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I am in the process of creating a file/files containing all of my logins/password info for various accounts. In the event of my untimely demise this file would be sent to the appropriate party(s). What is the most appropriate and/or most secure way to encrypt this sort of file? I was looking into TrueCrypt or AxCrypt but I am somewhat new to encryption and I am not sure if these sorts of programs provide appropriate security for information this important.

So far I am leaning towards TrueCrypt - if I go this route does TrueCrypt allow me to create a password/hash that secures the file that could be printed and stored in a safe?

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You can encrypt a file with a PSK using a huge variety of software options. You could even put your docs in a .zip and password protect it. But TrueCrypt could probably work too. – KnightOfNi Feb 14 '14 at 2:49
you can use bitlocker... more securily, encode your harddisk, where you need to enter a passcode to decrypt your harddisk and boot the pc up. Thus, even when you lost your pc, or someone steals it, they wont be able to gain access to your files. – cengizUzun Feb 14 '14 at 8:55
@cengizUzun I like the idea, but I need to be able to quickly and automatically email this encrypted file in the case of my untimely death. – Josh Mountain Feb 14 '14 at 9:00
than you should never shut your pc down... and store it encrypted, send it in the encrypted file format using a secure transport protocol, encyrpt the message, encryt the file. – cengizUzun Feb 14 '14 at 9:39
up vote 4 down vote accepted

I would suggest to you trying KeePass. It is a password management utility that allows you to store username/passwords for several accounts.

As far as I am concerned, KeePass encrypts all your account credentials using a master password. This information is stored into a encrypted file. Then, you can send or share this secured file whenever you want.

I hope it fits to your needs. You may get more info

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Most usable answer here as truecrypt requieres constant log in, log out to prevent having a container being constantly open and manual gpg is cumbersome with the same dissadvantages as truecrypt – Samuel Feb 14 '14 at 14:38
@Samuel I'm only vaguely familiar with keepass. How is entering a master password into keepass any different from truecrypt and gpg? – Luc Feb 15 '14 at 1:41
Is there anything similar to KeePass that works natively on OSX? The two OSX ports I see listed on the KeePass site are unofficial, seemingly out of date, and have relatively bad reviews. – Josh Mountain Feb 15 '14 at 2:39
@Luc it isn't but it has plenty of features actually handling the passwords. When you copy pwds into clipboard, keepas keepass keeps it only for a short time and clears it after that. Then you can automatically lock your container after non usage which. In true crypt you can mount and dismount as you wish but the overhead is larger as I would not recommend having always your secure container with plaintext pwds mounted and ready. I regard that even worse than storing it in the firefox' password manager (with encryption!) – Samuel Feb 15 '14 at 8:25
@Samuel Okay I see, thanks for the reply :) – Luc Feb 15 '14 at 20:47

I would recommend to use gpg to encrypt a file. You can use it on the command line so that you are very flexible.

For example, to encrypt a file with AES with a 256 bit key you simply call gpg as follows:

gpg -c --cipher-algo AES256 file.txt

After entering a passphrase the encrypted data is written into the file file.txt.gpg

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