How to encrypt (almost) anything

You're a checkbox away from encrypting Outlook email.

Encrypt your email

Your email messages can contain some very sensitive information, which makes them a prime candidate for encryption. If you use Outlook, keeping your correspondence secure is easy.

Outlook encryption is not password-based. Instead, everyone who wishes to use cryptographic security features in Outlook receives a digital certificate, which serves to automatically encrypt and decrypt messages. Before two users can send each other encrypted messages, they must share their certificates by sending each other digitally signed messages. It sounds sort of complicated, but the process is actually straightforward, and takes only a few moments. To set up Outlook for encrypted messaging, follow the steps in the official Microsoft guide.

Once you’ve received and exchanged digital IDs, you can send an encrypted message by opening the new message window, clicking Options > More Options > Security Settings, and checking the box for Encrypt message contents and attachments.

Protecting Gmail messages involves a different approach.

Encrypt your Gmail messages

Email security is a little different when you're using Gmail, as the messages are stored on Google’s servers rather than on your local machine. When you compose or view email messages, they transfer over an encrypted HTTPS connection, so you don’t have to worry about their being intercepted. Really, your primary security risk with Gmail is that somebody else will gain access to your account—a risk you can minimize with good password practices and two-step authentication.

If you want to send a text email that absolutely nobody but its intended recipient can read, you can always use a browser-based encryption application to encrypt your message manually. Email the cyphertext (encrypted text) to the recipient, and then use some other channel to send the recipient the password—they can then use the same Web app to decipher the message.

Password-protecting Office docs is painless.

Encrypt your Word, Excel, and PowerPoint documents

In Office 2010 and 2013, you can encrypt any Word, Excel, or PowerPoint document the same way: Click File, make sure that the Info tab is selected, and then click the Protect Document button. Finally, click Encrypt with Password, and choose a strong password for your file. Anyone who wants to access this file will need the password. As always, it’s not safe to send the password through the same channel that you use to send the file.

Adobe offers plentiful security settings for PDF files.

Encrypt your PDFs

Like the Microsoft Office products, Adobe Acrobat X Pro makes encrypting a file easy. The option is in the Tools tab at the upper right, in the Protection section. Click the Encrypt button, and then click the option labeled Encrypt With Password.

You're one step away from encypting an Evernote note.

Encrypt Evernote notes

The cloud note-taking app Evernote is a great way to remember and organize important information, including account details, medical and financial records, and other sensitive data. If you feel uncomfortable leaving all that personal info out in the open, you should be relieved to know that Evernote has a built-in encryption feature. Simply open a note, highlight the text you want to hide, and right-click it. In the menu that pops up, select Encrypt Selected Text, and then create a password. Evernote hides the selected text, replacing it with a small lock icon. Whenever you want to view the text again, just double-click the icon and enter your password.

TrueCrypt can protect any kind of file.

Encrypt anything else

Finally, I'm going to talk about a way to encrypt pretty much anything at all on your PC: TrueCrypt. A free, open-source application, TrueCrypt lets you encrypt any file or collection of files on your PC. If your personal or business PC has a variety of sensitive documents that you want to protect, this is probably the best option for you.

To use TrueCrypt, first download the program, and then run the installer. The default installation options are fine, so just click through to the end.

Next, run TrueCrypt and click the Create Volume button. A window will pop up to walk you through the volume-creation process. On the first two screens, leave the default options checked and click Next. On the third screen, you’ll be asked to specify a volume location. This is where the encrypted data is going to be stored on your hard disk, so choose a location and a name that will be easy for you to remember. To specify the location, click Select File, which will open a file-browser window. Unlike with most file-browser windows, however, here you type a name into the Name field, and then a file of that name will be created for TrueCrypt to use.

The next screen asks for encryption settings; the defaults are acceptable, so click Next. After that, you’ll be asked to specify a volume size. All the files that you want to encrypt will have to fit into the volume, so make sure to allocate enough space. If you’re storing just text documents, 500MB might be enough, but if you’re storing lots of media, you’ll want several gigabytes at least.

In TrueCrypt, set up a password to protect your data.

Now you’ll be asked for a password—so pick a good one! Finally, after selecting a password, you will be able to finish the process. Follow the instructions on the final screen, and click Format.

Now that your volume is created, you can use it to store files. In TrueCrypt, click Select File, and choose the volume file you just created. Then, click a drive letter and click Mount. After you enter your password, TrueCrypt creates a virtual drive, and the rest of your computer treats it as if you had just plugged in a real hard drive. You can access it as you do any other drive: by opening the file explorer and clicking its drive letter at the left.

Drag whatever files you want to encrypt onto the virtual hard drive; when you’re done, click Dismount in TrueCrypt. The files you stored in the virtual hard drive are encrypted and stored inside your volume file. When you want to access them again, simply run TrueCrypt and mount the volume file just as you did earlier.

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