Password Encryption -- Short Answer: Don't.

First, read this.    Why passwords have never been weaker—and crackers have never been stronger.

There are numerous important lessons in this article.

One of the small lessons is that changing your password every sixty or ninety days is farcical.  The rainbow table algorithms can crack a badly-done password in minutes.  Every 60 days, the cracker has to spend a few minutes breaking your new password.  Why bother changing it?  It only annoys the haxorz; they'll be using your account within a few minutes.  However.  That practice is now so ingrained that it's difficult to dislodge from the heads of security consultants.

The big lesson, however, is profound.

Work Experience

Recently, I got a request from a developer on how to encrypt a password.  We have a Python back-end and the developer was asking which crypto package to download and how to install it.

"Crypto?" I asked.  "Why do we need crypto?"

"To encrypt passwords," they replied.

I spat coffee on my monitor.  I felt like hitting Caps Lock in the chat window so I could respond like this: "NEVER ENCRYPT A PASSWORD, YOU DOLT."

I didn't, but I felt like it.

Much Confusion

The conversation took hours.  Chat can be slow that way.  Also, I can be slow because I need to understand what's going on before I reply.  I'm a slow thinker.  But the developer also needed to try stuff and provide concrete code examples, which takes time.

At the time, I knew that passwords must be hashed with salt.  I hadn't read the Ars Technica article cited above, so I didn't know why computationally intensive hash algorithms are best for this.

We had to discuss hash algorithms.

We had to discuss algorithms for generating unique salt.

We had to discuss random number generators and how to use an entropy source for a seed.

We had to discuss http://www.ietf.org/rfc/rfc2617.txt in some depth, since the algorithms in section 3.2.2. show some best practices in creating hash summaries of usernames, passwords, and realms.

All of this was, of course, side topics before we got to the heart of the matter.

What's Been Going On

After several hours, my "why" questions started revealing things.  The specific user story, for example, was slow to surface.

Why?

Partly because I didn't demand it early enough.

But also, many technology folks will conceive of a "solution" and pursue that technical concept no matter how difficult or bizarre.  In some cases, the concept doesn't really solve the problem.

I call this the "Rat Holes of Lost Time" phenomena: we chase some concept through numerous little rat-holes before we realize there's a lot of activity but no tangible progress.  There's a perceptual narrowing that occurs when we focus on the technology.  Often, we're not actually solving the problem.

IT people leap past the problem into the solution as naturally as they breathe. It's a hard habit to break.

It turned out that they were creating some additional RESTful web services.  They knew that the RESTful requests needed proper authentication.  But, they were vague on the details of how to secure the new RESTful services.

So they were chasing down their concept: encrypt a password and provide this encrypted password with each request.  They were half right, here.  A secure "token" is required.  But an encrypted password is a terrible token.

Use The Framework, Luke

What's most disturbing about this is the developer's blind spot.

For some reason, the existence of other web services didn't enter into this developer's head.  Why didn't they read the code for the services created on earlier sprints?

We're using Django.  We already have a RESTful web services framework with a complete (and high quality) security implementation.

Nothing more is required.  Use the RESTful authentication already part of Django.

In most cases, HTTPS is used to encrypt at the socket layer.  This means that Basic Authentication is all that's required.  This is a huge simplification, since all the RESTful frameworks already offer this.

The Django Rest Framework has a nice authentication module.

When using Piston, it's easy to work with their Authentication handler.

It's possible to make RESTful requests with Digest Authentication, if SSL is not being used.  For example, Akoha handles this.  It's easy to extend a framework to add Digest in addition to Basic authentication.

For other customers, I created an authentication handler between Piston and ForgeRock OpenAM so that OpenAM tokens were used with each RESTful request.  (This requires some care to create a solution that is testable.)

Bottom Lines

Don't encrypt passwords.  Ever.

Don't write your own hash and salt algorithm.  Use a framework that offers this to you.

Read the Ars Technica article before doing anything password-related.