Long time reader Bob O. sent the following (unencrypted) question to me in response to my GnuPG + mutt + OSX + GMail article:
This is an excellent question, and I did gloss over it in my original post.
My mobile phone is not currently encrypted, though I have thought about enabling that feature. Even if my mobile phone were fully encrypted, I’m still pretty suspicious of both Android and iOS against covert attacks from government actors. The Snowden revelations indicate that NSA, GCHQ, and potentially others have found very subtle ways to compromise a mobile phone without physical access to the device.
I could keep my private keys on a device at my house, but I’d have no real way of knowing if any of those devices were physically attacked in my absence. I realize it’s unlikely that someone would break into my house for the sole purpose of accessing my GnuPG private key, but this seems like an easy precaution to take. The media on a Raspberry Pi is simply an SD card or external HDD, both of which would be easy to make copies of and then reconnect. Similarly, I don’t keep my private key on my server at DigitalOcean because I have no way of knowing if the virtual machine had been cloned.
(Even absent a specific effort to obtain my GnuPG private key, the physical loss of a device containing said private key should necessitate a revocation of my public key. There’s simply no good way to know if the private key was compromised or not.)
My work laptop is usually with me. It’s a unibody MacBook, so it’s not easy to access the hard drive directly (though I admit to ignorance as to whether there are easy ways to clone the hard drive without removing it). It also employs full disk encryption, so none of the data on the device is (easily) available to anyone who might gain access to it. OSX is not immune to malware, but it is fairly resistant to it, in general. If an actor were able to compromise my work laptop by way of specially crafted malware, there’s little I could do: I don’t think I’m quite paranoid enough to spot (or react to) a custom attack against me, whereas I am savvy enough to spot (most of) the general kinds of malware looking for easy marks.
So while I do think OSX may have some security advantages over my mobile phone, it’s more a matter of limiting the exposure of my private key to the minimum number of devices that makes practical sense.
I do use a complex password for my private key, but if someone has access to a copy of my private key then they can attack it all day long. They can run through every permutation of every possible password until they get access. It might be time consuming, and it might be expensive, but eventually the key will be cracked.
This password for my private key is not stored in my password manager, and to the best of my knowledge not written down anywhere. By using the GPG agent I can avoid repeated entry of my private key password. This reduces, but does not eliminate, the risk of keyloggers.
There are additional things I can (and may) do to further enhance my security. I do not currently have an expiration on my GnuPG key. I should set one, and take the time to extend that expiration as needed, as long as my key hasn’t been compromised. I should also generate a revocation certificate.
I don’t believe that I’m the target of government (or other) surveillance, so extreme paranoia is not driving most of my decision making. Nonetheless, I’m trying to take reasonable precautions to protect my private key from easy exploitation. I do have an offline backup of my private key stored securely, in case my work laptop suffers a catastrophic failure. Hopefully I’ll never need to use it.