The Password Conundrum – Part 2

Another picture of a padlock because… passwords?

This is the second part of a three part article on password and account management. In this part, I’ll be going over password manager programs, using strong passwords, and multi-factor authentication.

Password Managers

Password managers are programs that allow people to store all of their usernames and passwords in an encrypted database. This allows people who use password managers to remember just one password – the master password to the password manager program. When the user of a password manager wants to log into a site or service, the user fills in their master password and the password manager software makes their user name and password for that site available to them. This also means that users can make their passwords ridiculously long, random, and complex because they don’t have to remember them. The features and capabilities of password managers vary from program to program. Here are a few options that I considered for my own use:


KeePass is a free, open source password manager. User’s log in information is stored in a local database that is secured using the very strong AES and Twofish encryption algorithms. This means that it would be very difficult for an attacker to steal your usernames and passwords, even if the attacker was able to pilfer a copy of the database file that contained them.

There are several free mobile apps that access your KeePass database using Dropbox. The advantage to keeping your KeePass database in Dropbox is that you can then use KeePass on any computer or mobile device that you have a Dropbox synch folder set up on. There is a portable version of KeePass  that can be loaded on to a USB thumb drive which would allow you to use KeePass on a computer running most versions of Windows. KeePass is available for most Windows, Linux, and Mac operating systems.

Please keep in mind that KeePass is free, so there is no support number to call if something doesn’t work right. If your database file becomes corrupted, or you lose your master password, you’re on your own.


1Password is a password manager that costs about $50. There are versions available for Mac, Windows, IOS, and Android. Like KeePass, 1Password allows you to make your password database available to multiple computers by placing it in a Dropbox sync folder.

There’s a really neat feature that 1Password users who are using 1Password in conjunction with Dropbox can take advantage of. If you are using a computer that is not your own and you need to access a password stored in 1Password, you can do so by logging into your Dropbox account and browsing to your 1Password folder. The 1Password folder contains an HTML file that you can open and once you supply your master password, you can access your log in information saved in 1Password.

There are browser extensions for most popular browsers (Chrome, FireFox, Safari, etc..) which allows users to automatically fill in user names and passwords and other information for sites, so that users don’t have to copy and paste that information from the 1Password program.


LastPass is a full featured password manager. There is a free version and a premium version. Both versions use 256-bit AES (currently very strong) encryption to encrypt your user names and passwords. LastPass uses it’s own service, instead of Dropbox to make your user names and passwords available to you over multiple computers and mobile devices. LastPass uses your computer or mobile device to perform the encryption so the password database that gets saved on LastPass’ servers cannot be read by anyone else – not even LastPass employees.

There are versions of LastPass available for Windows, Mac, and most popular Linux distributions. It’s also available for most mobile devices including IOS, Android, Blackberry, and even *shudder* Windows phones.  There is also a version of LastPass that works on a USB thumb drive. I should mention here that one of the major differences between the free and premium versions of LastPass is that you have to have the premium subscription (a whopping 1$ per month) to use LastPass with most mobile devices.

Another thing that really stands out to me is that LastPass works well with multi-factor authentication, which is something I’ll be covering in more detail later. LastPass works with the Yubikey and with Google Authenticator.

Strong Passwords

ComplexPWPassword strength or complexity describes the quality of a password based on how long it is and how many different types of characters are in it. For many years, popular wisdom was that a good password was at least eight characters long and as long as there were symbols, upper, ans lower case letters and numbers.

Turns out that a person doesn’t have to use a password that contains numbers, symbols, and other assorted characters in order for it to be “secure”; the password just has to be long enough. As a password increases in length, the time and processing power required to crack or guess it, increases exponentially. This is where a pass-phrase comes in. A pass-phrase is basically just a password that is made up of multiple different words. For instance, a good pass-phrase would be “Cannon poke monkey eyes”. The folks over at XKCD explained it very well in this comic:

“Most people use passwords. Some people use passphrases. Bruce Schneier uses an epic passpoem, detailing the life and works of seven mythical Norse heroes.” – Jesse McGrew

Multi-factor Authentication

A factor of authentication is something unique that a person knows, possesses, or is. Factors of authentication are used to confirm that a person is who they claim to be and are commonly used when a person logs into a computer or website. An example of single-factor authentication would be a password. The problem with having a password as a single-factor of authentication is that a password can be guessed, or stolen, or cracked (un-encrypted).

Introducing another factor of authentication (in addition to a password) such as a user’s fingerprint makes it much more difficult for another person to access your accounts and services without your permission. When Twitter’s multi-factor authentication option is turned on, a user must supply a user name and password to log in as well as a code that Twitter sends in a text message to the user’s phone. More and more, websites like Twitter are embracing multi-factor authentication.

Some security-minded folks over at have compiled a list of websites and services that work with multi-factor authentication. Multi-factor authentication isn’t infallible but it is generally much more secure than just using a password. I highly recommend considering taking advantage of multi-factor authentication to further secure your accounts.


Okay, if I haven’t totally lost your attention yet, we’re in good shape. This part of the article was by far the largest and most in-depth part of the series. Next up, the third and final part of the series in which I talk about how I used each of the concepts discussed above to improve my own security practices.


The Password Conundrum – Part 1

Obligatory password-blog-post lock picture. We can all breathe easy now that the status quo has been upheld.


This is the first part of a three-part article in which I’ll discuss managing online accounts and password security. In this first part, I’ll talk about the embarrassing state of my own account management – or lack thereof, what prompted me to get my act together and form a realistic account management strategy, and a brief note on what my personal needs for account and password management entail.

In the second part of this article, I’ll go over some of the tools and strategies that I researched while I was figuring out how I was going to manage my accounts. I’ll cover password managers, using complex passwords, and multi-factor authentication.

In the third part of this article, I’ll discuss my overall account management strategy: what I did and didn’t do, and also my rationale behind each choice. I hope that by the end of this article, you’ll have a good idea of what is available to help you get your accounts under control and to also make informed choices regarding what methods and technologies that you want to use to help keep your accounts and personal information secured.

A shameful tale of woe and regret

I’ve been an Internet user for about half my life now. That’s been enough time to collect many, many accounts. I have at least 3 email accounts, accounts on the usual social networking sites, and a slew of random accounts for online stores and services. I figure that I have somewhere around 30 personal accounts that I’ve set up over the years. There are many others that I’ve lost track of, consigned to the briny depths of the web to be forever forgotten.

It’s time for a confession dear readers: I have committed a grievous evil. I have re-used passwords for multiple personal accounts with wild abandon. On top of that, before this article, I had not changed passwords on some accounts for years. What’s worse is I know better than this; I follow best practices for passwords in my professional life obsessively. Seriously, there was an intervention and everything. I guess it would be at this point where I’d say something about the cobbler’s son having no shoes.

This was pretty much the extent of my super sophisticated personal password scheme. Luckily, I kept the post-it note under my keyboard where no one would ever find it.

Continuing down this cliche’d path, I’ve heard that people don’t change until the pain of staying the same is greater than the pain of changing. For me, the pain came just a few days ago when I received an email from The email stated that they’d been compromised and that the attacker had gained access to their database of usernames and encrypted passwords.

I have an account on Had I used the same username and password on that I used on other sites? I couldn’t remember. *CRAP*! Time to put my big boy pants on and get this password mess sorted out.

First, I had to figure out what sites I had accounts on. I started a list of all of the sites I could immediately recall, then I went through my archived emails and found several more sites. I have A LOT of accounts.

Over the years I had halfheartedly skimmed many articles (like this one) that provided advice on proper account and password management. All these questions started popping into my brains: Should I set up a password manager? Which password manager should I use? How complex does my password need to be? How can I set up multi-factor authentication and how well does it work?

It was about this time that I started to become overwhelmed. I needed to do some reading. I researched and read way too many articles and blog posts and here is the strategy that I found would work for me. Others may not have the same security needs, so, as always keep in mind that YMMV.


I spent some time thinking about what my needs were and how I access my accounts. I use a variety of computers and devices. I have multiple beat up, old computers running Windows and Linux based OSes in varying stages of obsolescence, an iPhone, and a broken iPad which I may replace in the distant future. I access email and other accounts from my own, trusted systems and other’s that I don’t trust.

It would be nice to be able to access my various accounts easily and securely, regardless of the computer or device I am using. I need to be able to remember my passwords. At the very least, the passwords for my most important accounts – Email, banking, etc. need to be different from each other. Services like Linkedin, Dropbox, and Twitter get “hacked” with some regularity, so being able to easily come up with secure, memorable passwords without repeating old ones is a necessity too.

So this concludes the first part of my three-part password conundrum saga. Check back soon for part two where we dive into the tools, methods, and concepts behind building a solid account/password management strategy.