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I'm the author of the functionality that you're asking about (good question!). Ubuntu's Encrypted Home Directory feature uses eCryptfs as the filesystem encryption technology. eCryptfs is a layered filesystem built directly into the Linux kernel. It mounts one directory on top of another. The top directory is really just a "virtual" mountpoint. ...

Free space and used space look exactly the same to someone who only sees one version of the ciphertext. First, the basic idea of a secure block cipher is that you learn nothing about the plaintext block simply by observing the ciphertext block. You may be able to learn something about the plaintext from the surrounding context, such as by collecting more ...

I think the thing you are looking for is "escrow" as in http://en.wikipedia.org/wiki/Key_escrow. Be aware though that the security of your system is reduced to the hardness for an attacker to find the master password which might be much easier than breaking the disk encryption scheme

eCryptfs information leakage can occur through various channels. The most serious and common leakage point has been the swap. As mentioned, Ubuntu now encrypts that, but I am told that hibernate is broken with that enabled. Other distros don't necessarily go out of their way to make sure swap is encrypted when eCryptfs is used. eCryptfs makes no special ...

A good solution would be to hold the master password encrypted by a N+P sharing scheme, where a certain amount of perhaps board members, or third parties, would need to come together to be able to reconstruct the master password. c++ cryptopp does secret sharing (http://en.wikipedia.org/wiki/Shamir%27s_Secret_Sharing) through ...

So I answered this on security SE, then quickly realised I'd totally misread the question and explained everything you already know. The question in my mind can be summarised succinctly by - does encrypting data on a per-file basis as opposed to a whole disk basis add any risk to the cryptographic security of the whole (negating for a moment the fact that ...