieved locally

My understanding of HMAC is that it can help to verify the integrity of encrypted data before the data is processed i.e. it can be used to determine whether or not the data being sent to a decryption routine has been modified in any way.
That being the case, is there any advantage in incorporating it into an encryption scheme if the data is never transmitted outside of the application generating it? My use case is quite simple - a user submits data (in plaintext) to the scripts I've written to store customer details. My scripts then encrypt this data and save it to the database, and my scripts then provide a way for the user to retrieve the data and decrypt it based on the record ID they supply. There is no way for my users to send encrypted data directly to the decryption routine and I don't need to provide an external API.
Therefore, is it reasonable to assume that there is a chain of trust in the application by default because the same application is responsible for writing and retrieving the data? If I add HMAC to this scheme, is it redundant in this context or is it best practice to always implement HMAC regardless of the context? I'm intending to use the Defuse library but I'd like to understand what the benefit of HMAC is to my project.
Thanks in advance for any advice or input :)
First, you should understand that there are attacks that allow an attacker to modify encrypted data without decrypting it. See Is there an attack that can modify ciphertext while still allowing it to be decrypted? on Security.SE and Malleability attacks against encryption without authentication on Crypto.SE. If an attacker gets write access to the encrypted data -- even without any decryption keys -- they could cause significant havoc.
You say that the encrypted data is "never transmitted outside of the application generating it" but in the next two sentences you say that you "save it to the database" which appears (to me) to be something of a contradiction. Trusting the processing of encrypted data in memory is one thing, but trusting its serialization to disk, especially if done by another program (such as a database system) and/or on a separate physical machine (now or in the future, as the system evolves).
The significant question here is: would it ever be a possible for an attacker to modify or replace the encrypted data with alternate encrypted data, without access to the application and keys? If the attacker is an insider and runs the program as a normal user, then it's not generally possible to defend your data: anything the program allows the attacker to do is on the table. However, HMAC is relevant when write access to the data is possible for a non-user (or for a user in excess of their normal permissions). If the database is compromised, an attacker could possibly modify data with impunity, even without access to the application itself. Using HMAC verification severely limits the attacker's ability to modify the data usefully, even if they get write access.
My OCD usually dictates that implementing HMAC is always good practice, if for no other reason, to remove the warning from logs.
In your case I do not believe there is a defined upside to implementing HMAC other than ensuring the integrity of the plain text submission. Your script may encrypt the data but it would not be useful in the unlikely event that bad data is passed to it.

Hashing, encrypting or both

Recently I have been looking to add some security to a project. I have been doing lots of research into the situation and discovered that clearly password hashing is a must. Further I have concluded that the best options are to use bcrypt, PBKDF2 or scrypt.
Also I have seen much discussion over hashing vs encryption and discovered that it is clear that hashing is more important. That said, after many searches into the depths of Google I have yet to find any information on whether encrypting an already properly hashed password is of any benefit, serves to harm or is relatively neutral.
Is the CPU cost of doing both worth it? Are there any pitfalls?
Encrypting something leads to the need of decrypting, which in turn leads to the problem you already have: secure storage of a secret.
Assuming that you want to store passwords as hashes instead of plain text you are basically doing this:
hashpw := hash(salt + password)
You then store salt and hashpw in a file and use this data instead of the plain text passwords. (Note that the order of the concatenation of salt and password is crucial in many cases and that this is only a visualization of the process, nothing more; Use a tool to generate salted hashes).
A possible attacker then needs to guess the salt and the plain text password to check for a match with
the stored hashpw, which is as secure as the hash algorithm you're using (rate of collisions).
Encrypting something using some cipher has the benefit of being able to restore the plain text, which
the hashing way does not offer. It also requires the system which decrypt the cipher text to have the
key available. Say you encrypt a string foo with some key bar. To decrypt the resulting cipher text
brn you need the key bar again. This key needs secure storage on your system and if the key is exposed
to the attacker, all security is gone.
As a general rule of thumb I would say that hashing provides a good way of storing texts which are
checked against (e.g., passwords) as the security of that is determined by the collision rate of the
hashing algorithm. Encryption on the other hand, is the technique you're using to store the rest of
the data securely.
You're on the right track. Use a key derivation/password hashing function like the ones you've mentioned.
Do not use just a hash or salted hash. The main issue is that traditional hashing algorithms (MD5, SHA-*, etc.) are intended to be fast. That's not advantageous for password storage, and many implementations are breakable, even if you add a salt.
Encryption always introduces key management-related issues. It should be avoided for password storage.
The advantage of a KDF is the work factor. It's designed to be slow and computationally expensive, which is why they're idea for this situation. Scrypt is the most resilient of the options you're looking at since it requires a set amount of memory to execute. This kills the GPU attack vector. There are tradeoffs whichever way you go, but all of your choices are fine as long as you use appropriate work factors where they're configurable.
I would simply encrypt the password. Hashing is fast, but a little unsafe for passwords. When I use hashing for security purposes, it's usually for things like message signing e.g. message + hash(message+password) so that the message can be verified, but I'm no expert in the field. I don't see the point of doing both.

Client side encryption - best practice

I wrote a "Password Locker" C# app a while ago as an exercise in encryption. I'd like to move the data to the web so that I can access it anywhere without compromising my password data. I'd just like to run my ideas by the community to ensure I'm not making a mistake as I'm not an encryption expert.
Here's what I envision:
In the C# app all the password data is encrypted as a single chunk of text using a user supplied password. I'm using Rijndael (symmetric encryption) in CBC mode. The password is salted using a hard coded value.
Encrypted data gets sent to my database
I go to a web page on my server and download the encrypted text. Using client side javascript I input my password. The javascript will decrypt everything (still client side)
Here are my assumptions:
I assume that all transmissions can be intercepted
I assume that the javascript (which contains the decryption algo, and hard coded salt) can be intercepted (since it's really just on the web)
The password cannot be intercepted (since it's only input client side)
The result is that someone snooping could have everything except the password.
So, based on those assumptions: Is my data safe? I realize that my data is only as safe as the strength of my password... Is there something I can do to improve that? Is Rijndael decryption slow enough to prevent brute force attacks?
I thought about using a random salt value, but that would still need to be transmitted and because of that, it doesn't seem like it would be any safer. My preference is to not store the password in any form (hashed or otherwise) on the web.
Edit:
I am considering using SSL, so my "interception" assumptions may not be valid in that case.
Edit 2:
Based on comments from Joachim Isaksson, I will be running with SSL. Please continue breaking apart my assumptions!
Edit 3:
Based on comments from Nemo I will use salt on a per user basis. Also, I'm using PBKDF2 to derive a key based on passwords, so this is where I'll get my "slowness" to resist brute force attacks.
Without even going into the crypto analysis in any way, if you're assuming all your information can be intercepted (ie you're running without SSL), you're not secure.
Since anyone can intercept the Javascript, they can also change the Javascript to make the browser pass the clear text elsewhere once decrypted.
Also, anyone hacking into the site (or the site owner) can maliciously change the Javascript to do the same thing even if SSL is on.
By "password data", I assume you mean "password-protected data"?
The salt does need to be random. It is fine that is transmitted in the clear. The purpose of a salt is protection against dictionary attacks. That is, should someone manage to obtain your entire encrypted database, they could quickly try a large dictionary of passwords against all of your users. With random salts, they need to try the dictionary against each user.
Or, alternatively, even without compromising the database, they could generate a huge collection of pre-encrypted data for lots of dictionary words, and immediately be able to recognize any known plaintext encrypted by any of those keys.
Even with a salt, dictionary attacks can be faster than you would like, so deriving key data from a password is a lot more subtle than most people realize.
Bottom line: As always, never invent your own cryptography, not even your own modes of operation. To derive an encryption key from a password, use a well-known standard like PBKDF2 (aka. PKCS#5).
Well, as this is an open question:
Issue #1
What are you going to do if the password that is supplied is incorrect, or if the salt/ciphertext is altered? You will get an incorrect decryption result, but how are you going to test that? What happens if just the last part of the ciphertext is altered? Or removed altogether?
Solution: Provide integrity protection against such attacks. Add a HMAC using a different key or use a mode like GCM mode.
Issue #2
What happens if you change or add a few bytes to the password (compare the encrypted store in time)?
Solution: Encrypt your key store with a different IV each time.
That's already 4 issues found :) Cryptography is hard.

In JDK 1.4 API, how do I encrypt a user password that the user entered in a text box?

I need to encrypt the password the user enters in a text box on the UI, save it, and then decrypt it when the getPassword() method is called.
What is the correct JDK 1.4 API I should use?
Thanks in advance.
If you want to secure you passwords, you'll may want to use a Hash algorithm like MD5 or SHA1. You don't want to decrypt the stored password to compare it with the one provided on a login but rather hash the provided password and compare the Hashs
here some documentation on the methods you can use to hash :
https://www.owasp.org/index.php/Hashing_Java
There's an example here using Java 1.4 Crypto interface for MD5 encryption:
http://download.oracle.com/javase/1.4.2/docs/guide/security/jce/JCERefGuide.html#HmacEx
Blowfish:
http://download.oracle.com/javase/1.4.2/docs/guide/security/jce/JCERefGuide.html#BlowKeyEx
Just use Cipher with the "AES/CBC/PKCS5Padding" mechanism (in getInstance()). You can use a 128 bit (16 byte) AES key created using SecretKeySpec (this is already a key!). Higher bitrates will require unlimited encryption policy files to be installed. As I noted as remark, please note that this is only obscuring the data, since the key will need to be stored with the application - so people that know what to do can retrieve both the password and key and decrypt the information outside of the application.
If you store multiple passwords with the same key, make sure you generate and store a separate random IV per password. The advise in this last paragraph is more to let you know how to encrypt stuff correctly since it is easier to obtain the key than to decrypt the data without it anyway.

How to implement password protection for individual files?

I'm writing a little desktop app that should be able to encrypt a data file and protect it with a password (i.e. one must enter the correct password to decrypt). I want the encrypted data file to be self-contained and portable, so the authentication has to be embedded in the file (or so I assume).
I have a strategy that appears workable and seems logical based on what I know (which is probably just enough to be dangerous), but I have no idea if it's actually a good design or not. So tell me: is this crazy? Is there a better/best way to do it?
Step 1: User enters plain-text password, e.g. "MyDifficultPassword"
Step 2: App hashes the user-password and uses that value as the symmetric key to encrypt/decrypt the data file. e.g. "MyDifficultPassword" --> "HashedUserPwdAndKey".
Step 3: App hashes the hashed value from step 2 and saves the new value in the data file header (i.e. the unencrypted part of the data file) and uses that value to validate the user's password. e.g. "HashedUserPwdAndKey" --> "HashedValueForAuthentication"
Basically I'm extrapolating from the common way to implement web-site passwords (when you're not using OpenID, that is), which is to store the (salted) hash of the user's password in your DB and never save the actual password. But since I use the hashed user password for the symmetric encryption key, I can't use the same value for authentication. So I hash it again, basically treating it just like another password, and save the doubly-hashed value in the data file. That way, I can take the file to another PC and decrypt it by simply entering my password.
So is this design reasonably secure, or hopelessly naive, or somewhere in between? Thanks!
EDIT: clarification and follow-up question re: Salt.
I thought the salt had to be kept secret to be useful, but your answers and links imply this is not the case. For example, this spec linked by erickson (below) says:
Thus, password-based key derivation as defined here is a function of a password, a salt, and an iteration count, where the latter two quantities need not be kept secret.
Does this mean that I could store the salt value in the same place/file as the hashed key and still be more secure than if I used no salt at all when hashing? How does that work?
A little more context: the encrypted file isn't meant to be shared with or decrypted by others, it's really single-user data. But I'd like to deploy it in a shared environment on computers I don't fully control (e.g. at work) and be able to migrate/move the data by simply copying the file (so I can use it at home, on different workstations, etc.).
Key Generation
I would recommend using a recognized algorithm such as PBKDF2 defined in PKCS #5 version 2.0 to generate a key from your password. It's similar to the algorithm you outline, but is capable of generating longer symmetric keys for use with AES. You should be able to find an open-source library that implements PBE key generators for different algorithms.
File Format
You might also consider using the Cryptographic Message Syntax as a format for your file. This will require some study on your part, but again there are existing libraries to use, and it opens up the possibility of inter-operating more smoothly with other software, like S/MIME-enabled mail clients.
Password Validation
Regarding your desire to store a hash of the password, if you use PBKDF2 to generate the key, you could use a standard password hashing algorithm (big salt, a thousand rounds of hashing) for that, and get different values.
Alternatively, you could compute a MAC on the content. A hash collision on a password is more likely to be useful to an attacker; a hash collision on the content is likely to be worthless. But it would serve to let a legitimate recipient know that the wrong password was used for decryption.
Cryptographic Salt
Salt helps to thwart pre-computed dictionary attacks.
Suppose an attacker has a list of likely passwords. He can hash each and compare it to the hash of his victim's password, and see if it matches. If the list is large, this could take a long time. He doesn't want spend that much time on his next target, so he records the result in a "dictionary" where a hash points to its corresponding input. If the list of passwords is very, very long, he can use techniques like a Rainbow Table to save some space.
However, suppose his next target salted their password. Even if the attacker knows what the salt is, his precomputed table is worthless—the salt changes the hash resulting from each password. He has to re-hash all of the passwords in his list, affixing the target's salt to the input. Every different salt requires a different dictionary, and if enough salts are used, the attacker won't have room to store dictionaries for them all. Trading space to save time is no longer an option; the attacker must fall back to hashing each password in his list for each target he wants to attack.
So, it's not necessary to keep the salt secret. Ensuring that the attacker doesn't have a pre-computed dictionary corresponding to that particular salt is sufficient.
As Niyaz said, the approach sounds reasonable if you use a quality implementation of strong algorithms, like SHA-265 and AES for hashing and encryption. Additionally I would recommend using a Salt to reduce the possibility to create a dictionary of all password hashes.
Of course, reading Bruce Schneier's Applied Cryptography is never wrong either.
If you are using a strong hash algorithm (SHA-2) and a strong Encryption algorithm (AES), you will do fine with this approach.
Why not use a compression library that supports password-protected files? I've used a password-protected zip file containing XML content in the past :}
Is there really need to save the hashed password into the file. Can't you just use the password (or hashed password) with some salt and then encrypt the file with it. When decrypting just try to decrypt the file with the password + salt. If user gives wrong password the decrypted file isn't correct.
Only drawbacks I can think is if the user accidentally enters wrong password and the decryption is slow, he has to wait to try again. And of course if password is forgotten there's no way to decrypt the file.

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