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Bitcoin Mining Rate and Waste

Recently, the Bitcoin mining rate surpassed 1 exahash per second, or 1 quintillion SHA-256 hashes per second.

Bitcoin mining graph showing gigahashes per second over time.

If we do some quick math, we can determine the following:

  • If SHA-1 collisions can be found in 2^65.3 hashes, that's one SHA-1 collision found every 45 seconds.
  • Every combination of bits can be flipped in an 84-bit keyspace every year.
  • If mining is done strictly with ASICs and each ASIC can produce 1 trillion hashes per second, that's 1,000,000 ASICs.
  • If each ASIC above consumes 650 Watts of power, that's 650 Megawatts of power consumed.
  • At 650,000 kWh per ASIC, that's 1.3 million pounds of CO2 released into the atmosphere every hour if using fossil fuels.
  • Current global rate is about 160 Bitcoins mined per hour.
  • At $0.15 USD per kWh, that's $609 spent on electricity per Bitcoin mined. Bitcoin is currently trading at $376/BTC.

That's "back of the envelope" calculations, with some big assumptions made about the mining operation (how it's powered, who is powering it, etc.).

Of course, not all mining is using fossil fuels, not all miners are using ASICs, not all ASICs can do 1 trillion hashes per second (some more, some less), not all ASICs are consuming that wattage per rate, and the cost of electricity was strictly a U.S. figure. Of course, if you're using a GPU, or worse, a CPU for your mining, then you expending more electricity per the rate than ASICs are. That may help balance out some of the miners who are using renewable energy, such as solar power for their mining. Many Chinese and Russian mining data centers certainly have less overhead costs on electricity. You get the point- we've made some big assumptions, to come to some very rough "ballpark" figures. I don't think we're too far off.

So, according to those numbers, unless using renewable energy, cheaper electricity, or Bitcoin trading goes north of $610 USB/BTC mining for Bitcoin is a net loss. This comes at the expense of 1.3 million pounds of CO2 released into the atmosphere every hour. I would argue that Bitcoin is the worst idea to come out of Computer Science in the history of mankind.

Using Your Monitors As A Cryptographically Secure Pseudorandom Number Generator

File this under the "I'm bored and have nothing better to do" category. While coming into work this morning, I was curious if I could use my monitors as a cryptographically secure pseudorandom number generator (CSPRNG). I don't know what use this would have, if any, as your GNU/Linux operating system already ships a CSPRNG with /dev/urandom. So, in reality, there is really no need to write a userspace CSPRNG. But what the hell, let's give it a try anywho.

The "cryptographically secure" piece of this will come from the SHA-512 function. Basically, the idea is this:

  • Take a screenshot of your monitors.
  • Take the SHA-512 of that screenshot.
  • Resize the screenshot to 10% it's original size.
  • Take the SHA-512 of that resized file.
  • Take the SHA-512 of your previous two SHA-512 digests.
  • Take the last n-bits of that final digest as your random number.

Most GNU/Linux systems come with ImageMagick pre-installed, as well as the "sha512sum(1)" function. So thankfully, we won't need to install any software. So, here's a simple shell script that can achieve our goals:

# Produces random numbers in the range of [0, 65535].
# Not licensed. Released to the public domain.

cd ~/Private # assuming you have an encrypted filesystem mounted here

TS1=$(date +%Y%m%d%H%M%S%N)
import -window root ${TS1}.png
sha512sum ${TS1}.png > /tmp/SHA512SUMS

TS2=$(date +%Y%m%d%H%M%S%N)
convert -scale 10% ${TS1}.png ${TS2}.png
sha512sum ${TS2}.png >> /tmp/SHA512SUMS

DIGEST=$(sha512sum /tmp/SHA512SUMS)
printf "%d\n" 0x$(printf "$DIGEST" | awk '{print substr($1, 125, 128)}')

shred ${TS1}.png ${TS2}.png
rm ${TS1}.png ${TS2}.png
shred /tmp/SHA512SUMS
rm /tmp/SHA512SUMS

Running it for 10 random numbers:

$ for i in {1..10}; do sh; done

A couple things to note:

  • This is slow, due to taking the screenshot, and resizing it.
  • The data on your monitors should be sufficiently random. Chats, social updates, etc. The security of this will depend entirely on the entropy of the initial screenshot.
  • You really should be saving your screenshots to an encrypted filesystem, such as eCryptfs.
  • We're using timestamps with nanosecond accuracy to provide some additional entropy for the final SHA-512 digest.
  • This is using the last 4 hexadecimal characters to be converted to decimal. In reality, it could be anything, including some convoluted dynamic search algorithm in the string.

It's worth noting that the entropy of the initial screenshot is critical, which is actually difficult to accurately measure. So, it may help to have a chat window or more open, with recent chat logs. Same could be said for social update "walls", with the most recent updates (Twitter, Facebook, Goodreads, etc.). Having a clock with seconds ticking in a status bar can also help (although not unpredictable, at least semi-unique). Tabs in browsers, running applications, etc. The more unpredictable your workspace in the screenshot, the better off you'll be. But, people in general suck at randomness, so I'm not advocating this as something you should rely on for a cryptographically secure random number generator.

If you wanted, you could add this to a terminal, giving you a sort of "disco rave" before taking the screenshot:

# Disco lights in your terminal
# No license. Released to the public domain

while true; do
    printf "\e[38;5;$(($(od -d -N 2 -A n /dev/urandom)%$(tput colors)))m•\e[0m"

Get that running first, then take your screenshot. But then, if you're reading data off of /dev/urandom, you might as well do that for your random numbers anyway...

Disable Pocket From Iceweasel

I'm not sure who I should be more disappointed in- Mozilla or Debian. Iceweasel 43 recently arrived in Debian unstable, and with it, Pocket. For those who are not familiar, Pocket is a 3rd party service that allows users to save sites they want to read or visit for later. Provided the extension is installed, this allows users to sync pages they want to read for later, across devices and platforms.

But here's the catch: it's a proprietary non-free service-as-a-software-substitue (SaSS).

Thankfully, you can disable it, and it really isn't that difficult. Open up about:config in a new tab, and type "pocket" into the search filter. From there, set "browser.pocket.api" and "" to "localhost", and set "browser.pocket.enabled" to "false", then restart your browser.

Screenshot showing about:config with the above settings in place.

It really bothers me that Mozilla has enabled this sort of integration into their browser. Not only Pocket, but other proprietary or privacy invasive plugins and extensions also, such as "sponsored tiles" (which is finally removed), "encrypted media extensions", and "Hello" (which I haven't figured out how to disable). These sorts of things should be separate extensions or plugins that the user can install at their whim. Shipping it by default takes away freedom and choice, and it's turning the browser into a proprietary non-free software application.

What ultimately bothers me about this, is that Mozilla already has bookmark synchronization support, and their sync server is Free Software, allowing you to roll your own. Pocket doesn't offer anything that Mozilla Sync doesn't. I already have a "TOREAD" bookmark folder, where I can put pages I want to read later. And it's synched across all of my devices.

Mozilla pushing the 3rd party proprietary Pocket, and Debian shipping it in Iceweasel (thankfully, a bug is submitted) is a great disservice to users and a threat to software freedom.

Hopefully, Pocket goes the way of sponsored tiles, and gets removed.

Encrypted Account Passwords with Vim and GnuPG

Screenshot of terminal showing hidden password with Vim syntax highlighting


I've been a long-time KeepassX user, and to be honest, I don't see that changing any time soon. I currently have my password database on an SSH-accessible server, of which I use kpcli as the main client for accessing the db. I use Keepass2Android with SFTP on my phone to get read-only access to the db, and I use sshfs mounts on my workstations with KeepassX for read-only GUI access. It works great, and allows me to securely access my password databases from any client, mobile or otherwise.

However, I recently stumbled on this post on how to use Vim with GnuPG to create an encrypted file of passwords: I've heard about a GnuPG plugin for Vim for years now, and know friends that use it. I've even recommended that others use it as a simplistic means of keeping an encrypted password database, instead of relying on 3rd-party tools. However, I've never really used it myself. Well, after reading that post, I decided to give it a try.

Defining a specification

Ultimately, everything in that post I'm carrying over here, with only a couple modifications. First, fields should end with a colon, which include the comments. Comments could just be just a single line, or multi-line, but it's still a field just as much as "user" or "pass". Further, there should be a little flexibility in the field keywords, such as "user" or "username". Additionally, because I exported my Keepass db to an XML file, then used a Python script to convert it into this syntax, I also carried over some additional fields. So, I've defined my database with the following possible fields:

  • comment|comments
  • expire|expires
  • pass|password
  • tag|tags
  • type
  • url
  • user|username

Notice that I did not define a "title" as would be the case in the Keepass XML. The entry itself is the title, so I find this redundant. Also, you'll noticed I defined an additional "type" field. While not explicitly defined in the Keepass XML, it is implicitly defined with icons for entries. This could be useful for defining "ssh" vs "mysql" vs "ldap" vs "http" authentications when doing searching in the file.

So, an invalid example on is:

Super Ecommerce{{{
    user:   foobar
    pass:   g0d
        birthday:   1/1/1911
        first car:  delorean

This is invalid due to the "Comments" field. Fixed would be:

Super Ecommerce{{{
    user:   foobar
    pass:   g0d
        birthday:   1/1/1911
        first car:  delorean

Another valid entry could be:

Example {{{
    username: aarontoponce
    password: toomanysecrets
    type: http
    tags: internet,social,2fa
    comments: {{{
        backup codes: vbrd83ezn2rjeyj, p89r4zdpjmyys2k, rdh6e7ubz8vh82g, er4ug6vp25xsgn5
        2fa-key: "3udw mkmm uszh cw2a 5agm 7c3p 5x32 tyqz"

Notice that I have not defined file comments, such as those found in configuration files or source code. There is a comment section per entry, so that seems to be the fitting place for any and all comments.

I really liked the post, and how thought out the whole thing was, including automatically closing the PGP file after an inactivity timeout, automatically folding entries to prevent shoulder surfing, and clearing the clipboard when Vim closes. However, one oversight that bothered me, was not concealing the actual password when the entry is expanded. Thankfully, Vim supports syntax highlighting. So, we just need to define a filetype for GnuPG encrypted accounts, and define syntax rules.

Vim syntax highlighting

EDITED TO ADD: I tried getting the Vim syntax working in this post, but WordPress is clobbering it. So, you'll need to get it from pastebin instead. Sorry.

To get this working, we need a syntax file. I don't know if one exists already for this syntax structure, but it isn't too difficult to define one. Let's look at what I've defined in this pastebin, then I'll go over it line-by-line.

The first four lines in the syntax file define are just comments. Next is just a simple if-statement checking if syntax highlighting is enabled. If so, use it. The first interesting line is the following:

let b:current_syntax = "gpgpass"

This defines our syntax. Whenever we load a file with syntax highlighting enabled, and we set the "filetype" to "gpgpass", this syntax will be applied.

syntax case ignore

This just allows us to have "comment" or "Comment" or "COMMENT" or any variations on the letter case, while still matching and proving a highlight for the match.

After that, we get into the meat of it. This "syntax match" section allows me to conceal the passwords on the terminal to prevent shoulder surfing, even when the entry is expanded. this is done with setting the background terminal color to "red" and the foreground text color also to "red". Thus, we have red text on a red background. The text is still yankable and copyable, even with the mouse cursor, it's just not visible on screen.

The actual concealment is done with the regular expression. An atom is created to match "pass:" or "password:" surrounded by whitespace as the first word on the line. However, I don't want to conceal the actual text "pass:", just the password itself. So, the regular expression "\@<=" says to ignore our atom in the match, and only match "\S\+" for concealing. The concealment is achieved with red foreground text on a red background with:

highlight gpgpassPasswords ctermbg=red ctermfg=red

The rest of the syntax matching in that pastebin is for identifying our fields, and highlighting them as a "Keyword" using regular expressions. All field names will be highlighted the same color based on your colorscheme, as they are all defined the same. Thus, aside from the hidden password, there is uniformity and elegance in the presentation of the syntax.

Using the syntax in Vim

This syntax file won't do us much good if it isn't installed and Vim isn't configured to use it. We could save it system-wide to "/usr/share/vim/vim74/syntax/gpgpass.vim", or just keep it in our home directory at "~/.vim/syntax/gpgpass.vim". Whatever works.

Now that the syntax file is installed, we need to call it when editing or viewing GnuPG password files. We can use the vimrc from, with one addition- we're going to add "set filetype=gpgpass" under the "SetGPGOptions()" function. Now, I understand that you may edit encrypted files that are not GnuPG password files. So, you're going to get syntax highlighting in those cases. Or, you could enable the modeline and set a modeline in the password file. The problem with the modeline, is its long history of vulnerabilities. Most distributions, including Debain, disable it, and for good reason too. So, I'd rather have it set here, and unset the "filetype" if it's bothering me.

Here's the relevant config:

if has("autocmd")
    " GnuPG Extensions "

    " Tell the GnuPG plugin to armor new files.
    let g:GPGPreferArmor=1

    " Tell the GnuPG plugin to sign new files.
    let g:GPGPreferSign=1

    augroup GnuPGExtra
    " Set extra file options.
	autocmd BufReadCmd,FileReadCmd *.\(gpg\|asc\|pgp\) call SetGPGOptions()
    " Automatically close unmodified files after inactivity.
	autocmd CursorHold *.\(gpg\|asc\|pgp\) quit
    augroup END

    function SetGPGOptions()
    " Set the filetype for syntax highlighting.
	set filetype=gpgpass
    " Set updatetime to 1 minute.
	set updatetime=60000
    " Fold at markers.
	set foldmethod=marker
    " Automatically close all folds.
	set foldclose=all
    " Only open folds with insert commands.
	set foldopen=insert
endif " has ("autocmd")


What I like about this setup is the portability and simplicity. I am in a terminal on a GNU/Linux box most of my waking hours. It makes sense to use tools that I already enjoy, without needing to rely on 3rd party tools. This also closes the gap of potential bugs with 3rd party password managers leaking my passwords. I'm not saying that Vim and GnuPG won't be vulnerable, of course, but I do place more trust in these tools than the Keepass ones, to be honest.

As of right now, however, I am still a Keepass user. But, I wanted to put this together, and try it out for size, and see how the shoe fits. As such, I've exported my KeepassX database, encrypted it with GnuPG, configured Vim, and I'm off to the races. I'll give this a go for a few months, and see how I like it. I know it's going to pose issues for mp on my phone, even with ConnectBot and SSH keys. But, maybe I don't need it on my phone anyway. Time will tell.

Oh, and I can still view the database as read-only and still enjoy the syntax highlighting benefits by using "view /path/to/passwords.gpg" instead of "vim /path/to/passwords.gpg".

Multiple Encryption

I hang out in ##crypto in Freenode, and every now and then, someone will ask about the security of multiple encryption, usually with the context that AES could be broken in the near future. When talking about multiple encryption, they are usually referring to cascade encryption which has the form of:

CT = Alg_B(Alg_A(M, key_A), key_B)

The discussion revolves around the differences between "Alg_A" and "Alg_B". Such as using AES for "Alg_A" and Camellia for "Alg_B". Also, the discussion will include whether or not "key_A" and "key_B" should be the same key, or different.

Cascade encryption is more efficient in storage space than some alternatives, such as this one suggested by Bruce Schneier:

CT = Alg_A(OTP, key_A) || Alg_B(XOR(M, OTP), key_B),  where OTP is a true one-time pad

I'm not going to go into the theoretical concerns with multiple encryption. However, I would like to cover some practical considerations:

  1. Multiple key security.
  2. Long-term storage.
  3. Complexity.
  4. Host security.

Multiple key security

It should come as no surprise that when dealing with multiple encryption, that you are going to be dealing with multiple keys, if you choose to keep "key_A" and "key_B" separate. Probably the most difficult aspect of encryption implementations, is keeping the secret key secret. For example, key exchanges between machines over the scary Internet has been notoriously difficult to get correct. Current best practice is implementing authenticated ephemeral elliptic-curve Diffie-Hellman (ECDHE) when communicating secret symmetric keys between machines. So, not only do you need to communicate one key, but multiple keys when encrypting and decrypting data.

If the multiple-encrypted data is to be stored on disk, then keys will need to be retrieved for later. How are these stored? This isn't an easy question to answer. If you store them in a password manager, they are likely just getting single-encrypted, probably with AES. So, the security of your ciphertext rests on the security of your stored keys, likely protected by the very algorithm you are trying to safe-guard.

Now, you could use the same key for every encryption layer. But, this poses a theoretical concern (which I promised I wouldn't cover- sorry). If the same key is used for every layer, then if an attacker can recover the key through cryptanalysis of the first encryption layer, then the attacker could possibly decrypt all remaining layers. Obviously, you don't want to use ciphers where the decryption process is exactly the same as the encryption process. Otherwise, the second encryption process on the ciphertext would decrypt the first encryption! While not probable, this last scenario could even occur with different algorithms, such as AES and Camellia. So, it seems at least at a cursory glance, that using the same key for all encryption layers probably is not a wise idea. So, we're back to key management, which is the bane of cryptographers everywhere.

Long-term storage

In my opinion, a larger problem is that of storage. It's one thing to get multiple encryption correct and safe on the wire, it's another to place value on long-term data storage. Think about it for a second- what is the longest you have kept data on the same drive? In personal scenarios, I have some friends that have had personal backups for up to five years. To me, this is impressive. It's likely more common that data switches drives every couple of years. RAID arrays die, hardware is replaced, higher drive capacity is demanded, or even bit rot creeps in, destroying data (such as on magnetic or optical mediums). When push comes to shove, the encrypted data is just going to move from drive-to-drive. But, ask yourself this next question- what is the oldest data you have in your possession right now?

Let's be realistic here for a second. I would be hard-pressed to find data I stored back in 2000, 15 years ago. I could find some photos in photo albums, on mugs, and on Christmas cards, but I'm not 100% confident I could get the digital original. Despite my best efforts, accidents happen, mistakes are made, and data is just lost. I don't think I'm alone here. I've even worked for companies, with large budgets, that had a hard time recovering data that is 10+ years old. For one, it's expensive to hold on to data indefinitely, but a great amount of data also becomes less and less valuable as time progresses. Yes, I still use my same email account from 2004- Google has done a great job of keeping all of my emails these past 11 years, and I would expect other data service providers to do the same. But, how many of you have kept an email address for 10+ years? Or even the data, for that matter? (This blog is actually 11 years old as well- kudos to me on keeping the data going this long).

My point is, hardware fails and is changed. Your personal value on data also changes, and accidents happen. So you're concerned about AES being broken in 20 years, or even sooner. Do you think by that time you'll still place value on that encrypted data? Do you think you'll even still have access to it, or can find it? And, if so, will it really be that difficult to decrypt the AES data, and encrypt it with the current best practice encryption algorithm?


This is probably the problem you should be concerned with the most. As a collective group, we as developers have a hard time getting single encryption correct, let alone multiple encryption. This deeply enters the theoretical realm, which I promised I wouldn't blog about. But, you do have a practical concern as well- order of operations and correct implementations.

First, order of operations. It's one thing to do "double encryption", where only two algorithms are chosen and used. If you can't recall if you used AES first or second, it's a 50/50 shot at getting the order correct (provided you know which key belongs to which algorithm, otherwise it's a one-in-four chance). Imagine however, using three encryption layers, and lining the keys up correctly. Imagine the complexity of four layers, or more. Ugh. Seems like you certainly don't want to go higher than two layers.

Second, look at implementations. AES is AES. It shouldn't matter what algorithm does the calculations. But, implementations like to put "magic bytes" at the beginning of ciphertexts (OpenSSL, OpenPGP, etc.). This data is only valuable for that implementation, and even worst, for a specific subset of versions. Just imagine encrypting a file with OpenSSL version 1.0 now, and needing to decrypt it in 10 years. Will OpenSSL version X be able to read those magic bytes, and correctly decrypt the file? Or will it error out, unable to decrypt the data because the data structure of the magic bytes changed in that 10 year time frame?

So, it seems best to encrypt it with some programming language library, where you can control exactly what data is stored. But, as everyone will tell you while frothing at the mouth, "don't roll your own crypto". Technically, you aren't if you "import aes" and use the "aes" module provided by that language correctly. It just remains to be seen if you implemented it correctly to thwart an attacker. Crypto is hard and full of sharp edges. It's very difficult to get things right, without getting cut. Regardless, while the "aes" module might be available in 10 years, what about the "camellia" module, or whatever algorithm you chose for the second layer? Is it still in development, or was it abandoned due to either being broken, or lack of development? Can you find that module, so you can decrypt your data?

Host Security

In a more practical real-world, everyday person scenario, how secure is the host that is doing the multiple encryption? Do others have physical access to the machine? Is it free of viruses, malware, and other badware? Does the system run an encrypted filesystem? Where and how are backups stored? Who has access to those backups? So many more questions can be asked that judge the quality of the security level of the host storing or processing the data.

Viruses and malware would probably be my number one concern if the data was so valuable, as to be multiple-encrypted. So, I would probably encrypt the plaintext on one machine, encrypt the ciphertext on a second machine, and store it on a third machine, preferably air-gapped. Thus, if a virus exists on one machine, hopefully it doesn't exist on another, and hopefully it doesn't attach itself to my encrypted data, and hopefully the badware didn't report my plaintext to a botnet pre-encryption.

Physical host security is hard. People have crappy passwords protecting their workstations. Physical access can get the attacker root regardless. Systems are infected with badware all the time, just by visiting websites! So there is hardly a guarantee that your data is safe, even though it was encrypted multiple times with different keys and algorithms.

A Couple Thoughts

It hardly seems worth the effort to encrypt your data multiple times with different algorithms and different keys, provided the overhead necessary in managing everything (hardware and software). Further, in reality, modern encryption algorithms aren't usually broken. For example, DES as an algorithm, isn't broken- it just requires a small key space. So, encrypting your data multiple times is solving a problem that for the most part, just doesn't exist.

That's not to say that AES will remain secure in 10, 20, or 40 years. I'm not that naive. But, as a user, you do have the ability to switch algorithms when AES does break. So, decrypt your AES ciphertext, and encrypt it with SevenFish (sorry Bruce- bad joke). Keep it encrypted with SevenFish until that breaks, and then decrypt it, and encrypt it with whatever the new modern cipher is at the time (if you still have the data, it's still valuable to you, and all implementations can still work with the ciphertext).


In my opinion, don't worry about multiple encryption. Generate a GnuPG key pair, encrypt your data once, and be done with it.

Getting Root On The Nexus 6 With Android 6

This probably the 40th millionth time, since owning this phone, that I've needed to root my device. Because I keep doing it over and over, while also referring to past commands and notes, it's high time I blogged the steps. If I can benefit myself from my own blog post, then chances are someone else can. So, with that said, here's what we're going to do:

  1. Grab the latest Nexus factory images from Google.
  2. Update the phone by flashing all the images (without wiping user data).
  3. Flash the recovery with the latest TWRP image.
  4. Get root on the device with Chainfire's "system-less root" SuperSU package.
  5. Enable USB tethering and the wireless hotspot functionality.

Before beginning, I should mention that if the title isn't immediately clear, this post is specific to the Motorola Nexus 6, which is the phone I currently own. It's probably generic enough, however, to be applied to a few Nexus devices. Minus getting the factory Nexus images from Google, this might even be generic enough for non-Nexus devices, but you're on your own there. Proceed at your own risk. With that said, it's fairly hard to brick an Android phone these days.

Also, you need to make sure you have an unlocked bootloader. Google ships with the bootloader locked by default. Unlocking it, will wipe your user partition, meaning you will lose any and all user data (images, videos, text messages, application data, etc.). I'm going to assume that you've already unlocked the bootloader, and are ready to proceed.


If you don't want to read the post, and know what you're doing, here's the short of it:

$ tar -xf shamu-mmb29k-factory-9a76896b.tgz
$ cd shamu-mmb29k
$ adb reboot bootloader
$ fastboot flash bootloader bootloader-shamu-moto-apq8084-71.15.img
$ fastboot reboot-bootloader
$ fastboot flash radio radio-shamu-d4.01-9625-05.32+fsg-9625-02.109.img
$ fastboot reboot-bootloader
$ fastboot update
$ fastboot flash recovery twrp-
$ fastboot reboot recovery
(reboot normally)
$ adb push /sdcard/
$ adb reboot recovery
(install /sdcard/ from TWRP)
(do not install TWRP root)
(reboot normally)
(install build.prop editor from Google Play)
(set "net.tethering.noprovisioning" to "true")

Otherwise ...

Getting the Google Nexus factory images

Navigate to and grab the version you are looking for. For example, I recently wanted to flash 6.0.1, so I grabbed the "MMB29K" image. Before flashing, I find it critical to verify the checksums. They are "27dde1258ccbcbdd3451d7751ab0259d" for MD5 and "9a76896bed0a0145dc71ff14c55f0a590b83525d" for SHA-1. So, after downloading, I pulled up a terminal, and verified them:

$ md5sum shamu-mmb29k-factory-9a76896b.tgz
27dde1258ccbcbdd3451d7751ab0259d  shamu-mmb29k-factory-9a76896b.tgz
$ sha1sum shamu-mmb29k-factory-9a76896b.tgz 
9a76896bed0a0145dc71ff14c55f0a590b83525d  shamu-mmb29k-factory-9a76896b.tgz

After examination, it's clear these checksums match, so I'm ready to flash.

Flashing the images

This step does not require root on your device. I'll need to connect my phone to my computer via USB, and verify that I can talk to it via adb(1). This means installing the Debian "android-tools-adb" and "android-tools-fastboot" packages if they're not already. After installed, I should be able to verify that I can talk to the phone:

$ sudo apt-get install android-tools-adb android-tools-fastboot
$ adb devices
List of devices attached 
[serial number]      device

If your device is visible, we are ready to rock-n-roll. First, extract the tarball, and enter the directory:

$ tar -xf shamu-mmb29k-factory-9a76896b.tgz
$ cd shamu-mmb29k
$ ls -lh
total 2.3G
-rw-r--r-- 1 atoponce atoponce  124 Jan  1  2009 android-info.txt
-rw-r--r-- 1 atoponce atoponce 8.1M Jan  1  2009 boot.img
-rw-r----- 1 atoponce atoponce  11M Nov 18 16:59 bootloader-shamu-moto-apq8084-71.15.img
-rw-r--r-- 1 atoponce atoponce 6.2M Jan  1  2009 cache.img
-rw-r----- 1 atoponce atoponce  985 Nov 18 16:59 flash-all.bat
-rwxr-x--x 1 atoponce atoponce  856 Nov 18 16:59*
-rwxr-x--x 1 atoponce atoponce  814 Nov 18 16:59*
-rw-r----- 1 atoponce atoponce 964M Nov 18 16:59
-rw-r----- 1 atoponce atoponce 113M Nov 18 16:59 radio-shamu-d4.01-9625-05.32+fsg-9625-02.109.img
-rw-r--r-- 1 atoponce atoponce 8.8M Jan  1  2009 recovery.img
-rw-r--r-- 1 atoponce atoponce 2.0G Jan  1  2009 system.img
-rw-r--r-- 1 atoponce atoponce 136M Jan  1  2009 userdata.img

Notice a couple of things- first, there are shell scripts "" and "" for Unix-like systems. Also, notice the "bootloader-shamu-moto-apq8084-71.15.img" & "radio-shamu-d4.01-9625-05.32+fsg-9625-02.109.img" raw images, as well as the "". These are the only files we're going to concern ourselves with when flashing the phone.

However, we want to be careful that we don't flash "userdata.img". This will format your user partition and all user data will be wiped (see above). What we're going to do, is basically the same execution as the "" shell script. However, we're going to make just one small modification. Further, we need our phone already booted into the bootloader. As such, here's what we're going to do:

$ adb reboot bootloader
$ fastboot flash bootloader bootloader-shamu-moto-apq8084-71.15.img
$ fastboot reboot-bootloader
$ fastboot flash radio radio-shamu-d4.01-9625-05.32+fsg-9625-02.109.img
$ fastboot reboot-bootloader
$ fastboot update

Notice that I removed -w from that last command (if you looked in the "" shell script). That option wipes user data, which would be necessary if we wanted to return the phone back to factory state. We don't- we're just upgrading. Also, I don't see the need for "sleep 5". Just wait for the phone to successfully reboot before running the next command.

At this point, the phone is successfully updated. If you were to reboot the phone, it would be perfectly operational as if you did an OTA update, or purchased it from the store. However, we want root, so we have a few more steps to accomplish.

Getting and flashing TWRP

This step also does not require root on your phone. I prefer TWRP for my recovery on Android. It's touch-based, which sets the UI apart from the other recoveries, and it's Free Software, unlike ClockworkMod. Both of these are big wins for me. Grab the latest image at I downloaded twrp- Unfortunately, I couldn't find any checksums to check to verify the download. So, I installed it anyway, knowing I could flash the stock "recovery.img" if something goes wrong. So far, things have been great, so I calculated the checksums for you:

$ md5sum twrp- 
f040c3a26f71dfce2f04339f62e162b8  twrp-
$ sha1sum twrp-
40017e584879fad2be4043c397067fe4d2d76c88  twrp-
$ sha256sum twrp-
ebe5af833e8b626e478b11feb99a566445d5686671dcbade17fe39c5ce8517c7  twrp-

If those checkout, you should be safe in flashing. Currently, the phone should already be booted into the bootloader. If not, make sure it is. Once in the bootloader, we can flash TWRP then reboot normally:

$ fastboot flash recovery twrp-

Now, it's critical that we don't normally reboot the phone. If we do, recovery will be overwritten, and we'll have to reflash. So, while your phone is still booted into the bootloader, reboot it into recovery. You can do this by pressing the volume up/down arrows, until rebooting into recovery is available, and pressing the power button. This should boot you into TWRP. Now that you're there, you can reboot the phone normally.

It is possible that while booting, your phone will notify you that the system cannot be verified. One of two things will happen: either the boot will pause, and not go further, or will boot without despite the warning. If you flashed these exact versions, my phone boots without the warning at all. However, don't panic if you see it. Remember, you have the factory images. Just reflash the recovery.img, and you will be just fine.

More info can be found at

Getting and flashing SuperSU (getting root)

At this point, the phone should be booted into its regular state. We are now ready to root the phone. This means getting the latest SuperSU package, and installing it through TWRP. However, I need to throw out another caution. We'll be installing a beta version of SuperSU to do something called "system-less root". This means that the package will only be modifying the bootloader image to get root, and will not be touching the system partition. This is both good, and bad. It's good in that we only need to reflash the bootloader to remove root. It's bad in that this is experimental software, and really not ready for production. Further, unlike TWRP, SuperSU is proprietary software, which sucks. It does make me a bit nervous, to be honest, to rely on non-free closed-source proprietary software, on such a critical piece of my life. Proceed at your own risk.

As of this writing, you'll need to get the SuperSU package from the XDA forums at;=3. I grabbed version "". There may be updates since this post was published.

Unfortunately, again, I did not see any published checksums. So, I've installed it, with the knowledge of how to reflash my bootloader should I encounter problems.

$ md5sum 
$ sha1sum 
$ sha256sum 

Provided these checksums match, we're good to go. We need to push the ZIP to our phone with the Android debugger, and reboot into the TWRP recovery:

$ adb push /sdcard/
$ adb reboot recovery

From the TWRP interface, tap "Install" and install the /sdcard/ package. When it finishes, tap "Reboot". TWRP will ask if you would like to install the root provided by the image. You do NOT want to install this root- you just flashed one.

The phone should boot normally.

Enable USB tethering and the wireless hotspot

This step requires root. Finally, we want to enable the hotspot and tethering. Google is bending to wireless carriers, forcing the user to prove that they are subscribing to a cellular service that allows them to use USB tethering or the wireless hotspot. Personally, I find this dirty, and unfortunate. Even worse, is the fact that cellular providers think they can get away by charging double for using your own data. Data is data; it shouldn't matter if it comes from your phone, or your laptop connected to your phone. If they want to charge for overages on caps, whatever. But charging double, just because you connected your phone via USB? Or setting up a hotspot in your grandma's house, because she doesn't have WiFi but you have cellular coverage? Please. This is clearly grandfathered from the days of feature phones, where you couldn't tether or hotspot. So, you purchased a USB dongle to enable the hotspot. Even then, it was dirty, but it's clear that this is a byproduct of days gone by.

To enable tethering and the hotspot, you just need to add one line to /system/build.prop config file. Unfortunately, /system/ is mounted read-only. So, you'll have to remount it as read-write and edit the file. However, every attempt I have made at modifying it has ended up with an empty file- IE: losing all its contents. So, rather than editing it manually, there is an app for that.

Install Add "net.tethering.noprovisioning" and set the property to "true", then reboot your phone. At that point, you should be able to USB tether and setup a wireless hotspot.


This wasn't for the faint of heart or for someone who doesn't care about gaining the necessary control over their Android phone that root would give them (setting up firewalls, ad blockers, tethering/hotspot, etc.). However, as mentioned earlier, it's getting fairly difficult to hard brick and Android phone these days. Even better, the steps are getting somewhat standardized. IE: flash factory images, flash custom recovery, install SuperSU, & optionally enable tethering/hotspot.

Your GnuPG Private Key

This post is inspired by a discussion in irc:// about Keybase and a blog post by Filippo Valsorda.

I was curious just exactly how my private key is encrypted. Turns out, gpg(1) can tell you directly:

$ gpg --output /tmp/secret-key.gpg --export-secret-keys 0x22EEE0488086060F
$ gpg --list-packets /tmp/secret-key.gpg
:secret key packet:
	version 4, algo 17, created 1095486266, expires 0
	skey[0]: [1024 bits]
	skey[1]: [160 bits]
	skey[2]: [1023 bits]
	skey[3]: [1023 bits]
	iter+salt S2K, algo: 3, SHA1 protection, hash: 2, salt: ad8d24911a490591
	protect count: 65536 (96)
	protect IV:  01 1e 07 58 4a b6 68 a0
	encrypted stuff follows
	keyid: 22EEE0488086060F

Notice the line "iter+salt S2K, algo: 3, SHA1 protection, hash: 2, salt: ad8d24911a490591". In there, you see "algo: 3" and "hash: 2". What do those identifiers reference? If you refer to RFC4880, you can learn what they are:

Symmetric Encryption Algorithms

  1. Plaintext or unencrypted data
  2. IDEA
  3. 3DES
  4. CAST5
  5. Blowfish
  6. Reserved
  7. Reserved
  8. AES-128
  9. AES-192
  10. AES-256
  11. Twofish

Cryptographic Hashing Algorithms

  1. MD5
  2. SHA-1
  3. RIPEMD-160
  4. Reserved
  5. Reserved
  6. Reserved
  7. Reserved
  8. SHA-256
  9. SHA-384
  10. SHA-512
  11. SHA-224

I emphasized the defaults, which are CAST5 and SHA-1. So, your key is encrypted with the SHA-1 of your passphrase, which is used as the key for CAST5 to encrypt your private key. Thus, the whole security of your encrypted private key rests on the entropy of your passphrase, provided that sane defaults are chosen for the encryption and hashing algorithms, which they are.

CAST5 has been well analyzed and it is not showing any practical or near practical weaknesses. It is a sane default to chose for a symmetric encryption algorithm. However, CAST5 uses 64-bit blocks for encrypting and decrypting data, which may have some theoretical weaknesses. AES uses 128-bit blocks, and thus has a larger security margin. Because AES-256 is available as a symmetric encryption algorithm, there really is no reason to not use it, aside from feeling more secure.

SHA-1 is showing near practical attacks on blind collisions, but for use with keying a block cipher from a passphrase, it's still exceptionally secure. What is needed to break SHA-1 in this regard, is a pre-image attack. A pre-image attack is where you have the hash, but you do not know the input that created it. This is not brute force. This is able to break the algorithm in such a way, that provided with any hash, you can reliably produce its input. SHA-1 has a wide security margin here, so there really is nothing practical to worry about. However, with SHA-512 available, there is also really no reason why not to use a SHA-2 algorithm. In fact, aside from the increase security margin, SHA-512 is designed to work well on 64-bit platforms, but struggle with 32-bit. So this gives us an increased security margin, albeit negligible, against using something like SHA-256.

So, how can we change these? Turns out to be quite simple. All you need to do is specify the secret key symmetric encryption algorithm and hashing algorithm, then change your password (retype it with the same password if you don't want to change it):

$ gpg --s2k-cipher-algo AES256 --s2k-digest-algo SHA512 --edit-key 0x22EEE0488086060F
Secret key is available.

pub  1024D/0x22EEE0488086060F  created: 2004-09-18  expires: never       usage: SCA 
                               trust: unknown       validity: unknown
sub  1792g/0x7345917EE7D41E4B  created: 2004-09-18  expires: never       usage: E   
sub  2048R/0xCE7911B7FC04088F  created: 2005-07-04  expires: never       usage: S   

gpg> passwd
gpg> save

Now if we export our key, and look at the OpenPGP packets, we should see the new updates:

$ gpg --output /tmp/secret-key.gpg --export-secret-keys 0x22EEE0488086060F
$ gpg --list-packets /tmp/secret-key.gpg
:secret key packet:
	version 4, algo 17, created 1095486266, expires 0
	skey[0]: [1024 bits]
	skey[1]: [160 bits]
	skey[2]: [1023 bits]
	skey[3]: [1023 bits]
	iter+salt S2K, algo: 9, SHA1 protection, hash: 10, salt: 9c3dbf2880791f2e
	protect count: 65536 (96)
	protect IV:  db f5 e8 1c 98 03 99 7c 77 33 4e cd d3 3c 1f 4f
	encrypted stuff follows
	keyid: 22EEE0488086060F

Now I have "algo: 9" which is "AES256" and "hash: 10" which is "SHA512" protecting my private key. I've gained a little bit extra security margin at the cost of retyping my passphrase. Not bad. Now, I'd like to pose you a question:

If I were to publish my encrypted GnuPG private key, think I'm crazy?

Let's look at this for a second. We know that the key is protected with AES-256. AES remains secure, after 15 years of intense scrutiny and analysis, and is showing no signs of wear. It's the most used symmetric encryption algorithm that protects HTTPS, SSH, VPN, OTR, Tor, and even your GnuPG encrypted emails. It protects social security numbers, credit card transactions, usernames and passwords, patient health records, hard drives, and on, and on, and on. AES is secure.

So, breaking the encrypted key will be at least as hard as breaking AES, which seems to be a long shot. So, you would be better off attacking my passphrase. Knowing that it was used as the key for AES, and that it is hashed with SHA-512, we can write a brute force algorithm to generate passphrases, hash them with SHA-512, and attempt at decrypting the AES key. After all, we have the salt and the IV right there in plaintext in the packets. Turns out, there are already projects for this.

This should be a breeze. Unless, of course, you have sufficient entropy behind your passphrase. What is sufficient entropy? Well, take some time searching "entropy" on my blog. You'll quickly learn that I recommend at least 80-bits. 100-bits would give you a paranoid security margin, even with the password being hashing with a fast hashing algorithm like SHA-512.

So, if the private key is encrypted with AES-256, and the passphrase has sufficient entropy to withstand a sophisticated attack, and it is hashed with SHA-512, then I should have no concern posting my encrypted key into the open, right?

Without further ado, here is my encrypted GnuPG private key:

Hash: SHA512

Version: GnuPG v1

Version: GnuPG v1


Now that this is posted, I should expect everyone to steal my GnuPG identity, parading around as me, forging signatures, correct? No, it's not happening. I trust the crypto. I trust the math. I trust the software.

Why? Why am I doing this? Well, a recent discussion popped up on IRC about Keybase. Some don't like the fact that they are encouraging you to upload your encrypted private key to the server. Some claim that it is "insecure". However, didn't we just logically and reasonably conclude that AES and SHA-2 are protecting my best interests? So, if it's insecure, then it can't be due to the crypto. It must be something else. Let's look at all the risk factors:

Keybase servers are compromised and you use the web interface
If the server is compromised, then the attackers can modify the code, providing malicious JavaScript to the browser, so when you successfully decrypt your private key, it can be sent and stored elsewhere under their control. There is nothing you can do here. You are screwed. This is a very valid concern.

Keybase servers are compromised and you use the command line interface
The attackers only have access to your encrypted private key. Provided you never use the web interface, all encryption and decryption as handled out-of-band. This means that regardless of the Keybase server compromise, the attackers will never actually get to forge signatures using your GnuPG private key.

Your local client is compromised
There is nothing I can do for you here. Keybase isn't to blame, and not even the gpg(1) client can protect you. You have bigger problems on your hands than the attackers gaining access to your unencrypted GnuPG private key.

I think a lot of GnuPG users are paranoid about their key getting leaked, because they are unsure of exactly how it is stored. Hopefully this post lays those fears to rest. If there are still concerns about the leak of encrypted private keys, then it's probably due to a fear of not fully understanding the strength of passwords and their entropy requirements. However, if you meet the necessary password entropy requirements, and your key is encrypted with CAST5/SHA-1 or AES-256/SHA-512, there is nothing wrong with keeping a backup of your GnuPG key on Github, AWS, Dropbox, or other "cloud" hosting solutions.

Trust the math. Trust the software.

By the way, if you do successfully recover my private key passphrase (and I know you won't), I would be interested in hearing from you. Send me a signed email with my private key, and I'll make it financially worth your while. 🙂

Now Using miniLock

I have been a long proponent of OpenPGP keys for a way to communicate securely. I have used my personal key for signing emails since ~ 2005. I have used my key at dozens and dozens of keysigning parties. I have used my key to store account passwords and credentials with vim(1), Python, and so many other tools. I have used my key to encrypt files to myself. And so much more. There is only one problem.

No one is using my key to send me encrypted data.

Sure, when attending keysigning parties, it's an encryption orgy. Attendees will sign keys, then send encrypted copies to recipients. And, of course, people will send encrypted emails before and after the party, for various reasons. But, when the party dies down, and people get back to their regular lives, and very few actually send encrypted data with OpenPGP keys. Realistically, it's rare. Let's be honest. Sure, there's the one-off, either as a corporation (XMission uses OpenPGP extensively internally for password storage) or individuals (sending encrypted tax forms to a spouse or accountant), but by large, it's rarely used.

I have a good idea of why, and it's nothing ground breaking- OpenPGP is hard. It's hard to create keys. It's hard to manage the keys. It's hard to grasp the necessary concepts of public keys, private keys, encryption, decryption, signatures, verification, the Web of Trust, user identities, key signing parties, revocation certificates, and so much more.

OpenPGP is just hard. Very hard.

Well, in an effort to encourage more people, such as my family and friends that would not use OpenPGP, to encrypt sensitive data, I've jumped on board with miniLock. What is miniLock? Currently, it's a Free Software browser application for the Google Chrome/Chromimum browser (not an extension). It uses ECC, bcrypt, BLAKE2, zxcvbn, and a number of other tools that you really don't need to worry about, unless you want to audit the project. All you need is an email and a password. The keys are deterministically generated based on that.

Think about this for a second. You don't need a public and private keyring to store your keys. You don't need to upload them to a key server. You don't need to attend keysigning parties, worry about the Web of Trust, or any of that other stuff that makes OpenPGP the nightmare it is.

All you need is an email and a password.

Unfortunately, this does have one big drawback- your email or password can't change, without changing your keys. However, the miniLock keys are cheap- IE: you can change them any time, or create as many as you want. You only need to distribute your miniLock ID. In fact, the miniLock ID is the entire public key. So, they don't even need to be long term. Generate a one-time session miniLock ID for some file that you need to send to your accountant during tax season, and call it good.

However, I prefer long-term keys, so as such, I created 3 IDs, one for each email account that I use. If you want to send me encrypted data, without the hassle of OpenPGP, feel free to use the correct miniLock ID for the paired email address.

Email miniLock ID mWdv6o7TxCEFq1uN6Q6xiWiBwMc7wzyzCfMa6tVoEPJ5S qU7DJqG7UzEWYT316wGQHTo2abUZQk6PG8B6fMwZVC9MN 22vDEVchYhUbGY9Wi6EdhsS47EUeLKQAVEVat56HK8Riry

Don't misunderstand me. If you have an OpenPGP key, and would prefer to use that instead, by all means do so. However, if you don't want to setup OpenPGP, and deal with the necessary overhead, I can now decrypt data with miniLock. Maybe that will a better alternative for you instead.

Do XKCD Passwords Work?

You'll always see comments on web forums, social sites, blog posts, and emails about "XKCD passwords". This is of course referring to the XKCD comic by Randall Munroe describing what he thinks is the best password generator:

What no one has bothered asking, is if this actually works.

Lorrie Faith Cranor, director of the Carnegie Mellon Usable Privacy and Security Laboratory at Carnegie Mellon University, a member of the Electronic Frontier Foundation Board of Directors, and Professor in the School of Computer Science and the Engineering and Public Policy Department at Carnegie Mellon University, did ask this question. In fact, she studied to the point, that she gave a TED talk on the subject. The transcript of her talk can be found here. Here are the relevant bits (emphasis mine):

Now another approach to better passwords, perhaps, is to use pass phrases instead of passwords. So this was an xkcd cartoon from a couple of years ago, and the cartoonist suggests that we should all use pass phrases, and if you look at the second row of this cartoon, you can see the cartoonist is suggesting that the pass phrase "correct horse battery staple" would be a very strong pass phrase and something really easy to remember. He says, in fact, you've already remembered it. And so we decided to do a research study to find out whether this was true or not. In fact, everybody who I talk to, who I mention I'm doing password research, they point out this cartoon. "Oh, have you seen it? That xkcd. Correct horse battery staple." So we did the research study to see what would actually happen.

So in our study, we used Mechanical Turk again, and we had the computer pick the random words in the pass phrase. Now the reason we did this is that humans are not very good at picking random words. If we asked a human to do it, they would pick things that were not very random. So we tried a few different conditions. In one condition, the computer picked from a dictionary of the very common words in the English language, and so you'd get pass phrases like "try there three come." And we looked at that, and we said, "Well, that doesn't really seem very memorable." So then we tried picking words that came from specific parts of speech, so how about noun-verb-adjective-noun. That comes up with something that's sort of sentence-like. So you can get a pass phrase like "plan builds sure power" or "end determines red drug." And these seemed a little bit more memorable, and maybe people would like those a little bit better. We wanted to compare them with passwords, and so we had the computer pick random passwords, and these were nice and short, but as you can see, they don't really look very memorable. And then we decided to try something called a pronounceable password. So here the computer picks random syllables and puts them together so you have something sort of pronounceable, like "tufritvi" and "vadasabi." That one kind of rolls off your tongue. So these were random passwords that were generated by our computer.

So what we found in this study was that, surprisingly, pass phrases were not actually all that good. People were not really better at remembering the pass phrases than these random passwords, and because the pass phrases are longer, they took longer to type and people made more errors while typing them in. So it's not really a clear win for pass phrases. Sorry, all of you xkcd fans. On the other hand, we did find that pronounceable passwords worked surprisingly well, and so we actually are doing some more research to see if we can make that approach work even better. So one of the problems with some of the studies that we've done is that because they're all done using Mechanical Turk, these are not people's real passwords. They're the passwords that they created or the computer created for them for our study. And we wanted to know whether people would actually behave the same way with their real passwords.

So, in her research, XKCD passwords really didn't work out that well. They are longer in length, so they take longer to type, which increases the chance for error, and people are no better at remembering on XKCD passphrase, than they are a short string of random characters.

To me, this is unsurprising. If you look at the history of my blogging on passwords, you'll find that I continually advocate true random events to build your passwords, maximizing entropy. In my last post, I even blogged two shell functions that you can use to build XKCD passwords, and "monkey passwords" (monkeys generating passwords by banging away at a keyboard). Both target 80-bits of entropy in the generation. Check out the lengths:

$ gen-monkey-pass 9
cxqwtw63taxdr3zn	uaq4tbt43japmm2q	mptwrxhhb486yfuv
-cb73b9-kgzhmww3	s45t3x6r9smw-7yr	hjkgzkha-qup4gh4
34c5rg4ksw-aprvk	uug-2vq7pfze6dnp	s4qx4eazbnrd2pqe

$ gen-xkcd-pass 9
sorestdanklyAlbanyluckyRamonaFowler   (sorest dankly Albany lucky Ramona Fowler)
towsscareslaudedrobinawardsrenal      (tows scares lauded robin awards renal)
thinkhazelsvealjuggedagingscareen     (think hazels veal jugged agings careen)
tarotpapawsNolanpacketAvonwiped       (tarot papaws Nolan packet Avon wiped)
surgesakimbohardercruelArjunablinds   (surges akimbo harder cruel Arjuna blinds)
amountlopsedgemeaslyCannoninseam      (amount lops edge measly Cannon inseam)
EssexIzmirwizesPattygroutszodiac      (Essex Izmir wizes Patty grouts zodiac)
hoursmailedslamsvowedallowspar        (hours mailed slams vowed allow spar)
AfghanNigelnutriadillmoldertrolly     (Afghan Nigel nutria dill molder trolly)

XKCD passwords average 32 characters to achieve 80-bits of entropy, compared to 16 characters that "monkey passwords" produce. And, according to the research done by Lorrie, people won't necessarily recall XKCD passwords any easier than "monkey passwords". So, if that's the case, then what's the point? Why bother? Why not just create "monkey passwords", and use a password manager?

Exactly. It's 2015. There are password managers for your browser, all versions of every desktop operating system, command-line based utilities for servers, and even apps for your smartphone. There are plenty of "cloud" synchronization services to make sure each instance is up-to-date. At this point, your passwords should:

  • Contain at least 80-bits of entropy.
  • Be truly random generated (no influence from you).
  • Be unique for each and every account.
  • Be protected with two-factor authentication, where available.
  • Be stored in a password manager, that is easily accessible.

You'll remember the ones you type in frequently, and you'll memorize them quickly. The others are stored for safe keeping, should you need to recall them.

Password Generation in the Shell

No doubt, some people use password generators- not many, but some. Unfortunately, this means relying on 3rd party utilities, where the source code may not always be available. Personally, I would rather be in full control of the entire generation stack. I know how to make sure plenty of entropy is available in the generation, and I know which sources of entropy to draw on to maximize the entropy estimate. As such, I don't use tools like pwgen(1), apg(1), or anything else. I rely strictly on /dev/urandom, grep(1), and other tools guaranteed to be on every BSD and GNU/Linux operating system.

As such, the script below has been successfully tested in various shells on Debian GNU/Linux, PC-BSD, FreeBSD, OpenBSD, NetBSD, and SmartOS. If you encounter a shell or operating system this script does not work in, please let me know. Thanks to all those who helped me test it and offered suggestions for improvement.

So, with that said, here they are:

# No copyright. Released under the public domain.
# You really should have shuf(1) or shuffle(1) installed. Crazy fast.
    if [ $(command -v shuf) ]; then
        shuf -n "$1"
    elif [ $(command -v shuffle) ]; then
        shuffle -f /dev/stdin -p "$1"
        awk 'BEGIN{
            "od -tu4 -N4 -A n /dev/urandom" | getline
        {print rand()"\t"$0}'
| sort -n | cut -f 2 | head -n "$1"
    [ $(printf "$1" | grep -E '[0-9]+') ] && NUM="$1" || NUM="1"
    until [ "$I" -eq "$NUM" ]; do
        LC_CTYPE=C strings /dev/urandom | \
            grep -o '[a-hjkmnp-z2-9-]' | head -n 16 | paste -s -d \\0 /dev/stdin
    done | column
    [ $(printf "$1" | grep -E '[0-9]+') ] && NUM="$1" || NUM="1"
    [ $(uname) = "SunOS" ] && FILE="/usr/dict/words" || FILE="/usr/share/dict/words"
    DICT=$(LC_CTYPE=C grep -E '^[a-zA-Z]{3,6}$' "$FILE")
    until [ "$I" -eq "$NUM" ]; do
        WORDS=$(printf "$DICT" | shuff 6 | paste -s -d ' ' /dev/stdin)
        XKCD=$(printf "$WORDS" | sed 's/ //g')
        printf "$XKCD ($WORDS)" | awk '{x=$1;$1="";printf "%-36s %s\n", x, $0}'
    done | column

Nothing fancy about them. The first function, "shuff" is really just a helper function for systems that might not have shuf(1) or shuffle(1) installed. It's used only in the "gen_xkcd_pass" function. The next function, "gen_monkey_pass" acts like monkeys banging on the typewriter. It reads /dev/urandom directly, reading the printable characters that come out of it, counting them to 16, and putting them in an orderly set of columns for output as seen below. The input is a total set of 32-characters, giving each character exactly 5-bits of entropy. So, at 16 characters, each password comes with exactly 80-bits of entropy. The character set was chosen to stay entirely lowercase plus digits, and remain unambiguous, so it's clear, and easy to type, even though it may still be hard to remember. The function can take a numerical argument, for generating exactly that many passwords:

$ gen_monkey_pass 24
awdq2zwwfcdgzqpm	t54zqxus77zsu6j6	-2h6dkp93bjdb496
thm9m9nusqxuewny	qmsv2vqw-4-q4b4d	ttbhpnh4n7nue5g8
ytt6asky765avkpr	grwhsfmyz872zwk3	mzq-5ytdv8zawhy6
zb46qgnt62k74xwf	uydrsh2axaz5-ymx	6knh32qj4yk885ea
vky55q2ubgaucdnh	5dhk9t97pfja9phj	rhn2qg734p83wnxs
-q2hb833c-54z-9j	t33shcc55e3kqcd6	q6fwn3396h4ygvq4
232hr73rkymerpyg	u2pq-3ytcpc79nb9	7hqqwqujz4mxa-en
jj9vdj3jtpjhwcp6	mqc97ktz-78tb2bp	q7-6jug86kqhjfxn

The last function, "gen_xkcd_pass" comes from the "correct horse battery staple" comic from XKCD. On every Unix system, there is a dictionary file installed at /usr/share/dict/words or /usr/dict/words. On Debian GNU/Linux, it contains 99,171 words (OpenBSD contains 234,979!). However, many of them have the apostrophe as a valid character. Taking out any punctuation and digits, we are left with just lowercase and uppercase characters for our words. Further, the total word space is limited to at least 3 characters in length and at most 6 characters in length. This leaves us with 19,198 words, or about 14.229-bits of entropy per word. This means generating at least 6 words to achieve an 80-bit entropy minimum. For clarity, the password is space-separated to the right in parens, to make it more clear what exactly the password is, as shown below. Even if all 6 words have 6 characters (the password is 36 characters in total), the formatted line will never be longer than 80 characters in width, making it fit perfectly in an 80x24 terminal. It also takes a numerical argument, for generating exactly that many passwords:

$ gen_xkcd_pass 8
flyersepticspantearruinedwoo         (flyer septic span tear ruined woo)
boasgiltCurrywaivegalsAndean         (boas gilt Curry waive gals Andean)
selectpugjoggedlargeArabicbrood      (select pug jogged large Arabic brood)
titshubbubAswancartharmedtaxi        (tits hubbub Aswan cart harmed taxi)
Reaganmodestslowleessamefoster       (Reagan modest slow lees same foster)
tussleFresnoJensentheirsNohhollow    (tussle Fresno Jensen theirs Noh hollow)
Laredoriffplunkbarredhikersrearm     (Laredo riff plunk barred hikers rearm)
demostiffnukesvarlethakegilt         (demo stiff nukes varlet hake gilt)

Of course, as you can see, some fairly obscure words pop out as a result, such as "filt" and "rearm". But then, you could think of it as expanding your vocabulary. If you install the "american-insane" dictionary, then you can get about 650,722 words in your total set, bringing your per-word entropy north of 16-bits. This would allow you to cut your number of generated words down to 5 instead of 6, to keep the 80-bits entropy minimum. But then, you also see far more obscure words than with the standard dictionary, and it will take a touch longer to randomize the file.

This script should be platform agnostic. If not, let me know what isn't exactly working in your shell or operating system, and why, and I'll try to address it.

Setting Up A Global VPN Proxy on Android with L2TP/IPSec PSK

In my last post in this short series, I want to discuss how to setup a transparent proxy on your Android phone using the builtin VPN for L2TP. As usual, the same precautions apply here. Don't be stupid with your data, just because you can hide it from your ISP.

In general, I'm skeptical of VPN service providers, which is partially why I'm writing this post. There isn't a VPN provider on this planet that will go to jail for you. And I don't buy into the hype that they aren't logging your traffic. Too often, VPN providers have been all too hasty to turn over user account information and logs, when Big Brother comes knocking. Instead, install strongSwan on your own L2TP VPN server, in a datacenter you trust to handle your traffic, and configure your Android to use that.

Unlike the previous posts, this one does not require root access. To start, you need to navigate to "Settings -> More -> VPN":

vpn-0 vpn-1

Tap the "+" sign to add a new VPN configuration. In this example, we'll configure it to connect to an L2TP/IPSec PSK VPN. As such, you'll need to fill out the server address (pixelated here), and the IPSec pre-shared key. Give the configuration a name, such as "My VPN", and tap "SAVE".

vpn-2 vpn-3 vpn-4

When tapping on the "My VPN" defined configuration, you will be asked to authenticate with your credentials. These can be from the operating system accounting database, LDAP, NIS, or IPSec specific. Provide your username and password, and tap "Save account information" if you want to save the credentials to disk on the phone. Then tap "CONNECT". At this point, you should see a little key in the status bar, confirming that you are indeed connected to the VPN server. If you want, you can create a "VPN" quick-access widget on your home screen, so you can get immediate access to your "My VPN" configuration with a single tap.

vpn-5 vpn-6 vpn-7

Setting Up A Global Tor Proxy on Android with Orbot

In my last post, I explained how to setup a Global SSH proxy on Android with ConnectBot and ProxyDroid. In this article, I'll do the same thing, but with Orbot. Also, as with the last article, the same precautions apply here. If you're on an untrusted or unknown network, using an encrypted proxy can be helpful. However, just because you're using Tor, doesn't mean you should trust its network blindly either. There are all sorts of practical attacks on Tor that have been reaching the press lately, and you would be wise to read them, and proceed with caution.

With that said, sometimes all you want to do is get around a content filter, such as viewing Reddit at church, or getting on Twitter while at work. Of course, there are necessary risks with those actions as well. Basically, don't be an idiot.

With that out of the way, this requires that you have root access on your phone, and that you have installed the Orbot Android app. Once the app is installed, we really only need to make one adjustment, and that is enabling two check boxes: "Transparent Proxying" and "Tor Everything":


As something you should keep in mind, you may also want to check "Use Bridges". Relay bridges are entry nodes that are not listed in the main Tor directory. As such, it is more difficult for ISPs to filter them. If you suspect that your ISP is blocking all known entry nodes, then using bridges can be helpful to get around the problem. But, using bridges may be unnecessary. Check if your Tor connection is getting filtered first. If so, enable the use of bridges, otherwise, you're just fine using Tor without them.

Also, Orbot has some interesting settings, such as specifically setting a whitelist of entry and exit nodes, and a black list of nodes to avoid. If you know someone is operating a Tor node, and you trust them, then I would recommend setting them as either an entry or exit, whichever is appropriate. The reason for this, is it is not impractical for a well-funded organization to have a large number of entry and exit nodes. If so, they can build traffic profiles on who is connecting to the entry node, and which site they are visiting from the exit. However, by specifying specific nodes for either entry or exit (or both), you eliminate this threat. Sadly enough, I could not get this working with Orbot.

One last setting that has caught my eye, is "Tor Tethering". If you use your phone as a wireless hotspot, or USB tethering, you can also transparently route all the traffic from those connected clients through the Tor proxy. I haven't tested this yet with the latest version, but with previous versions of Orbot, it didn't work.

Other settings are listed below, page after page.

orbot-1 orbot-3 orbot-4 orbot-5 orbot-6

When at the main page of the app, long-tap the power button in the center of the droid, to connect to the Tor network. When the arms of the droid are down, you are not connected. When the arms are yellow, and pointing to the sides of the phone, the app is trying to get a connecting to the Tor network. When the arms are green, pointing up, you are fully connected, and can start enjoying your proxy.

orbot-0 orbot-7 orbot-8

Notice that when you are connected, an onion icon is in the status bar at the top of the phone, showing as a permanent notification. If you have "Expanded Notifications" set, you can get IP address and country information in the notification. If you swipe the droid right or left, the droid will spin, and you will end up with a new "Tor Identity". Basically, you'll be connected to a new set of nodes.

orbot-9 orbot-10 orbot-11

Tapping the "CHECK BROWSER" button at the bottom left of the landing screen will use your default browser app to connect to and verify whether or not transparent proxying over Tor is working.

Setting Up A Global SSH Proxy on Android with ConnectBot and ProxyDroid

I'm one that takes precautions with my data when on unfamiliar or untrusted networks. While for the most part, I trust TLS to handle my data securely, I find that it doesn't take much effort to setup a transparent proxy on my Android handset, to route all packets through an encrypted proxy.

In this case, I happen to work for the greatest ISP in the world, and so I have an SSH server in the datacenter. I wholly trust the network from my SSH server to the border routers, so the more traffic I can send that direction, the better. I realize that may not be the case for all of you. However, if you have an externally available SSH server on a trusted network, this post may be of interest.

First, setting up this proxy requires having root. I'm not going to cover how to get root in this post. You can find it elsewhere. Next, you'll need to apps installed; namely ConnectBot and ProxyDroid. Both are Free Software apps. Also, you can do this with SSH Tunnel on its own, if you have Android 4.2.2 or older. Unfortunately, it doesn't work for 4.3 and newer. I have Android 5.1, and it isn't setting up the firewall rules correctly.

Once they are installed, you'll want to set them up. Here I walk through setting up ConnectBot.

  1. Pull up ConnectBot from your app drawer, and setup a new connection by typing in the username, host, and optionally port.
  2. When asked if you want to accept the server's public SSH key, verify the key, then tap "YES"
  3. Enter in your password to connect, and verify that you can successfully connect to the remote SSH server.
  4. Now, disconnect, sending you back to the app's landing screen.

connectbot-1 connectbot-2 connectbot-3

  1. At this point, long-tap the SSH profile you just created, and tap "Edit port forwards".
  2. Tap the menu in the upper-right hand corner of the profile, and tap "Add port forward".
  3. Give the forward a nickname, such as "ProxyDroid".
  4. Tap "Dynamic (SOCKS)" from the list under "Type".
  5. Provide any source port. It must be above 1024, and cannot be currently in use. I find "1984" apropos.
  6. Leave the "Destination" blank, and tap "CREATE PORT FORWARD".

connectbot-4 connectbot-5 connectbot-6 connectbot-7

You now have sucessfully created a SOCKS listening port on localhost:1984. Now, we need to create software firewall rules in the phone, to globally forward all packets through localhost on port 1984, creating our transparent proxy. As such, pull up ProxyDroid, and I'll walk you through setting that up:

  1. In ProxyDroid, set "" as the "Host".
  2. Match the port with what you set in ConnectBot's port forward ("1984" in our example).
  3. Set the "Proxy Type" to "SOCKS5"
  4. Scroll to the bottom of the app, and check the checkbox for "Global Proxy".
  5. OPTIONAL: Check the checkbox for "DNS Proxy".

That last step will tunnel DNS requests through the proxy also. Unfortunately, I have found it to be buggy, and unstable. So, leaving it unchecked, unfortunately, gives you a stable encrypted SSH proxy experience.


Now that both are configured, connect to your remote SSH server with ConnectBot that you have configured, then enable the proxy by tapping the slider next to "Proxy Switch". You should have a running global SSH proxy from your smartphone to the remote SSH server, where all packets are being sent. You can visit a site that returns your external IP address, such as, to verify that the source IP address of the HTTP request is the same IP address as your SSH server. If so, your packets are being tunneled through your SSH connection.


md5crypt() Explained

Recently, the Password Hashing Competition announced its winner, namely Argon2, as the future of password hashing. It's long since been agreed that using generic-purpose cryptographic hashing algorithms for passwords is not a best practice. This is due to their speed. Cryptographic hashing algorithms are designed to be lighting fast, while also maintaining large margins of security. However, Poul-Henning Kamp noticed in the early 1990s that the DES-based crypt() function was no longer providing the necessary margins of security for hashing passwords. He noticed how fast crypt() had become, and that greatly bothered him. Even worse, was the realization that FPGAs could make practical attacks against crypt() in practical time. As he was the FreeBSD release engineer, this meant putting something together that was intentionally slow, but also with safe security margins. He chose MD5 as the basis for his new "md5crypt password scrambler", as he called it.

Before delving into the algorithm, the first thing you'll notice is the strange number of steps and mixing that PHK does with his md5crypt() algorithm. When I was reading the algorithm, the first question that popped into my mind was: "Why not just do standard key-stretching with the password?" Something like this (pseudocode):

digest = md5(password + salt).digest()
rounds = 1000
while rounds > 0:
  digest = md5(password + salt + digest).digest()
  counter -= 1

This certainly seems to be the most straightforward approach, and the entirety of the security is based on the cryptographic security of MD5. If you were concerned about the output digest being recognizable, it might make sense to scramble it. You could scramble the remaining bytes in a deterministic fashion, which PHK actually ends up doing before saving to disk.

But then it hit me: PHK wanted his new algorithm to be intentionally slow, even if using MD5. This means adding additional steps to mixing the password, which requires more CPU, and thus, more time. If raw MD5 could process 1,000,000 hashes per second, then standard key-stretching of 1,000 iterations would bring it down to 1,000 hashes per second. However, if adding additional operations slows it down by 1/N-iterations, the the resulting throughput would be 1,000/N hashes per second. I can see it now- anything to slow down the process, without overburdening the server, is a gain. As such, the md5crypt() function was born.

Here is the algorithm, including what I think may be a bug:

  1. Set some constants:
    "pw" = user-supplied password.
    "pwlen" = length of "pw".
    "salt" = system-generated random salt, 8-characters, from [./0-9A-Za-z].
    "magic" = the string "$1$".
    "itoa64" = is our custom base64 string "./0123456789ABCDEFGHIJKLMNOPQRSTUVWXYZabcdefghijklmnopqrstuvwxyz"
  2. Initialize digest "a", and add the password, magic, and salt strings to it:
    da = MD5.init()
  3. Initialize digest "b", and add the password, salt, and password strings to it:
    db = MD5.init()
    final = db.digest()
  4. Update digest "a" by repeating digest "b", providing "pwlen" bytes:
    for(pwlen; pwlen > 0; pwlen -= 16):
      if(pwlen > 16):
  5. Clear virtual memory
    memset(final, 0, length(final))
  6. Update digest "a" by adding a character at a time from either digest "final" or from "pw" based on each bit from "pwlen":
    for(i = pwlen; i; i >>= 1):
      if i % 2 == 1:
    dc = da.digest()
  7. Iterate 1,000 times to prevent brute force password cracking from going to fast. Mix the MD5 digest while iterating:
    for(i=0; i<1000; i++)
      tmp = MD5.init()
      if i % 2 == 0:
      if i % 3 == 0:
      if i % 7 == 0:
      if i % 2 == 0:
      dc = tmp.digest()
  8. Convert 3 8-bit words of digest "c" into 4 6-bit words:
    final = ''
    for a, b, c in ((0, 6, 12), (1, 7, 13), (2, 8, 14), (3, 9, 15), (4, 10, 5)):
      v = ord(dc[a]) < < 16 | ord(dc[b]) << 8 | ord(dc[c])
      for i in range(4):
        final += itoa64[v & 0x3f]
        v >>= 6
    v = ord(dc[11])
    for i in range(2):
      final += itoa64[v & 0x3f]
      v >>= 6
  9. Clear virtual memory:
    memset(dc, 0, length(dc))

Notice that between steps 5 and 6, the virtual memory is cleared, leaving the digest "final" as NULLs. Yet, in step 6, the for-loop attempts to address the first byte of digest "final". It seems clear that PHK introduced a bug in this algorithm, that was never fixed. As such, every implementation must add a C NULL in step 6, instead of final[0]. Otherwise, you will end up with a different output than the original source code by PHK.

Anyway, that's the algorithm behind md5crypt(). Here's a simple Python implementation that creates valid md5crypt() hashes:

from hashlib import md5

# $ mkpasswd --method='md5' --salt='2Z4e3j5f' --rounds=1000 --stdin 'toomanysecrets'
# $1$2Z4e3j5f$sKZptx/P5xzhQZ821BRFX1

pw = "toomanysecrets"
salt = "2Z4e3j5f"

magic = "$1$"
pwlen = len(pw)
itoa64 = "./0123456789ABCDEFGHIJKLMNOPQRSTUVWXYZabcdefghijklmnopqrstuvwxyz"

# Start digest "a"
da = md5(pw + magic + salt)

# Create digest "b"
db = md5(pw + salt + pw).digest()

# Update digest "a" by repeating digest "b", providing "pwlen" bytes:
i = pwlen
while i > 0:
    da.update(db if i > 16 else db[:i])
    i -= 16

# Upate digest "a" by adding either a NULL or the first char from "pw"
i = pwlen
while i:
    da.update(chr(0) if i & 1 else pw[0])
    i >>= 1
dc = da.digest()

# iterate 1000 times to slow down brute force cracking
for i in xrange(1000):
    tmp = md5(pw if i & 1 else dc)
    if i % 3: tmp.update(salt)
    if i % 7: tmp.update(pw)
    tmp.update(dc if i & 1 else pw)
    dc = tmp.digest()

# convert 3 8-bit words to 4 6-bit words
final = ''
for x, y, z in ((0, 6, 12), (1, 7, 13), (2, 8, 14), (3, 9, 15), (4, 10, 5)):
    # wordpress bug: < <
    v = ord(dc[x]) << 16 | ord(dc[y]) << 8 | ord(dc[z])
    for i in range(4):
        final += itoa64[v & 0x3f]
        v >>= 6
v = ord(dc[11])
for i in range(2):
    final += itoa64[v & 0x3f]
    v >>= 6

# output the result
print "{0}${1}${2}".format(magic, salt, final)

Ulrich Drepper created a "sha256crypt()" as well as "sha512crypt()" function, which is very similar in design, and which I'll blog about later.

It's important to note, that while PHK may have announced md5crypt() as insecure, it's not for the reasons you think. Yes, MD5 is broken, horribly, horribly broken. However, these breaks only deal with the compression function and blind collision attacks. MD5 is not broken with preimage or second preimage collisions. In the case of a stored md5crypt() hash, it requires either a brute force search or a preimage attack to find the plaintext that produced the hash. MD5 is secure with preimage attacks. The reason md5crypt() has been deemed as "insecure", is because MD5 is fast, fast, fast. Instead, password hashing should be slow, slow, slow, and no amount of creativity with MD5 can adequately address its performance. As such, you should migrate to a password hashing solution designed specifically to slow attackers, such as bcrypt or scrypt, with appropriate parameters for security margins.

The Chaocipher With Playing Cards

As you know, I am a cryptography hobbyist. More specifically, I have an interest in pencil and paper ciphers, also referred to as "hand ciphers" or "field ciphers". Since Bruce Schneier released his Solitaire Cipher for Neal Stephenson's book "Cryptonomicon" (known in the book as "Pontifex"), I have had a real desire to learn hand ciphers with playing cards, that I'll refer to as "card ciphers".

Further, in 1918, John F. Byrne invented a mechanical encryption system that he called "Chaocipher". He released an autobiography titled "The Silent Years", of which he describes the system without the algorithm, and releases a series of exhibits of ciphertexts for cryptography experts to break.

Unfortunately, because he didn't release the algorithm I think, no one took his encryption system seriously, despite his best efforts to get the War Department to use it. It wasn't until 2010 that the widow of John F. Byrne's son released the Chaocipher papers, mechanics, and artifacts to the National Cryptologic Museum in Maryland, that we finally fully understood the algorithm.

In this post, I am going to describe the algorithm using playing cards, whereas John F. Byrne's original invention required two circular rotating disks. Another hindering aspect to Byrne's invention was the mechanical engineering required. At best, the device is clunky and awkward to use. However, using playing cards, I think you'll find the system much more elegant, easier to carry around, and has the advantage of not being incriminating that you are carrying a cryptographic device. Playing cards were certainly available in the early 1900s, so it's unfortunate that he didn't think of using playing cards as the primary mechanism for the cipher.


The Chaocipher uses the concept of lookup tables to encrypt or decrypt a message. This is done by maintaining two separate alphabets. When encrypting a message, a character is located in the plaintext alphabet, and it's location is noted. Then, the ciphertext character is identified by locating the character in the ciphertext alphabet at the same position. After the ciphertext character has been recorded, both the plaintext and ciphertext alphabets are permuted. We'll get into those details in a moment, but first, let's set aside some definitions.

Because John F. Byrne's original invention required two circular disks, there are two definitions that you should be aware of:

The top of the wheel or circle. In our case, this will be the top of the pile.

The bottom of the wheel or circle. In our case, this will be in the middle of the pile (the 14th of 26 cards).

All 52 cards in a standard poker deck.
Either the red playing cards (Diamonds and Hearts) dedicated to the ciphertext alphabet, or the black playing cards (Clubs and Spades) dedicated to the plaintext alphabet. Each pile is exactly 26 cards.

Left alphabet
The red pile of playing cards containing the ciphertext characters A-Z.
Right alphabet
The black pile of playing cards containing the plaintext characters A-Z.

We will be treating our two piles (the red and black piles) as circular. The piles will always be face-up on the table and in our hands. The top card in the face-up pile will be the 1st card while the bottom card will be the 26th card. Because the pile is circular in nature, this means that the top and bottom cards in the pile are "next" to each other in succession. This means further, then, that the 14th card in the pile is our nadir, while the top card, or the 1st card in the pile, is our zenith.

Now that we've set that aside, we need to create some definitions so we know exactly which playing card in every suit is assigned to which English alphabet character. I've assigned them as follows:

Hearts and Spades Clubs and Diamonds
A 2 3 4 5 6 7 8 9 10 J Q K A 2 3 4 5 6 7 8 9 10 J Q K

This means that the English character "X" would be the Jack of Clubs in the plaintext "black" pile ("right alphabet" in Chaocipher-speak), and the Jack of Diamonds in the ciphertext "red" pile ("left alphabet" in Chaocipher-speak). This also means that the 8 of Spades would be the English character "H", just as much as the 8 of Hearts.

On a side note, if you wish to program this in software, and you populate an array with the values of 1 through 52 to represent each card in the deck, it's standard to use 1-13 for the Clubs, 14-26 for the Diamonds, 27-39 for the Hearts, and 40-52 for the Spades ("bridge order").


The algorithm can comprise of a standard "simple" set of steps, or using a more advanced "takeoff pattern" for enciphering and deciphering the message. First, let me discuss the simple pattern, then I'll look at the more advanced takeoff pattern.

An overview of the algorithm could be described as follows:

  1. Determine the ciphertext character according to the plaintext character (and vice versa for decryption).
  2. Permute the red pile.
  3. Permute the black pile.

Each of these three steps are executed in order until the message is exhausted.

Enciphering Plaintext

Looking at it in closer detail, suppose I had the following red and black piles (using "+" to identify the zenith, and "*" to identify the nadir):

            +                                      *
  red (ct): 7D 3H TH 2H JD AD 8H 8D 5H TD QH 9H JH 2D 6D KH QD 9D 5D KD AH 7H 6H 4H 4D 3D
black (pt): TC 3S JS 2C 5S AC 4C KC 9S TS 9C 6S 7S 8S QS QC 7C JC 4S 3C 8C AS 2S 5C KS 6C

If I wanted to encrypt the character "A", in the black deck, according to our table above, that would be the Ace of Spades. As such, I need to find the Ace of Spades in my black pile. While locating the card, I need to be counting, so I know the position in the pile that the Ace of Spades in in. In this case, the Ace of Spades is the 22nd card in the black pile. Thus, the 22nd card in the red pile is the Seven of Hearts:

            +                                      *                       ↓
  red (ct): 7D 3H TH 2H JD AD 8H 8D 5H TD QH 9H JH 2D 6D KH QD 9D 5D KD AH 7H 6H 4H 4D 3D
black (pt): TC 3S JS 2C 5S AC 4C KC 9S TS 9C 6S 7S 8S QS QC 7C JC 4S 3C 8C AS 2S 5C KS 6C

The Seven of Hearts produces the English character "G". Thus, with these two piles, "A" encrypts to "G" before permutation. Conversely, "G" would decrypt to "A" with these starting piles.

Permuting the Red and Black Piles

Now that we've discovered our plaintext and ciphertext characters, we need to cut the deck, such that both the plaintext and ciphertext characters are at the zenith of each pile. The resulting piles would then be as follows:

            +                                      *
  red (ct): 7H 6H 4H 4D 3D 7D 3H TH 2H JD AD 8H 8D 5H TD QH 9H JH 2D 6D KH QD 9D 5D KD AH
black (pt): AS 2S 5C KS 6C TC 3S JS 2C 5S AC 4C KC 9S TS 9C 6S 7S 8S QS QC 7C JC 4S 3C 8C

Permuting the Red Pile

Permuting the red pile follows the following steps:

  1. Remove the zenith + 1 card (2nd card) from the red pile.
  2. Place the removed card into the nadir of the red pile (will be the 14th card).

So, we'll follow these steps by taking the zenith + 1 card (2nd card), which is the "6H", and placing it at the nadir of the red pile (14th card). The resulting red pile will look as follows:

            +                                      *
  red (ct): 7H .. 4H 4D 3D 7D 3H TH 2H JD AD 8H 8D 5H TD QH 9H JH 2D 6D KH QD 9D 5D KD AH

            +                                      *
  red (ct): 7H 4H 4D 3D 7D 3H TH 2H JD AD 8H 8D 5H .. TD QH 9H JH 2D 6D KH QD 9D 5D KD AH

            +                                      *
  red (ct): 7H 4H 4D 3D 7D 3H TH 2H JD AD 8H 8D 5H 6H TD QH 9H JH 2D 6D KH QD 9D 5D KD AH

Permuting the Black Pile

Permuting the black pile follows the following steps:

  1. Take the zenith (top) card and place it at the bottom of the black pile.
  2. Remove the zenith + 2 card (3rd card) from the black pile.
  3. Place the removed card into the nadir of the black pile (will be the 14th card).

So, we'll follow these steps by taking the zenith card (top card), which is the "AS", and placing it at the bottom of the black pile. The resulting black pile will look as follows:

            +                                      *
black (pt): 2S 5C KS 6C TC 3S JS 2C 5S AC 4C KC 9S TS 9C 6S 7S 8S QS QC 7C JC 4S 3C 8C AS

Now take the zenith + 2 (3rd card), which is the "KS" and place it at the nadir of the black pile (14th card). The final black pile will look as follows:

            +                                      *
black (pt): 2S 5C .. 6C TC 3S JS 2C 5S AC 4C KC 9S TS 9C 6S 7S 8S QS QC 7C JC 4S 3C 8C AS

            +                                      *
black (pt): 2S 5C 6C TC 3S JS 2C 5S AC 4C KC 9S TS .. 9C 6S 7S 8S QS QC 7C JC 4S 3C 8C AS

            +                                      *
black (pt): 2S 5C 6C TC 3S JS 2C 5S AC 4C KC 9S TS KS 9C 6S 7S 8S QS QC 7C JC 4S 3C 8C AS

As such, both the red and black piles should look like the following after enciphering the plaintext character "A" and permuting both piles:

            +                                      *
  red (ct): 7H 4H 4D 3D 7D 3H TH 2H JD AD 8H 8D 5H 6H TD QH 9H JH 2D 6D KH QD 9D 5D KD AH
black (pt): 2S 5C 6C TC 3S JS 2C 5S AC 4C KC 9S TS KS 9C 6S 7S 8S QS QC 7C JC 4S 3C 8C AS

To summarize, the algorithm steps are as follows:

  1. Find the plaintext character in the black pile.
  2. Record the position of this card in the black pile.
  3. Find the ciphertext character in the red pile by counting to that position.
  4. Bring the plaintext character to the zenith by cutting the deck at that position.
  5. Bring the ciphertext character to the zenith by cutting the deck at that position.
  6. Permute the red pile:
    1. Remove the zenith + 1 card from the red pile (2nd card).
    2. Insert the removed card into the nadir of the red pile (14th location).
  7. Permute the black pile:
    1. Move the card at the zenith to the bottom of the black pile.
    2. Remove the zenith + 2 card from the black pile (3rd card).
    3. Insert the removed card into the nadir of the black pile (14th location).

Make sure you understand these steps before continuing.

Permuting with a Takeoff Pattern

John F. Byrne described a "takeoff pattern" in which the left and right alphabets are used for both the plaintext and ciphertext characters. In the simple method, the right alphabet (black pile) is used exclusively for all plaintext characters in the message. So, if the plaintext message was "ATTACKATDAWN", then you could think of using the right pile 12 times, or "RRRRRRRRRRRR" ("BBBBBBBBBBBB" if we're thinking "black pile").

However, suppose you would like to use both of the red and black piles (left and right alphabets respectively) for your plaintext message. Then you could create a "takeoff pattern" for encrypting your text. Suppose you used the following takeoff pattern: "RLRRLLRRRLLL" (right, left, right, right, left, left, right, right, right, left, left, left). This means that you would use the right alphabet for the first plaintext character, then the left alphabet for the second plaintext character, the right alphabet for the 3rd, the right alphabet for the 4th, etc. Or, if using playing cards, you could think of the same takeoff pattern as "BRBBRRBBBRRR" (black, red, black, black, red, red, black, black, black, red, red, red).

Personally, I don't care for the takeoff pattern for two main reasons: first, the takeoff pattern needs to be communicated with the key. This may not be a problem if code books are distributed among field agents, as the takeoff pattern can be printed on the same page as the key. However, this does mean that the takeoff pattern needs to be as long as the key itself.

The second reason I don't care for the take of pattern, is due to the unnecessary complexity of the takeoff pattern itself, it greatly increases the chances to make a mistake. Already, the sender and recipient will be going back and forth frequently between the red and black pile of cards. By creating a takeoff pattern, this makes that back and forth more frequent. Further, if you are using the 3rd of 5 "L"s in a stream, but you think you are on the 4th "L", then the encryption or decryption will be wrong from there out. Chaocipher doesn't have the ability to correct itself from a mistake.

For these two reasons, I suggest that when using playing cards with the Chaocipher, that instead you always use the black pile for the plaintext characters, and the red pile for the ciphertext characters. Then, the only thing that you need to keep track of is the characters in the message itself.

Keying the Deck

Before executing the Chaocipher algorithm, the deck should be "keyed". This refers to the order of the deck. Both the sender and the recipient must have the same deck order in order to successfully encrypt and decrypt a message. The deck can be keyed by either a sufficient set of shuffling and cutting, or keyed with a key phrase. First, let's look at thoroughly shuffling and cutting a full 52-card deck.

Keying with Shuffling and Cutting

Suppose after thoroughly shuffling and cutting the deck, the deck order face-up is as follows:

|< - top                                                                                                                                         bottom ->|
3H 8D QH 4C 6S QS 8C 4D 9S 5D 8S QC 3C 6H JS 7H 5S TS QD 7C 4H JC KD TH 3S KS 6D 9C 9D 2C JD 2H 2D 6C 8H KC 9H JH 7S KH AS AH 5C AD TC 7D 4S 3D 2S TD 5H AC

We now need a deterministic algorithm for separating the red cards from the black cards. Holding the deck face-up in your hand, deal out two face-down piles, the left pile of red cards, and the right pile of black cards. Do this card-for-card, one-at-a-time. Do not grab a bunch of similarly-colored cards. This can introduce error into the keying process. Doing it one-at-a-time ensures exactness, and minimizes the chances for mistake.

After the full deck has been dealt into two face-down piles, turn the piles over, so they are face-up. Using the standard Chaocipher tokens of "+" to identify the zenith, or top of the pile, and the "*" to identify the nadir, or 14th card in the pile, your two piles should be in the following order:

            +                                      *
  red (ct): 3H 8D QH 4D 5D 6H 7H QD 4H KD TH 6D 9D JD 2H 2D 8H 9H JH KH AH AD 7D 3D TD 5H
black (pt): 4C 6S QS 8C 9S 8S QC 3C JS 5S TS 7C JC 3S KS 9C 2C 6C KC 7S AS 5C TC 4S 2S AC
  position:  1  2  3  4  5  6  7  8  9  1  1  1  1  1  1  1  1  1  1  2  2  2  2  2  2  2
                                        0  1  2  3  4  5  6  7  8  9  0  1  2  3  4  5  6

Verify that you can do this by hand, and that it matches with the deck order above. Remember, the red pile is our "left alphabet" in the Chaocipher which contains all ciphertext English characters. The black pile is our "right alphabet" in the Chaocipher which contains all plaintext English characters. In other words, if we converted them to English characters, then the left and right alphabets would be as follows, using the same notation to identify the zenith and nadir:

            +                         *
 left (ct): C U L Q R F G Y D Z J S V X B O H I K M A N T P W E
right (pt): Q F L U I H Y P K E J T X C M V O S Z G A R W D B N
  position: 1 2 3 4 5 6 7 8 9 1 1 1 1 1 1 1 1 1 1 2 2 2 2 2 2 2
                              0 1 2 3 4 5 6 7 8 9 0 1 2 3 4 5 6

Keying with a Key Phrase

Already knowing the algorithm prepares you for using a key phrase to key the deck. Basically, you'll just use the characters in your key phrase as the plaintext message, using the black pile to find key key phrase character, just as you would if encrypting a message. Both piles will be permuted, as normal. The only difference is that you will be not be recording the ciphertext characters. Further, you will start with alphabetized piles.

Both piles will start with the following order:

            +                                      *
 left (ct): AH 2H 3H 4H 5H 6H 7H 8H 9H TH JH QH KH AD 2D 3D 4D 5D 6D 7D 8D 9D TD JD QD KD
right (pt): AS 2S 3S 4S 5S 6S 7S 8S 9S TS JS QS KS AC 2C 3C 4C 5C 6C 7C 8C 9C TC JC QC KC

Suppose our key phrase is "CHAOCIPHER". Then, working through the steps character for character, they would follow the following order:

Locate "C" in the black pile:
            +                                      *
 left (ct): AH 2H 3H 4H 5H 6H 7H 8H 9H TH JH QH KH AD 2D 3D 4D 5D 6D 7D 8D 9D TD JD QD KD
right (pt): AS 2S 3S 4S 5S 6S 7S 8S 9S TS JS QS KS AC 2C 3C 4C 5C 6C 7C 8C 9C TC JC QC KC

Bring both characters to zenith:
            +                                      *
 left (ct): 3H 4H 5H 6H 7H 8H 9H TH JH QH KH AD 2D 3D 4D 5D 6D 7D 8D 9D TD JD QD KD AH 2H
right (pt): 3S 4S 5S 6S 7S 8S 9S TS JS QS KS AC 2C 3C 4C 5C 6C 7C 8C 9C TC JC QC KC AS 2S

Permute the red pile. Remove the zenith + 1 card:
            +                                      *
 left (ct): 3H .. 5H 6H 7H 8H 9H TH JH QH KH AD 2D 3D 4D 5D 6D 7D 8D 9D TD JD QD KD AH 2H
right (pt): 3S 4S 5S 6S 7S 8S 9S TS JS QS KS AC 2C 3C 4C 5C 6C 7C 8C 9C TC JC QC KC AS 2S

            +                                      *
 left (ct): 3H 5H 6H 7H 8H 9H TH JH QH KH AD 2D 3D .. 4D 5D 6D 7D 8D 9D TD JD QD KD AH 2H
right (pt): 3S 4S 5S 6S 7S 8S 9S TS JS QS KS AC 2C 3C 4C 5C 6C 7C 8C 9C TC JC QC KC AS 2S

Insert the card into the nadir:
            +                                      *
 left (ct): 3H 5H 6H 7H 8H 9H TH JH QH KH AD 2D 3D 4H 4D 5D 6D 7D 8D 9D TD JD QD KD AH 2H
right (pt): 3S 4S 5S 6S 7S 8S 9S TS JS QS KS AC 2C 3C 4C 5C 6C 7C 8C 9C TC JC QC KC AS 2S

Permute the black pile. Move the top card to the bottom:
            +                                      *
 left (ct): 3H 5H 6H 7H 8H 9H TH JH QH KH AD 2D 3D 4H 4D 5D 6D 7D 8D 9D TD JD QD KD AH 2H
right (pt): 4S 5S 6S 7S 8S 9S TS JS QS KS AC 2C 3C 4C 5C 6C 7C 8C 9C TC JC QC KC AS 2S 3S

Remove the zenith + 2 card:
            +                                      *
 left (ct): 3H 5H 6H 7H 8H 9H TH JH QH KH AD 2D 3D 4H 4D 5D 6D 7D 8D 9D TD JD QD KD AH 2H
right (pt): 4S 5S .. 7S 8S 9S TS JS QS KS AC 2C 3C 4C 5C 6C 7C 8C 9C TC JC QC KC AS 2S 3S

            +                                      *
 left (ct): 3H 5H 6H 7H 8H 9H TH JH QH KH AD 2D 3D 4H 4D 5D 6D 7D 8D 9D TD JD QD KD AH 2H
right (pt): 4S 5S 7S 8S 9S TS JS QS KS AC 2C 3C 4C .. 5C 6C 7C 8C 9C TC JC QC KC AS 2S 3S

Insert the card into the nadir:
            +                                      *
 left (ct): 3H 5H 6H 7H 8H 9H TH JH QH KH AD 2D 3D 4H 4D 5D 6D 7D 8D 9D TD JD QD KD AH 2H
right (pt): 4S 5S 7S 8S 9S TS JS QS KS AC 2C 3C 4C 6S 5C 6C 7C 8C 9C TC JC QC KC AS 2S 3S

Repeat for "H", "A", "O", "C", "I", "P", "H", "E", & "R".

When you are finished keying the deck with the key phrase "CHAOCIPHER", you should have the following order for the red and black piles:

            +                                      *
 left (ct): 6D JH 7D 8D 9D 2D KH JD QD 2H 3H 6H 7H 8H 9H TH QH AD KD AH TD 3D 4H 5H 4D 5D
right (pt): 4S AS 3S JS 5S 7S 9S QS AC 2C 3C 4C 6S 2S 6C 8S 7C 8C KS TS 9C TC JC QC KC 5C


Initialization Vectors

One thing that we have learned with modern computer encryption primitives is to prepend initialization vectors to the ciphertext. The initialization vector must be random and unpredictable. However, its function is to create a unique state on the system before the plaintext is encrypted or before the ciphertext is decrypted. The point is to modify a secret state (our key, or pile orders) while ignoring the output. By adding an initialization vector to the system, we limit the effectiveness of attacks on the ciphertext. For example, if the initialization vector is 26 characters long (one character for each character in the English alphabet, or 26! total combinations), then 25 collisions on one initialization vector to launch an attack on the state (the last element can be determined by process of elimination).

Unfortunately, a 26-character initialization vector is not very practical to use by hand. Knowing that it is standard for field agents to break up their messages into blocks of five characters, it would seems reasonable to use a 5-character initialization vector. However, this doesn't seem to mix the state well enough.

For example, consider using an unkeyed deck to encrypt the text "AARON" 10 times with different initialization vectors at each round:


The first five characters in each ciphertext is the initialization vector, randomly generated. The second block of 5 characters is my name encrypted after the initialization vector keyed the deck. Notice that the first character in the second block seems to have a lot of "V"s and "W"s. If I do 100 rounds, and count the frequency of the first character, I get the following:

F:1, L:1, G:3, K:3, T:4, I:7, J:7, U:7, H:8, W:14, V:45

That is not a good distribution of characters for the first plaintext character being an "A" over 100 different initialization vectors. I would expect it to be much more diffuse. So, how about instead of a 5-character initialization vector, we bump it to 10? How does the frequency distribution look then?

A:1, I:1, U:1, V:1, X:1, Z:1, T:2, E:3, G:3, N:5, O:5, Q:5, B:6, C:6, F:7, D:10, S:11, R:13, P:18

That's a little bit better. A 26-character initialization vector would certainly show a flatter frequency distribution for the first ciphertext character in the message. However, as mentioned, that's cumbersome. So, at this point, it's up to you. Using a 5-character initialization vector would provide about 10 or 11 possible first ciphertext characters. Using a 10-character initialization vector increases that to about 18 with a flatter distribution.

PKCS#7 Padding

As mentioned, it has become a field cipher standard to separate your ciphertext into blocks of 5 characters. This means that if your message is not a multiple of 5 characters, to add padding at the end until it is. However, when the recipient decrypts the message, it should be unambiguous exactly what is padding, and what is not. The padding in PKCS#7 makes this possible.

We can define this easily enough be determining exactly how many characters must be added to pad the message into multiples of 5 characters. So, we'll count:

  • If the message needs only one character appended, append a single "V".
  • If the message needs two characters appended, append "WW".
  • If the message needs three characters appended, append "XXX".
  • If the message needs four characters appended, append "YYYY".
  • If the message is already a multiple of five characters, append "ZZZZZ".

By using the padding described above, after decrypting the message, the recipient needs to only look at the last character to determine exactly how many characters make up the padding, and to strip from the plaintext.

To illustrate this, let's take an unkeyed deck, add a 5-character initialization vector, and encrypt the message "ATTACK AT DAWN". This message is only 12 characters, so I would need to add "XXX" at the end of the message according to the definition above. This my message becomes (removing spaces) "ATTACKATDAWNXXX". Adding the 5-character initialization vector "KEQPN" then encrypting, I get the following result:

plaintext: ATTACK AT DAWN
initialization vector: KEQPN
padding: XXXX


Of course, decrypting "KEQPN XLHTT PRUCA FHUEC" and removing the initialization vector "KEQPN" will reveal "ATTACKATDAWNXXX". It's clear to the recipient that "XXX" is padding, and can be stripped without affecting the plaintext.


This has been a lengthy post, and I commend you for reading this far. The Chaocipher is an interesting algorithm, and I'll be studying its properties as time moves forward. I think the Chaocipher fits well as playing card cipher, and gets as close to "bare metal" as you can without designing an actual mechanical mechanism with two rotating disks and removable character tiles. Playing cards are easy to carry around with you in your pocket, so its portability is nice.

Further, we can increase the strength of the algorithm, as mentioned, by adding an initialization vector at the start of the message, and by adding padding, we can stick with the standard of 5-character blocks in our ciphertext. Of course, this means adding 6-10 additional characters, but for a 160-character message, this doesn't seem too cumbersome.

There are some things that I have observed while using playing cards for the cipher hardware. First, encrypting and decrypting are slow. It takes me about a minute to encrypt/decrypt two-three characters. So, for a 160-character message, it could take the better part of an hour to work through.

Second, due to its slow speed, you may get tempted to try and speed things up a bit, so you can work through the message more quickly. However, this drastically opens you up to mistakes. I was encrypting the plaintext "JELLY LIKE ABOVE THE HIGHWIRE SIX QUACKING PACHYDERMS KEPT THE CLIMAX OF THE EXTRAVAGANZA IN A DAZZLING STATE OF FLUX" over and over. After about 10 ciphertexts, I wrote a Python script to automate the process for me. Only 1 of the ciphertexts was 100% accurate, character-for-character. And, unfortunately, 1 ciphertext was 0% accurate, with every character in the message incorrect. However, on the other 8 messages, I seemed to maintain accuracy for about 2/3 of the characters on most messages. Some others, I made a mistake more early on. Regardless, the point is, I was making frequent mistakes, despite my best effort to not do so. Only 1 out of 10 ciphertexts would decrypt cleanly. It might be worth having two decks, one for producing the ciphertext character, and one for double-checking your work. Of course, this slows you down further, but could be doable for minimizing mistakes.

However, the Chaocipher with playing cards is a fun cipher to work, and easy once you get the hang of it. I would recommend using plastic playing cards, such as the ones from Kem, Copag, or Bicycle Prestige. This way, the cards don't get gummed up like paper cards, are washable, last longer due to their extra durability, and overall, just are a better feeling playing card.

If you work the Chaocipher with playing cards, let me know what you think.