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Implemented features and fixes not present in the official Sylpheed release

  • (fix) PGP signature not verified properly when the message has no newline at the end. https://sylpheed.sraoss.jp/redmine/issues/288

  • (feature) Make it possible to select "Show signature check result in a popup window" only for bad signatures.

  • (feature) Support for encrypting and storing encrypted passwords using a master password. Read bellow for more details!

Master password

The master password feature is developed by Simeon Simeonov (sgs) and is currently in an experimental state.

Motivation

Currently Sylpheed is storing passwords in plain-text. One can always refrain from storing passwords and let Sylpheed prompt for them, but the more accounts one has, the more annoying this becomes.

The goal is to have the passwords stored in a secure way and let Sylpheed only prompt for the master password.

Security goals

  • attacker (A) should not be able to derive the password from the digest.

  • A should not be able to derive the master password even if she has read and write access to the storage.

  • A should not be able to determine the length of the encrypted password even if she has read and write access to the storage.

  • A should not be able to craft an edited password without obtaining the master password.

  • A should not be able to compromise the master password or force Sylpheed to store decrypted passwords even if she has access to a running Sylpheed.

  • a warning / prompt should be given if a user accidentally types in a "wrong" master password before decryption is initiated.

Usage in Sylpheed

  • backup your Sylpheed profile (often $HOME/.sylpheed-2.0)!

  • start Sylpheed and open "Configuration" -> "Common preferences..."!

  • select the "Master password" tab, enable "Use master password" and apply the changes!

  • restart Sylpheed (exit and then start Sylpheed again)!

  • you will be asked to type and verify a new master password.

  • set your new passwords from the "Configuration" -> "Edit accounts..."!

  • select "Automatically unload master password after session initialization" for increased security and decreased convenience.

Note: Sylpheed will automatically convert existing stored passwords, but it will not touch your backups. You will have to remove all remnants of plain-text passwords manually.

Choice of cryptographic primitives

The primary concern when selecting cryptographic primitives was portability. The desire was to go for primitives that are both strong and available in all supported production distributions of OpenSSL and LibreSSL.

Cipher

When it comes to implementation, there are several advantages in using stream cipher or a block cipher that behaves like a stream cipher when used in a certain mode of operation. One is avoiding to deal with padding.

AES-256 operating in CFB was selected for these reasons. ChaCha20 should be considered as a replacement in the future.

Hash-function

Hash-functions are used for:

  • key derivation
  • plain-text digest

Those operations do not have to use the same hash-function. (See the "Encryption & decryption scheme" section for more details!)

Key-derivation: Since AES-256 uses a 256 bits key, we need a hash-function with at least the same digest size or bigger. Since the digest (which is the key itself) is considered confidential and is stored only in memory for only a limited amount of time, SHA-256 is considered sufficiently strong for that purpose.

Size + plain-text + padding digest: Since the digest is created of both the plain-text and the plain-text size, as well as being encrypted, SHA-256 is considered sufficiently strong. SHA-512 may increase security at the price of adding additional 32 bytes to the encrypted password digest.

Stronger hash-functions like SHA-3 or BLAKE2b can be considered as a replacement in the future.

Master password digest

In order to be able to decide whether the user typed a "wrong" master password, before attempting to decrypt, Sylpheed stores a digest of the master password in 'master_password_hash' in sylpheedrc. 100000 iterations of PBKDF2_HMAC with SHA-512 and 16 bytes salt is used. Note that this digest is useless as a key and even if a plain-text that produces the same digest is found, it will most probably be useless as a master-password.

Encryption & decryption scheme

Encryption

Input:

  • plain-text password to be encrypted (P)

  • plain-text master-password used for key derivation (M)

  • integer minimum password length (0 < L < 100)

Output:

  • an encrypted password digest (base64) (B)

Operation:

  • generate 16 bytes of random data to be used as a salt (S)

  • derive the key (K): K = SHA_256(S + M)

  • produce a 2 byte string (N) indicating the length of P

  • generate random padding and set N:

    • if the length of P < L, produce L - P bytes of random data (R), N = "%02d"
    • if the length of P >= L, N = "-1"

  • produce a hash digest (H): H = SHA_256(N + P + R (if the length of P < L))

  • encrypt (E): E = AES_256_CFB_ENCRYPT(H + N + P + R (if the length of P < L), K, IV=S)

  • B = mpes1:BASE64_ENCODE(S + E)

example: mpes1:vo7lsIpD7i6byBA6+vlUoF4OVDfEe+aYRRk4FRtfJ2gMY8M43Kj6WfdfgbViIOl83bI4XEc96okhPW5Mla813aAR1gbPjDg0xmCyIbWOiUv/dg==

Decryption

Input:

  • encrypted password digest (base64) (B)

  • plain-text master-password used for key derivation (M)

Output:

  • plain-text password (P)

Operation:

  • remove the prefix (mpes1:) and base64-decode the rest of the digest: B = BASE64_DECODE(B)

  • fetch the first 16 bytes for the salt: S = B[0 : 15]

  • derive the key (K): K = SHA_256(S + M)

  • decrypt the rest of B (D): D = AES_256_CFB_DECRYPT(B[16 :], K, IV=S)

  • extract the first 16 bytes for the hash digest (H): H = D[0 : 15]

  • in order to detect data-inconsistency, assert H == SHA_256(D[16 :])

  • extract the next 2 bytes for the length of P (N): N = D[16 : 17]

  • fetch the plain-text:

    • if N == "-1" the password is the remaining bytes of D: P = D[18 :]
    • if N != "-1", extract the next N-bytes from D: P = D[18 : (18 + N)]

Limitations

  • currently only the 'password' and 'smtp_password' keys in accountrc are encrypted. A mechanism that allows for any key and even folders to be encrypted should be considered in the future.

  • currently it is not possible to select alternative ciphers, hash-functions and modes of operation (without editing the source code).

  • currently it is not possible to change your master password without having to (re)set your passwords manually.