How do you save and retrieve a Key/IV pair securely? - vb.net

I'm using VB.Net's RijndaelManaged (RM) to encrypt files, using the RM.GenerateKey and RM.GenerateIV methods to generate the Key and IV and encrypting the file using the CryptoStream class. I'm planning on saving this Key and IV to a file and want to make sure I'm doing it the right way. I am combining the IV+Key, and encrypting that with my RSA Public key and writing it out to a file. Then, to decrypt I use the RSA Private key on this file to get the IV+Key, split them up and set RM.Key and RM.IV to these values and run the decryptor.
Is this the best method to accomplish this, or is there a preferred method for saving the IV & Key?

That's the general idea. The IV does not need to be kept secret, however. Only the "secret key" is secret.
You might consider using a standard like S/MIME (or its underlying Cryptographic Message Syntax) for your file format. I'm not sure if Bouncycastle has ported their S/MIME (or PGP) libraries to .NET, or if .NET has S/MIME support built-in, but there is likely to be a free library available for your platform. A widely used open source library like this has probably been tested and scrutinized more closely than you'll be able to do yourself, and they implement protocols designed by experts in cryptography so your don't have to wonder what pitfalls you've overlooked.
The model you've described is similar to S/MIME's "KeyTransRecipientInfo" method for key exchange. A symmetric key is generated to encrypt the data, then that key is encrypted with the public key of each intended recipient. The encrypted key and the IV (which is not encrypted in this standard) are bundled with information about the algorithms used in a CMS structure. The encrypted data can be included in the same bundle, or be in an separate file.
PGP has mode that is an essentially equivalent.

Related

PKCS#1 vs PKCS#8 vs PKCS#12 for RSA keys

What is the recommended RSA key format to use if you only started using it nowadays?
I know that PKCS#1 is a format dedicated to RSA keys but do I need to avoid using it because it's old?
recommended RSA key format to use will be
PKCS#1, PKCS#8 or PKCS#12 ?
TL;DR: Use PKCS#1 only within your own identified scheme, use "inner" PKCS#8 / SPKI if you want to identify a key in a scheme. Use encrypted PKCS#8 when storing private keys and no better method is available; use PKCS#12 if you want to accomplish the same thing and you are using PKIX / X.509. PKCS#12 can also be used as a trust store, usually using a separate file.
I'll cover this because it is more about choosing an encoding than the inner working of RSA and other algorithms. If that wasn't the case then it should be posted on Cryptography, after searching for an answer on that Q/A site, of course.
First, here are the standards that we are talked about. They have been initially been created by RSA Laboratories, but currently they are being maintained as RFC's:
PKCS #1: RSA Cryptography Specifications Version 2.2: these specify the RSA cryptosystem, as well as specifying how the public- and private keys can be encoded.
PKCS #8: Public-Key Cryptography Standards (PKCS) #8:
Private-Key Information Syntax Specification Version 1.2 : This documen specifies "inner" PKCS#8 which describes the private key type and contains the encoded private key and the "outer" PKCS#8 which creates a cryptographic wrapper that can be used to encrypt the private key using a symmetric algorithm such as 3DES or AES.
PKCS#12: PKCS #12: Personal Information Exchange Syntax v1.1 : Despite the broad wording of the title, this is "a transfer syntax for personal identity information, including private keys, certificates, miscellaneous secrets, and extensions", i.e. it is about "personal information" in the form of cryptographic objects.
Another important document (or really set) was initially created by ITU-T, formerly known as CCITT, an international treaty organization:
X.509 is the basic standard for (digital) certificates, which are a mechanism to infer trust for public keys and related (identity) information contained within certificates, and to allow revocation of those certificates.
There are number of other standards in the X.5nn and X.6nn series that support X.509, but people generally just say "X.509" to mean all of them together.
However, the X.509 standards are quite large and complex, and back when they were new cost money to obtain, so IETF (the Internet Engineering Task Force) created a series of RFCs that form a "profile" (effectively, a subset) of X.509 for Internet use, called PKIX (Public Key Infrastructure using X.509). The main one here is:
RFC5280 Internet X.509 Public Key Infrastructure Certificate and Certificate Revocation List (CRL) Profile: this is the main standard that describes certificates and revocation lists, which are used by e.g. TLS for server and sometimes client authentication, by CMS and S/MIME for signing and/or encrypting data and email, for RFC3161 timestamping, in "JOSE" (JSON-based cryptography), and more.
just as X.509 is supported by other X-series standards, RFC5280 is supported by a number of other, related RFCs. In particular the representation of public keys IN PKIX certs is defined in RFCs 3279, 4055, 4491, 5480, 5756, 8410, 8692, 9295 (at least, there may be more I've missed).
First note that these standards are not independent of each other. PKCS#12 depends on PKCS#8 to encode the private key and X.509/PKIX to encode the certificates within this "container format". PKCS#8 depends on PKCS#1 to encode the private key when it is an RSA key (pair), and X.509/PKIX similarly uses PKCS#1 for the public key. PKCS#8 originally used PKCS#5 (not listed above) for password-based encryption, but PKCS#12 defined additional password-based encryption schemes, and now both PKCS#8 within PKCS#12 and "standalone" PKCS#8 frequently use either the PBEs from PKCS#12 or the "PBES2" scheme from PKCS#5v2 (that v2 is critical; the PKCS#5v1 schemes are now broken and obsolete).
These structures can and often are stored in text rather than binary, in which case the specifications of PEM in RFC 1421 and the extensions for PKIX related structures in RFC 7468 should be consulted.
Which one to use?
Now comes the question which one to use. However, before we talk about storing private keys: private keys have been designed to remain private. That means that you should choose the most secure method of storing and using them (that still would help fulfill your use case). Quite often it is better to generate and store private keys within a secure container such as a hardware device (HSM, TPM) or a system provided certificate- or key store.
After that it depends on what you are trying to achieve.
PKCS#1
PKCS#1 describes a simple, near-minimal format for an RSA public or private key. So if you're handling raw private keys and need to store them on a medium, you need some way to encode the key. This is why the leading RSA specification contains a method of encoding them. So you'd use this standard when you'd work with RSA on a relatively low level, basically when you'd have to specify your own protocol (which you should do if you'd use RSA at such a low level, cryptographic protocols should deserve their own specific section in the documentation).
Notes:
The PKCS#1 format for the private key also contains the public exponent. That means that it is easy to extract the public key from the private key.
PKCS#1 is often also stored in textual format called PEM, where it has "RSA PUBLIC KEY" or "RSA PRIVATE KEY" in the header. As you can see, the PEM header contains the key type to be able to distinguish between key types and their respective encoding formats.
PKCS#8
The inner format within PKCS#8 would be used if you need a way to identify the private key while using the binary construction. Basically it is a sequence of the key type followed by the key value. The key type consists of an algorithm identifier, which is encoded as an OID plus optional parameters. The original, and for a long time only, OID for an RSA key is defined in the PKCS#1 specifications:
The object identifier rsaEncryption identifies RSA public and private
keys as defined in Appendices A.1.1 and A.1.2. The parameters field
has associated with this OID in a value of type AlgorithmIdentifier
SHALL have a value of type NULL.
rsaEncryption OBJECT IDENTIFIER ::= { pkcs-1 1 }
Which means that the key is specified using 1.2.840.113549.1.1.1. Note that this doesn't indicate the algorithm to be used for that key. OTOH PKCS#1 (now) defines different OIDs for OAEP and PSS and their related parameters in that same appendix, and RFC4055 directs the use of those OIDs and parameters in public keys in PKIX certificates -- and 4055 is standards track while 8017 is not. [DaveT note: I suspect the statement about always using rsaEncryption is a leftover from v1 when it meant that the key didn't specify a signature hash like sha1withRSA.]
There is of course another reason to choose PKCS#8 and that's if you want to use a standard, documented, and (potentially) strong encryption for your private key. (PKCS#8 specifies the encryption with a very general AlgorithmIdentifier syntax, so it is possible to use a weak encryption algorithm, or a low and inadequate iteration count; however most software won't do so by default.) There is no official encryption method for a PKCS#1 private key, although OpenSSL (formerly SSLeay) -- and a huge number of things that have been developed to be compatible with OpenSSL -- uses an ad-hoc, PEM-based, and quite poor method (specifically for PBKDF it uses OpenSSL's EVP_BytesToKey function with ONE iteration of MD5; see numerous Qs on the crypto and security Stacks about how bad this is).
As indicated, PKCS#8 encoded information can be put within PEM headers. For the "inner" PKCS#8 structure the header "PRIVATE KEY" is used. For the encrypted "outer" structure the header "ENCRYPTED PRIVATE KEY" is used. (Both of these are in RFC7468, cited above.)
SPKI
SPKI is an acronym for SubjectPublicKeyInfo. It is the main method within the X.509/PKIX specification to describe a public key. It is almost identical to the "inner" PKCS#8 structure in the sense that it simply consist of a sequence of an algorithm identifier with the value of the public key. Usually the same algorithm identifier is even used for both the public and the private key. As with PKCS#8, the sole purpose is to be able to identify the key type.
These keys can be encoded within PEM, and they then would use "PUBLIC KEY" in the header analogous to "inner" PCKS#8.
X.509/PKIX
X.509 (or its Internet form, PKIX) specifies the certificate format used for instance for TLS, but also for CMS (the cryptographic message syntax originally specified in and still sometimes called PKCS#7) as well as S/MIME (the standard for secure email based on CMS) and many other protocols such as XMLenc and XMLdigsig but also code signing etc. etc. X.509 certificates can be used to create a PKI, a public key infrastructure. Certificates are the main method of distributing and trusting public keys. When creating a key pair, the public key is quite often simply stored within a certificate that also contains information about the holder of the certificate which can be a human, a "role" or system such as server.
For RSA to work it is usually required to not just have the public key but to establish trust in the public key. Otherwise you'd not know who's public key you would be using to verify a signature, or who you are encrypting data for. For that reason most protocols that have multiple entities must have some way of establishing the identity of those entities. Although there are other ways of establishing trust, X.509 is the most common hierarchical method of establishing trust, relying on trust of Certification Authorities to indicate trust of underlying parties and their certificates.
X.509 certificates are often encoded to text as well, which is unfortunately not directly indicated by the file extension (so a .cer, .crt, .cert or whatever can contain a binary encoding or textual encoding. Multiple (trusted) certificates are sometimes present in a single file as well. Certificates are indicated using the X.509
PKCS#12
PKCS#12 is what cryptographers usually call a container format. It contains a description of storing various cryptographic elements and, of course, a way of establishing what is stored and how to retrieve the information. PKCS#12 is is commonly used in two ways:
to store private keys with their certificate chain, starting with the certificate that contains the public key, followed by the certificate used to sign the certificate.
to store a set of trusted (CA) certificates so that certificate chains can be verified & validated.
Usually PKCS#12 files are used if a more secure method of storing these items such as the aforementioned hardware devices or key stores are not present. They offer protection by allowing the information including private keys and certificates to be encrypted using symmetric cryptography.

Encrypt with Public Key and decrypt with Private Key using elliptic-curve cryptography

everybody.
Is it possible to perform public key encryption flow for elliptic-curve cryptography?
https://en.wikipedia.org/wiki/Public-key_cryptography
I need to implement the following scenario:
Alice generates a message.
Alice encrypts it with Bob's public key.
Alice sends a message to Bob (via an insecure channel).
Bob gets the message.
Bob can decrypt this message only with his private key.
I can't find a proper method inside the tweetnacl lib (https://github.com/dchest/tweetnacl-js). Could somebody can direct me in the right direction?
Thank you in advance.
You should be looking for an ECIES implementation. Here is a random JavaScript library that seems to support it.
Elliptic Curves do not support a encryption primitive like RSA does. There is EC ElGamal but is not worth it due to the small key sizes and the amount of overhead of ElGamal.
To use curves with encryption you need to use hybrid encryption. ECIES is hybrid encryption: offline ECDH key agreement together with symmetric encryption performed using the derived secret key.
Note that ECIES is not well standardized. You may have to choose your own key derivation function, stream cipher or block cipher and mode of operation. For the key derivation method you could choose HKDF where available. AES in GCM mode seems a sane choice today for the cipher (the 12 byte IV may be set to zero or to a value derived from the "shared secret" as well). Libraries that support ECIES will probably have their own idea on what ECIES should look like, but beware of compatibility issues...
Isn't the encryption method in the documentation that you linked to for tweetnacl-js?
https://github.com/dchest/tweetnacl-js#naclboxmessage-nonce-theirpublickey-mysecretkey
nacl.box(message, nonce, theirPublicKey, mySecretKey)
Encrypts and authenticates message using peer's public key, our secret key, and the given nonce, which must be unique for each distinct message for a key pair.
Returns an encrypted and authenticated message, which is nacl.box.overheadLength longer than the original message.
You would use the recipient's public key as the third argument to the above function. You would use your own private key as the fourth argument. The library takes care of message integrity by creating a signature of the encrypted message, signed by your private key.
I will suggest you go to an easy library that makes the work for you, I specially like the python ecdsa module (https://github.com/warner/python-ecdsa), is easy and not complicated. Also read about how EC works will help you in make your decision.

Asymmetric cryptography with reversed key roles

I'm trying to implement licensing system for a software to prevent piracy.
For this I need to read a license file within the application, and I need to make sure this file is written by the owner company.
Asymmetric cryptography has good potential for this aim, but in other way around!
Asymmetric cryptography algorithms, like RSA, give you a Public key and a Private key which are used as follow:
Private keys are used to decrypt.
Public keys are used to encrypt.
But I need them like this:
Private keys to be used to encrypt.
Public keys to be used to decrypt.
A simplistic idea would be to switch the role of public and private keys, but there are posts saying that in RSA public keys can be generated from private ones which make this idea impractical.
So here's my question: Is there any asymmetric cryptography with reversed key roles?
If speaking about RSA public/private key pair can be used in both cases you described. When you use private key to encrypt then public key decrypts and vice-versa.
As you said public key can be derived from private key but not the other way.
If you want to prove the origin of licensing file, use RSA in signature mode. In signature mode a hash is computed from the data you want to protect and then encrypted using private key. The result -the digital signature - is appended to the protected data.
Verification process starts by decrypting the signature which gives you the hash. Then compute hash value from the data. Computed and decrypted value shall be the same.
There are a lot of libraries providing comfortable way of signature creation and verification. You can choose depending on the platform you use for your application development.
http://en.wikipedia.org/wiki/Digital_signature

Save a SecKeyRef Asymmetric Key Pair to disk as a Certificate

I have created two SecKeyRef items via SecKeyGeneratePair, but now I would like to turn the public key into a x509 Digital Certificate – and/or both the public and private keys into a PKCS #12 (.p12) certificate – and save it to disk as a file. This way I can do whatever I need to with it, including sending the certificates to other services or computers.
I would prefer to not use the keychain, but even with that I am having some trouble finding good documentation on exactly how to create a certificate out of a pair of SecKeyRefs, and writing them out as a certificate file.
You want the Security Transforms Programming Guide. It covers most of what you need for this. Some parts (like SecItemExport) are not documented in the reference documentation, only in the public header files. But SecItemExport is the new 10.7 way to handle this stuff.

Can I store a PGP key ring in a csp parameters key container?

i have been using PGP. I need to safely store our PGP keyring for our application that will be processing some pgp files. Can I believe that the PGP is Asymmetric cryptography and i should be able to store the information for keyring in a key container?
PGP is a hybrid cryptographic system i.e it uses a mix of public/private asymmetric and standard symmetric encyption/decryption. It generates a unique session ID which it uses to encrypt the data it then encrypts the session ID with your public key. It then adds the asymetric encrypted session ID to the symmetric encrypted data to produce the final ciphertext
For decryption, the private key is used to decrypt the session ID and then standard symmetric decryption to retrieve the plain text.
PGP stores two sets of keyrings - public keyrings and private keyrings.
So if you shipped the private keyring with your app then anyone could use the private key to decrypt the pgp files.
Public/Private key security is not a magic bullet it still relies on the user keeping their private key or keyrings safe
Here's a good link on how PGP works in more depth
You should check and see if there is a OS-level keystore to use for that sort of thing. Rolling your own solution is error-prone. Besides, why re-invent the wheel if you don't have to?