Are Your Passwords Safe? (Part 2)

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How to remember passwords

As I’ve said, the best way to ensure that you never forget your passwords is to offload the task of remembering them to a password manager like 1Password. Most of the time, that’s the only trick you’ll need. But no matter what tools you use, you’ll have to memorize at least a few passwords. Because those are among your most important, you don’t want to trade security for memorability. Here are tips that can help you make sure your brain doesn’t betray you.

Pick which passwords to memorize

I have no idea what 99 percent of my passwords are. They’re long strings of random computer-generated characters. When I need to use them, I let my password manager fill them in for me, or I copy and paste them if necessary.

Pick which passwords to memorize

Pick which passwords to memorize

However, one password I’ve memorized cold is the one that I use unlock all of the other passwords stored in my password manager. I’ve also memorized my OS X user account password, because I enter it many times a day; and since I use OS X’s FileVault, I need that password to start up my Mac before I can access any automated tools. Also, I’m frequented prompted to enter the passwords for my iCloud, Gmail, and Dropbox accounts, so I’ve memorized those, too.

Your list might differ, but most people can get by with committing no more than half a dozen passwords to memory.

Choose a path to high entropy

Once you know which passwords you need to memorize, your next job is to choose passwords that are strong enough to defeat automated hacking attempts yet memorable enough that you can produce them instantly and for bonus points, they should be convenient to type.

Your next job is to choose passwords that are strong enough to defeat automated hacking attempts

Your next job is to choose passwords that are strong enough to defeat automated hacking attempts

You undoubtedly know the basic drill: All things being equal, longer passwords are better than shorter ones; random passwords are better than those that follow a pattern; and the best passwords combine upper- and lowercase letters, numbers, and symbols. It turns out, though, that a password doesn’t need to possess all of those qualities in order to be secure; for example, a long but simple password can be just as secure as a short but complex one. This is provable through a concept called entropy, which in this context, refers to the mathematical approximation of how difficult a given password is to guess.

Depending on how you perform the calculation, the passwords 7H#e2U&dY4 (ten random characters) and blanketsensory (14 nonrandom characters) are approximately equal in strength, but the latter is much easier to remember and type. Even though it contains only lowercase letters, and blanket and sensory are both ordinary English words, the password’s entropy is high enough that a concerted brute-force attack would take days or weeks to crack it.

If your memory is excellent and limiting your passwords to the fewest possible characters is your biggest consideration, then go with a shorter random password – but remember that whereas short used to mean eight or nine characters, nowadays using 12 to 14 keystrokes is safer. Nevertheless, since most people can type long words faster than short bursts of random characters, you may find that a 25-character phrase is more convenient to enter in daily use than a 12-character string of nonsense,

Let a computer pick your passwords

I’ve sometimes advised people to use mnemonic cues to remember passwords. For example, taking a sentence such as “I once drank three cups of coffee before realizing it was decaf,” and using just the first letter of each word, with a capital and a number thrown in, creates Iod3cocbriwd – a reasonably strong password. But because humans unconsciously tend to introduce patterns into passwords produced through these means (which makes guessing the password easier), I let a computer create a selection of random (but memorable) passwords, and then I choose one that sounds good. You have numerous ways to do this.

They’ve sometimes advised people to use mnemonic cues to remember passwords

They’ve sometimes advised people to use mnemonic cues to remember passwords

If you open Keychain Access on your Mac (in /Applications/ Utilities), choose File ð New Password Item, and click the key icon next to the Password filed, a Password Assistant window will appear. Choose Memorable from the Type pop-up menu, and select a password length. The utility will produce a password consisting of a combination of words, numbers, and symbols (such as nineteenth8590.middlingly or baiting325@certifications). Don’t like the first suggestion that you see? Click the pop-up menu to generate more, or choose More Suggestions from that menu to get another list.

1Password’s password generator also has a mode that creates a series of pronounceable syllables (not necessarily English words), with or without intervening digits or hyphens – such as liegnicroci, lieg7ni2croc5i, or lieg-ni-croc-i. To generate them in the 1Password app, choose File ð New Item ð New Password, click Pronounceable, and select the separator and length that you prefer. Click the Refresh button to see another password choice. (The directions are similar when you’re using 1Password’s browser extensions, although the layout and options are slightly different.)

Have backup plans

If you’re afraid you’ll forget your memorable passwords, you can write them down, as long as you keep that paper in a safe place. Your wallet might be a fine location (indeed, security expert Bruce Schneier recommends it []). Also, consider giving a copy to your spouse or a trusted friend, or putting it in a safe deposit box. If something happened to you, and your family or business associates urgently needed access to your data, the security of storing your passwords only in your head would work against you.

  •  10 Contenders For The 'Ultimate Protector' Crown (Part 5) : Microsoft Security Essentials 4.1, AVG Antivirus Free 2013
  •  10 Contenders For The 'Ultimate Protector' Crown (Part 4) : Norton Internet Security, Avast Free Antivirus Version 7
  •  10 Contenders For The 'Ultimate Protector' Crown (Part 3) : Eset Smart Security 6, Kaspersky Internet Security 2013, Zonealarm Internet Security 2013
  •  10 Contenders For The 'Ultimate Protector' Crown (Part 2) : Bitdefender Total Security 2013, Trend Micro Maximum Security, Mcafee Internet Security 2013
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  •  The Slithery World Of Hybrid Cloud Security
  •  SharePoint 2010 : Planning Your Security Model - Maintaining Your Security Model
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