How does Maven 3 password encryption work?

My answer is based on reading the Maven source code and doing a little research.

1. Does the encrypted master password provide security simply by existing in settings-security.xml in a folder that only one user can access (~/.m2)? If so, why bother with encrypting a 'master password' (why not just use some random value)? Isn't the 'master password' really just an entropy input to the cryptographic function? Calling it a password is confusing - I expected Maven to prompt me for this password before de-crypting any encrypted server passwords, but it did not.

The master password is an input into the cryptographic function for encrypting/decrypting the server passwords. If someone has your individual encrypted server passwords, they won't be able to decrypt them unless they also have your master password. This means you can freely share your maven settings.xml file with others, without them being able to decrypt your server passwords. This is also why the master password is kept in a separate file.

This rationale is somewhat explained in encryption guide

2. Do the master password and server passwords use the same encryption process/cipher? The server passwords are based on the master password, so there must be some difference in the algorithm. Where is the source code for this located?

From what I can tell, the master password is encrypted using the same cipher as the server passwords. When decrypting the server passwords, the master password (unencrypted form) is an input; when decrypting the master password, the magic string '"settings.security"' is used as the additional input.

You can see the source code PBECipher and MavenCli.java.

3. I have observed that the same master password or server password encrypted multiple times gives different hashes. According to Marcelo Morales' answer on How does maven --encrypt-master-password work, this is because 'a JVM-configuration-specific (usually SHA1PRNG) 64-bit random salt' is added to the password prior to encrypting. Maven decrypts stored passwords when they are used at compile time. Doesn't this mean the salts have to be stored somewhere?

A traditional approach to handling salts is that the random salt is stored with the encrypted text, alongside it. See the Wikipedia article.

Based on the source code linked above, the salt appears to be stored as the first 8 bytes of the Base64 decoded bytes, right before the encrypted password.

4. I have also observed that a regular password encrypted using one encrypted master password will still work if the master password is re-encrypted and stored in the settings-security.xml file, even though the encrypted master password ciphertext is now different. Can someone explain how this works?

This is because the decrypted form of the master password is used, not the encrypted "ciphertext". Thus re-encrypting it doesn't affect the server password encryption/decryption.

I don't know the answer to your last two (5 and 6) questions.

I need to know this for bnd(tools) so I can share some deeper analysis.

The 'encrypted' passwords have a syntax of:

output    ::= '{' base64(packet) '}'
packet    ::= salt[8] padlen[1] encrypted[?] padding[padlen]
salt      ::= <random>
padlen    ::= <length of padding >
padding   ::= <random to make packet length a multiple of 16>

The cipher used is AES/CBC/PKCS5Padding. The secret key and initialisation vector is calculated as follows:

sha = sha256( X + salt[8] )
key = sha[0..16]
iv  = sha[16..32]

For the master password X is "security.settings". Since this is a well known constant the master password is not encrypted but only obscured. For the server passwords X is the decoded master password.

Why the resulting packet is padded seems a waste of bytes since the packet format makes it trivial to strip and they are never part of the encryption/decryption. They just add a few random characters to the base64 string.

The only way this is useful is using the relocation facility. For example, if you mount the settings-security.xml on a private mount on the build server. You can then you can freely share the settings.xml file in public repos. However, this is also a sucky solution since you need to mount it the same mount point for all your users and CI build servers.

Be aware that any plugin can decode all your server passwords so never use real passwords for the servers. Nexus can create proxy passwords.