Some more iPad security tricks…

by Richard Riehle

I have been looking for ways to secure and to encrypt much of the information I keep on my iPad…I’ve been looking since I got it. In the last month I see the beginnings of some baby steps in this effort to make the iPad a real, serious platform for real work, for business, and for the needs of increasingly sophisticated users.

I say baby steps in that using a four digit passcode to open the iPad is not what is not what I would call strong security…but it is a start. As such I have started using this simple way to control my stuff from basic theft (you should too…).

Similarly with DropBox (an incredibly important add-on for any iPad) there is a reasonable need to deal with some simple encryption. I have tried using TrueCrypt in DropBox and find that while it is a fine tool for PCs, on DropBox it is far too cumbersome to use for anything larger than a couple megabytes. Using SecretSync is looking to be a valid interim way to control what I keep in the DropBox cloud.

How to take the extra step to secure your iPad’s data

When you establish a secure passcode on your iPad, the expectation is that no one can access any information without knowing said code. There are cases where this is not necessarily true. In fact, any user account on the Mac that you use to sync your iPad can fully access all of the data stored on your iPad without knowing the passcode, including the Guest account.

IPad passcode configuration

Even though it isn’t 100 percent foolproof, securing your iPad with a passcode is a good first step for security. On my iPad 2, I configured security to use the longer alphanumeric passcode, and I make sure that it will lock the iPad immediately when the cover is closed by doing the following:

  1. Open Preferences and navigate to the General settings.
  2. Set Auto-Lock to 2 minutes.
  3. Turn the Passcode on and set require Passcode to “Immediately.”
  4. Turn the Simple Passcode off.
  5. Turn Erase Data On to wipe the iPad after 10 failed logon attempts.

After you sync your passcode protected iPad with your Mac, you should notice that any user account on that Mac can still access the data on your iPad using any of the following methods. Attach that same iPad to any other Mac that has not accessed any data on that iPad in the past, and you will get an error indicating that the device is protected with a passcode.

How to Add a Second Layer of Encryption to DropBox

If recent security and privacy concerns about Dropbox make you think twice about using the popular file storage and syncing tool, there’s an easy way to further protect your sensitive files stored on Dropbox: yes, we’re talking about encryption.

TrueCrypt is our go-to data encryption tool and no doubt you know we have a thing for Dropbox, but although we’ve briefly mentioned using TrueCrypt as one of the clever ways to use Dropbox, we’ve never fully married the two. It’s about time.

How to Encrypt Your Sensitive Data on Dropbox

Windows program SecretSync provides an easy way to encrypt a local folder before sending it to Dropbox. You install the app, it creates a new folder on your computer, and anything you place in that folder is automatically encrypted and then synced with Dropbox. It’s actually quite clever.

If the idea of securing your cloud data by putting your trust in yet another cloud service is too much, you could instead encrypt your data yourself with the cross-platform, open-source encryption application TrueCrypt. Essentially you’d manually encrypt your files, and then store your encrypted files on Dropbox. It won’t be as easy to share or work with individual documents encrypted with TrueCrypt as non-TrueCrypt-encrypted files, but even Dropbox itself recommends using TrueCrypt for your most sensitive documents.