Monthly Archives: October 2015

Bootstrapping with secure passwords

2 minutes, 6 seconds

I recently fat fingered the partitions on my 5k iMac when installing Ubuntu (more on Ubuntu on a 5k later!), so I was stuck doing a double clean install of both OS X and Ubuntu.  Given how often I find myself re-installing a system from scratch, I’ve gotten pretty good at getting all my core apps set up.  All the software I run is open source or free, so downloading it is quite easy.  But how do you log in using all your secure passwords?  The passwords are stored in my password safe, but the password safe is stored in a password protected, self hosted cloud file server. Classic chicken and egg scenario.  Here’s how I get around it:

  1. Go to a computer where you have your password safe handy
  2. Log into your cloud file server
  3. Generate an unprotected shared link to your password safe.  This will look something like this:
  4. Then take that link, and use a URL shortener to make a short, but not too guessable URL

Now, when you need to bootstrap a new computer, it’s simple as pie:

  1. Download password safe binary
  2. Go to
  3. Download password safe file

Thus we solve the chicken and egg problem.  As well, since we’re pointing to the most up to date version of your password safe on your cloud server, you’ll always have your latest passwords!

Yes, yes, we are exposing our selves here to some risk that some one will guess the shortened URL of our our password safe.  However, this is pretty unlikely that it’ll be guessed.  As well, you use a good pass phrase on your password safe, right?!

For smart phones, I’ve had similar problems bootstrapping when I can’t download the password safe app because I can’t log into the app store. Another chicken and egg!  Here’s how I work around this (which would work for the desktop scenario too):

  1. Turn your phone on, skip account set up
  2. Connect to WiFi or cellular data so your mobile browser can connect to the internet
  3. On another computer, where you have access to your password safe, copy your primary login for your app store (aka your iCloud or gmail/google app login)
  4. Go to and create a secret URL
  5. Go to ye’ ol’ URL shortener, and create a customized, short URL: linking to your onetimesecret URL
  6. Now you can manually type the short URL on your phone and get the password which you can then copy and paste to log into to the phone/app store.

Though it seems like a number of painful steps they both go more quickly than you think and I seem to do them enough they’re second nature.